Octanol-Water Partition Coefficients of Simple Organic Compounds James Sangster ‘Sangster Research Laboratories Suite M-3, 1270 Sherbrooke St. Wes, Montreal, Qubee, Canada H3G 1H? Received ly 21, 985 revised manuscript eeived January 30,1989 ‘Octanol-water partition coefficients (Iog P) for 611 simple organic compounds repre senting all principal classes have been retrieved from the literature. Available experimen- tal details of measurement are documented from original articles. Pertinent thermody- namie relations are presented, with a discussion of direct and indirect methods of ‘measurement. Reported log P data for each compound have been evaluated according to stated criteria, and recommended values (with uncertainty) are given ‘Key words:octanol-waterpattion coeficient; organic compounds; hydrophobicity; hydrophilicity Contents List of tables. 1111 2. General characteristics of some measurement List of symbols and abbreviations. M111” and estimation methods for P ms 1. Introduction 1112 3, Partition coeicients of alkanes M24 1 11124, Partition coefficients of alkenes and alkynes... 1123 1112 5, Partition coefficients of aromatics. 1125 1112 6 Pantiion eveticiens of eyeloulkanes and ey- LL, Need for critical evaluation 1113 cloalkenes ma 1.2. Thermodynamics 11137, Partition cosfcients of mixed-type hydrocar- 12a. General equilibrium relations we 113 bons 1143 126. ‘Temperature dependence 11138. Partition coefcients of ethers seme 1144 1.2. Specific thermodynamic relations .. 11139. Partition coeficients of alcohols. 1150 2. Methods of measurement. 1116 10, Partition coefficients of aldehydes 1163 2.1. Direct or “Experimental” methods 1116 11, Partition coficients of ketones 1165 2a. Shake-flask 1116 12. Partition coefcients of acids 1170 2.L.b. Generator column 1116 13. Partition coefficients of esters. un 22, Indirect or "Caloulation/eorralation”™ 14, Partition cocfiientsofhelogenatedcompounls 1105 methods 1117 15. Partition coeficients of amines 1192 22. Methods widely used and/or having 16. Partition coefcents of nitriles wns 1216 some theoretical justification 111717, Partition coefiients of nitro compounds um 1219 22b. Other correlations een 1117 18. Partition coefcients of amides 1221 3. Comparison of methods of measurement or est- 19. Partition coeficients of sulphur compounds... 1225 mation 1117 20, Partition coefficients of other compounds wu. 1226 + Reuieval oPdata ny 5. Criteria for evaluation 118 6 Presentation of data in Tales 3-20. m9 7, References... m7 List of Symbols and Abbreviations List of Tales ee 1. Temperature dependence of Log Pot some com- as Stsorpton spectropotomety pounds at room temperature. m3 FP Pte, & eat npc at onstant pressure © 1989by the US, Sereary of Commerce on bealfof the United Stats CR chemical reaction “his copyright i assigned tothe American Iie of Phys and the D et method ‘American Chemial Sci FL ‘iuresence ‘Reprints avalble fom ACS; see Reprints Lista back of sve 6 Gib emery (0047-2680/80/091111-120/812.00 nn 4. Phys. Chom. Ret. Data, Vol. 18, No. 3, 19801. Introduction 1.4. General ‘1a. Detintion ‘A pure substance may distribute itself between two par- tially miscible solvents in intimate contact, and the equilibri- ‘um ratio of solute concentrations in the two phases has come tobe known asthe distribution coeficient or partition coei- cient! In preparative organic chemistry, the use of solvents ‘of greatly difering polarity (e-., hydrocarbon and water) facilitates the extraction and purification of desired prod- ucts, In addition, the biological activity of simple organic ‘ampoule wa early found to.correlate with thai ol- water partition coeficients.” It became apparent that, for biologi- cal purposes a partition coefficient based on long-chain ester ‘or alcohol solvents was more appropriate. After some delib- eration, I-octanol was chosen as the most useful lipophile solvent in these applications. Most correlation work has ‘been done using the octanol-water par, and thsisthereason for ito wide we aud che eibteuve Ura great yuanty OF dat ‘om the subject. The octanol-water partition coefcient ofa substance X ata given temperatures, hy peneralconsent,| represented by P and defined by (for reasons explained later, the super- scripts “org” and “aq” are used to denote mutually satu- rated phases, and “oct” and “w” for the pure solvents.) Pa(XPVEXTS, a ic, the ratio of concentrations (mole/volume) a equilbr- tum: itis therefore unitless. In the interest of standardization and precision in interpretation, the partition coeficient is ‘defined forthe same species on both phases." This is impor- tantin considering Pofionizable compounds such s organic Phys. Chem. Ret. Data, Vol 18, No.3, 1989, JAMES SANGSTER x = mote fasion x ate ; ttl Lag Pate; Code uncertain Gi a ' siterencein thermodynamic function y solame ction stv cotient & Shamil potential @ lame esction é = saublty mal! Petal strated water phase = standard tate recat ent ph ‘phase saturated withsolue ure water phase = Hanch Leo “selected” Log Pale ‘= apparent (partion coset) acids, amines, and quatemary ammonium salts, which may also form dimers or ion-pairs. This is discussed further in this Introduction. Inaddition, the solvents represented in Eq, (1) are those ‘mutually caturated with each other at the temperature of ‘measurement. This is a natural consequence of the classical “shake-flsk” or extraction method used in experimental ‘measurement of P, and is tobe taken into account for accura- cy in measurement and thermodynamic interpretation. Further, Pis preferably defined as the quantity which is independent of concentration, i, that value for which the solute obeys Henry’s law in both solvents simultaneously. In practice, this means a P determined at high dilution, or ex- trapolated to zero concentration. Since P as measured can range over many orders of magnitude (10-? to 108), i ie usually expressed as its decadic logarithm, log P. 1.4. Scope of this evaluation ‘This work proposes to have retrieved and evaluated moot of the significant published experimentally determined values oflog Pof simple organic molecules. The word “sim- ple” istaken here to indicate molecules containing no or only fone polar functional group, ic., a group having N,O,S and/or halogen atom. A few well-known exceptions (chlor- oform, CCl, ) have been included. This limits the mumber of substances involved and, as far as possible, avoids complic tons of interpretation due to the presence of neighboring polar groups. The compounds are those which are liquids or solids at ordinary temperatures and pressures, and no arbi- trary upper carbon number cutoff limit has been imposed Elements, inorganic, metal-organic and unstable species hhave been excluded, as well as quaternary ammonium and similar salts.OC TANOL-WATER PARTITION COEFFICIENTS OF SIMPIF ORGANIC COMPOUNDS. 1.8 Need for etc evtuation “The pattion cosficent, a8 properly defined, i a dei tne equilibrium physico-chemical property ofa pure sub- “tance under specified conditions. It provides a useful quan- wative parameter for ing. the lipophilio/ Indrophilic nature ofthe substance. It sa function of the ibs energy of transfer from water to octanol and hence ckscribes the thermodynamic tendency forthe compound to ion preferentially in diferent media. Tis not surprs- therefor, that it has been widely used in many areas such as --design of drugs and pharmaceuticals.‘ prediction and correlation of bioconcentration® ‘and soil and sediment sorption of organic pollutants, -rescarch on medicinal chemicals, “modelling of environmental fate of organic chemical,” toxicology of substances. For many substance, log P has been measured by dif facut Iaburatorice ead by diferent methods. The reported log Pralues ofa single substance can sometimes vary a great deal for example those of pp-DDT cover arangeofa factor of one hundred.* Large uncertainties in loz Pare undesirable in general, The accuracy ofthe simulation, by calculation, of ‘he envizonmental fate of an organic chemical may become quite sensitive to uncertainties of input parameters (eg, ‘Mirexin Lake Ontario"). The successful development of a¢- ditive-constitutive calculational schemes for log P, based ‘on molecular structure, requires a database of assessed accu- racy. Finally, it is difficult, if not impossible, for the unini- tiated user oflog P datato distinguish sccurate and inaccur- ate data by simple inspection. 1.2 Thermodynami ‘The thermodynamic relationships between log P and ‘other quantities will be examined in some detail in this sec- tion. Many experimental data on log P related thermody namic quantities have appeared recently, some of high quali- ty. Since these were not discussed in any detail in former coumpiladiouy and reviews"? the following eapusition is ‘meant to summarize the important thermodynamic rela- tions in a concise and rigorous manner. 1.2 General equilibrium relations ‘The present thermodynamic analysis is slightly edited -eotatoment of the one currently being used to deverbo the two-phase system represented by the octanol-water partition cocficient*"™9™ Like the current practice, it uses vol- ume fractions as composition variable and volume fraction activity coeficients. This convention, when used in conjunc- tion with the (volume-based) partition coeficient, simpli- fies the thermodynamic argument. An equivalent though in- complete, analysis using mole fractions is given elsewhere.” If liquid substance Xs distributed between ‘organic and aqueous phases at equilibrium, we can write for cach phase? Br=Hr + RT Inay Q) HALF RT ICY 92) @) 1113 ‘where is the chemical potential of Xin solution is the chemical potential of pure liquid X, ay sit activity in slu- tion, 7 isthe volume-fraction activity coefficient and gy is the volume fraction of Xin the solution, From the defining Eqs. (2) and (3), the activity coefficient is normalized by alwgy—l. ‘By definition, in each phase we have Lhe= 90 o where V isthe (pari) molar volume of X in solution. (For dilite solutions of liquid nonelectrolytes in water or cctanol, partial molar volume canbe replaced by pure liquid ‘molar volume without appreciable error.) At equilibrium, HF" = uP. Combining this equality with Eqs. (1), (3), and (4) yield? Wap P= Were o i.e, Pis equivalent tothe rato of the Henrian activity oefi- cients of the solute in the phases. Equation (5) has been derive using tse ansuunption dat PP — FE 1.20. Temperature dependence “The variation of log P with temperate! ie emall, op proximately 4001 K', Table 1 presents experimental data of d(log P)/dT for some specific compounds. ‘The thermodynamic transfer functions are closely re- lated to log P: O.G= —RTInP (6) A, @/dt= —A,S o A,G=A,H—TA,S @ ‘Asa consequence of the definition of P, these transfer quan tics are independent of concentration and refer to the dif ference: (function for solute in water-saturated octanol)— (Function for solute in octanol-sturated water). The temperature dependence of A,.G and hence of log Pan berepresented by 4, and A.,S through Eas. (6), (7), and (8). A van't Hoff plot of in P may be used to obtain ‘Tanus | Temperature dependence of Log Pf some compounds at room Teapentrs lO ab H/AT Ret ‘4.Phys. Chem. Ret. Data, Vol 18, No.3, 1989,114 enthalpy and entropy of transfe.""* However, Pis a Gibbs energy function—as are solubility and vapor liquid equilb- ‘iuin—and these functions are usually found tobe relatively insensitive to temperature. The enthalpy of transfer may be more precisely determined either by direst experimental measurement in an isoperibol flow calorimeter (in which ‘wo immiscible phases are brought into direct contact) or indirectly from the calorimetric limiting enthalpies of solu- tion in the two solvents separately. ‘As willbe discussed in greater detain the next section, both 4, Gand 4, may be determined from measurements ‘n solutions based on the two solvents separately. Ths is a possible route, provided itis realized tha solute thermody= ‘namic functions in pure water or pure octanal maybe signif- cantly different from those in mutually saturated solvents. 1.24 Specie thermodynamic relations ‘Mutually saturated solvent. From liquid-liquid equilibrium data” the equilibrium mole fractions of octanol inthe two-phase system water/n- ‘ctanol at 25°C are 7.03% 10? and 0.793. Saturated oc- tanol thus contains an appreciable amount of water; the mo- Jar volume of wet own ts 120.0 cm’, and the water content is equivalent to 1.64 mol L', The two phases in a shake-lask determination of P are ternary. The question whether or nat the presence of the other solvent ina phase significantly alters the thermodynamic properties of the sol ue becomes important in considering recently elaborated “activity coefcient” methods of determining the partition coeficent. For example, Bert etal compared the transfer Gibbs ‘energies from shake-flask log P values of some common so- Its to those found fiom dhe dieeily measured Hearian activity coefficients of the same solutes in pure octanol and pure water. The differences in &,,G, 1 to 2 kJ mol~?, is equivalent to differences of ax much as 4 0.4in tg P, being negative or positive or zero, depending on the solute. Calor- ‘metrically determined enthalpies of transfer of m-alkoxy phenols*in neat and mutually saturated solvents dilfered by 1p to 1.6 KJ mol~'; the same effect is found in the eorre- sponding enthalpies of solution” from which the transfer enthalpies are derived. Agsin, the magnitude ofthe effect ‘depends onthe solute; the transfer enthalpies of n-alkanols™” for example, are much less sensitive in this respect. Platford™™” used the isopiestic method to measure the Limiting activity coaicients of CCl, and benaene in nest and ‘mutually saturated solvents, and found no detectable difer- ence in the results. Henrian activity coefficients in octanol for 22 monofunctional compounds were measured by gas chromatography; within experimental error the relation Pa ry was valid Relationship with aqueous solubility. ‘Thermodynamic considerations have also elucidated the relation between log P and aqueous solubility, early proposed by Hansch etal Since both log P and ¢ may be regarded as Gibbs energy transfer functions, an equation of the type ‘4. Phys. Chem. Ret, Data, Vol. 18,No. 3, 1980 JAMES SANGSTER log P= mlogé +m 10) mightbe expected tobe valid where m and n are correlation coefficients. A relation lke Eq. (10), if true, would greatly reduce the experimental effort necessary to obtain P. The search for refinement and rationalization of Eq. (10) has been lively, givingrac to atleast one polemic exchange the literature." ‘A relation of the form of Eq. (10) can be derived from thermodynamic frst principles.» The case fora liquid sol- tte wl be given rst, asa solid solute introduces a complica- tion into the argument. For a liquid solute distributed at equilibrium between organic and aqueous solvents (The sol- ‘vents are assumed tobe mutually saturated, inorder to keep the analysis as close as possible tothe conditions in real shake fask situation.) Eq. (3) can be applied to both phases, tose (e298 = (102) hich, by Eq, (4) becomes XD = (FX. «ay (Consider now, asa separate system, the solute in saturation cauilibrum in the aqueous solvent. On the assumption thet the equilibrium free solute contains no solvent, Eq, (3) un- der these conditions becomes 18 + RT ING) ay My 3) (ng) = 1. aay ‘Combined with Eq, (4), this becomes (rata ¥a" = 1, as) ‘where ey has units inverse to that of Vy. Recalling Eas. (1) and (5), PaXTVXI = B a6 Introducing Ea. (15), PH=WU(YECRV er) (7) logP— logs logtre Mx)" aig) Eq, (18) has the same form of Eq, (10). Cleary, data for liguid solutes would all fall ona common linea plot oflog P sw log, with the following provioe: ‘ASSUMPTION 1:7 the Henrian activity coeficient {or liquid solutes in organe solvent, is the same forall solutes. ASSUMPTION 2: refers to water saturated with oc- tanol. ASSUMPTION 3:the solute obeys Henry’slaw foreon- ‘centrations up to saturation in the ‘aqueous solvent. ASSUMPTION 4:the fee liquid solute, as an equilibr- ‘um phase, contains no solvent (i, its activity is unity). Forsolutes which are solid at temperature of measure- ‘ment, fundamental equations such as Eq. (2) are valid. In this case, however, the reference stat for # cannot be the ‘pure soli, since itis desirable to keep the same Reoult's aw convention forthe activity coeficients. The approach is thenOCTANOL WATER PARTITION COEFFICIENTS OF GIMPLE ORGANIC COMPOUNDS through solid-liquid equilibrium. For a component in equi- librium between solid and liquid phases, Bes) =H), aay HR (8) + RT In ag(s) =HY(1) +RTInag(1), (20) HRC) — HHS) = RT In ay (s)/ay(1)- an “The quantity onthe left-hand side of Eg. (21) isthe Gibbs energy offusionofthesoluteat temperature T, AG. Ithe equilibrium solid phase is pare soli, then Sew G= — RT In ay (1), @ For temperatures below the normal melting point ofthe sol- Ute, Ag refers to the process (solid~supercooled lig- uid) Since the solution i saturated, em = RTI)" on ‘The thermodynamic argument represented by Eqs. (12)~ (18) can be repeated again, with Eq (23). The result is op P= — bn 9/2203R7 = beady = los (7%), ro) Eq, (24) is the same as Eq, (18), with the addition ofthe ‘Gibbs energy of fasion term. The’vaidty of Eq. (24) i of course subjettothesameassumptionsattached tog (18). For correlation purposes, the Gibbs energy’of fusion to the supercooled liquid state may beeapresed i tes of he usual fusion quantities: — bu G/RT = (eH /2.30BR)(T = Tous)/ TT $+ (By, C$) (I(T /Tiyg) + (Ting — T/T). (25) 1n Bq, (25), the enthalpy and heat capacity quantiles refer to corresponding changes at the normal melting point (Tua). [The heat capacities of solid and liquid solute have theen assumed to he independent of temperntice. They are not soin general, and Eq (25) could be modified to take this {nto account.} Eqs. (24) and (25) together are identical 10 Eq, (14) of Miller etal Eq, (25) may be simplified by putting By, Cp =O and Aga = Ty, Bry S® = 56.5Ty Tmol~'. The results an expression equivalent to Eq. (26) of Mackay ef a.” ‘Apart Mom these smplincation, the rour assumptions quoted above are of varying importance. The Henrian activ- ity coefcient in octano, 77", has been estimated by indi rect and direc" mathode. Iie slr, partioalaly for hy Arophobic compounds, that this activity coefficient increases with molecular weight (or molar volume). The water solubility, isusually taken as that in pure water. The solubilities of organic compounds in octanol-saturated wa- ter are measurably diferent.*°*” The difference increases ‘with molecular weight. Its dificult at present (ifnotmpos- sible) wo define precisely the individual errors introduced into Eqs. (18) and (24) by these assumptions and simplii- cations > Ratio of solubilities thas been stated that Pis equivalent to the ratio of solute solubilities in the two solvent,* or is well approxi- mated by this ratio.” The thermodynamic justification for 1146 liquid and solid solutes is derived from Eqs. (1), (15), and (22) for the case of two phases saturated with solute. The results PHSB RRLEICE (26) As before, the important qualifying assumptions apply here also. There may be some fortuitous cancellation of effects. Yalkowsky etal.” have tested Eq, (26) using solubilities in neat solvents for 36 solid compounds and found reasonable, though not exact, correlation, Henry’ law. ‘The Henry's law constant, likelog Pisa limiting Gibbs energy quantity and its usetulness overlaps that of log P." Henry's constant fora solute on the mole fraction scale, Hy, ‘may be defined as" (where is the mole fraction of solute) an ‘where pis the partial pressure of solute above the solution, ‘enrian penavior of solutes as been exploited” in tne “head-space gas chromatographic method” for measuring P. The principal feature of this methods the sampling and ‘hantitative analyse, by gae chromatography, of the vapor ‘mixture above a liquid solution. In a measurement of P, the vapor above an unsaturated aqueous solution (volume, of the solute is sampled and the gas chromatographic peak height (i, ) of the soluteis obtained. A volume of octanol is added, and after equilibration the vapor is sampled and analyzed as before (/,). The partition coefcient is then P=vi(hi/hz— Dios (2s) Equation (28) assumes that Henry's law is obeyed by the solute in the aqueous phase; that Hj, is independent of the presence of co-solvent; that there is & strict mass balance for the solute; and the vapor behaves ideally. lim(p/x) = Hy 1.8. The ease of lonizable eolutee In the present work, two types of organic compounds ‘may ionize in aqueous solution, viz., acids (HA) and amines oy HASH™+A-, a) BHY=B+H", (30) where 4~ is the acid anion. [Water should appear on both sides of Eqs. (29) and (30), but since in dilute solution its activity is practically unity and does not change, it may be From the thermodynannic aualysin] The Urcssnady= ‘namic dissociation constant isdefined as = a(H*)a(A~)/a(HA) an after Bq. (29), and K, = a(H*)a(B)/a(BH*) (2 after Ea, (30). Since Pis defined only forthe same (undisso- ciated) species in both phases, the apparent partition coefi- Cient Pip (Sometimes called distribution coeficient) mea- sured in the presence of appreciable ionization according to Eqs. (29) and (30) will dtfer from P. It.can be shown™ that Page and P for an acid are related by P= Pap [1 + 10°92] aa ‘Phys. Chem. Ret. Data, Vol. 18, No.3, 1989,1116 JAMES SANGSTER, and for an amine by Mixing and separation. P= Pall + 10°") a Several different methods of agitation are used to For weak ais (pK, >7) or weak bases (pK, <7) in water, there is negligible ionization (Pre, =P). For other com: pounds under some experimental Sonition, there wl be Sppreciableioniation. [For example, phenol isa very weak acid (PK, = 939) and isnot appreciably ionized in neutral ‘olution. For patachlorophenol, however, th alcoholic by- ‘oye atom rendered more able sured values of? over the pH range 1 than thre orders of magnitude In thes 88, Pap may be corrected aoording to Bae (33) and (14), or beer of Suitable pH may be used as the aqueous phase in order to Suppress ionization. Some compounds (eg. acids) may form dimers or other associated species inthe organic phase ‘Ts sore of err may be avoided bythe se of suficenty Values of P reported inthe literature have been deter- ined by many methods. Mention is madein thissection of suet large number ofthese, but only the more reable oF soundly based will be discussed in some detail. For the pur- poses of evaluation, the methods have been clasifed into {wo groups (direct and indirect). This division fe made for convenience of discussion, and doesnot necessarily imply fundamental o far-reaching theoretical differences. 2.1. Direct or “experimental” methods 2.1. Shake-fask method This classic extraction procedure is widely used and, ‘with due attention to experimental conditions, manipulation and range of applicability produces reliable results. It has ‘been described briefly and necessary precantions haveheen discussed in some detail The case of weakly ionized so- utes hasbeen given special attention.*”In essence, the meth- od is simple. A small amount of the solute is dissolved in either aqueous or organic phase, equilibrium partition is ob- tained by agitation, the phases are separated and one or both phases are analyzed for solute. Apart from requirements al- seady mentioued in See 1 of this seview, a few of dhe utes important precautions may be mentioned here. Purity of chemicals. ‘Depending on the analytical method used, the presence of parttionable impurities in solvents or sample may lead to erroneous measured solute concentrations. Mutually saturated solvents, tis often the practice i this method to prepare a solu- tion of known initial solute concentration ¢, in one solvent, and equilibrate a definite volume v, of this with a definite volume v, ofthe other solvent. The final solute concentra tion ¢, is measured in the first solvent and the partition coeficient is given by the ratio (¢,—¢,)0,/ jy OF its inverse. Since the densities of neat octanol and ‘water-saturated octanol are measurably different, the use of| presaturated solvents avoids any error through changes in solvent volume upon equilibration. 4 Phys. Chem, Ret. Data, Vo. 18, No.3, 1989 the solvents into intimate contact. In general, prolong violent shaking isnot necessary and tends to cause emt formation. The phases separate under normal gravity they are usually centrifuged to accelerate the separati the smallest droplets. ‘Sampling. ‘Ideally, both phases are analyzed. This isnot a done, for reasons of convenience and time. Ifonly one is analyzed, a mass belance between the phases is ass and it must be established that no solute has been le adsorption on glass, rubber stopper or other uiaesial manipulation. Since many solutes preferentially par into the organic phase, care must be taken to ensure sampling devices introduced into the phases da nat ina tently carry over one phase into the other. Analysis. ‘Absorption spectrophotometry and gas-liquid matography are often used. There may be intermedia traction and/or concentration steps, or one involv chemical reaction. The usual precautions in quanti ‘analysis apply here Volatile solutes. Ifthe solute hasan appreciable vapor pressure itm ‘necessary to consider the amount of vapor space in the libration vessel and details of manipulation during samy analysis, etc ‘Since the shake-lask method is at times tediow: ‘ime-consuming, a number of automated or simpli sions have been used. Most are closed-loop low deviet counter-current distribution (engineering des Centcfngnl partition chromatography? may scribed as the addition of a high gravity field t counter-current method. -The AKUFVE system” uses continuous centri tion to separate the phases, while the rapid mix, probe?" uses different membrane filters. -the segmented flow device" isa miniaturized cot current now system. three-phase partition system” isa kind of cot current method using two aqueous phases: AQVORG/AR, Where AQ, and AQ, are diferent aqueous br ‘This device is used principally fr investigating | ies of partition, -the exponential concentration change method” ‘be regarded as a multi-step extraction procedure 2.1. Generator column method ‘The ordinary liquid chromatographic column ¢ hhae been adapted for the measurement of partition « cients."="' The solid support is usually silanized dias ceous silica. The column is loaded by pulling an unsat solution ofthe solute of interest ata known concentrat water-saturated octanol through the column. The sol luted with octanol-saturated water, and the effuent it lyzed by high pressure liquid chromatography or gas—)UGIANUL-WAIEH PAH IITION GUEFFIGIENTS OF SIMPLE ORGANIC COMPOUNDS ‘omatography. A primary advantage of this design'®is the cence of any possibility of emulsion formation, since the ents are brought into intimate contact by slow permea- 1 of one through the other. It sa closed system and ma- ulation is minimized it is a low system and so interior faces in contact with solute in sokution may be ‘‘condi- ted”, ifnecessary, without affecting accuracy. 2.2. Indirect or “Calculation/Correlation” Methods 1. Methods widely used and/or having some theoretical Tustifeation ‘The deduction of P from aqueous solubility and Hen- saw constants has been discussed in Sec. 1.2.. Probably ‘most widely used correlation method is that with solute :ntion volumes or chromatographic capacity factors in ersed-phase high pressure liquid chromatography (RP- LO) The possiblity of obtaining a single general ‘pose correlation has been extremely seductive, as evi- ced by the large number of published attempts and de- cd investigation of the interacting effects among solute arity, eluent composition and chemical nature of the sta- rary phase.” The attempt cannot be described as totally cessful, despite recent refinements such as coating the Jonary phase with octanol” * or dipalmitoyl phosphati- choline and use of e-hydroxy siice™ as column pack- ‘eappears that satisfactorily precise correlations are ob- ted when the results are extrapolated to 100% water 9s int or when homologous series plots are used."*® The ‘hod is easily automated." Reverse-phase thin layer chromatography (RP- (©) may be considered the two-dimensional analogue AP-HPLC. The precision of RP-TLC, including a chemi- xy modified version,” is generally inferior to RP-HPLC. ‘For weakly ionizable solutes, a potentiometric tiation ‘hod has been used.” Sometimes called microelectrome- titration, this procedure yields values for both Pand K, ingle experiment. Equations haveteen piven for difune- ral acids” and a completely automated version has been cribed.“* An analogous thermometric titration proce- ‘based on the enthalpy of protonation of an amine, has > been used.” ‘A statistical analysis for a correlation between loge- ims of octanol-water and cyclohexane-water partition co- ints was carried out by Seiler” for 230 compounds. A sar relation was found, and th intercept included aterm resenting hydrogen bonding by the solute. The same re- + was obtained for more accurate data" of homologous ies with octanol-water and hexadecane-water solvent rs and predicted from a lattice-model theory.** ‘Henrian activity corficints ofa solute in both solvents hence P, may be calculated by the UNIFAC (UNI- 'AC Functional Group Activity Coeficients) group con- ration model”*7*2; the presence of co-solvent is easily resented in the calculation. ‘The additive-constitutive nature of log Pis property 2n displayed by many physico-chemical quantities. This ‘ect as been successfully exploited” in the invention of aur two fragment constant additivity schemes forlog P. Thetwo methods, while similar, are not identical and differ some- ‘hat in accuracy, applicability and ease of use.®” Hansch and Leo's method! has been packaged as an interactive com- puter program (CLOGP).”* In a somewhat more elaborate version (MOLY),” the user draws the molecular structure on a graphics terminal 2.2.p, Other correlations: Both Hansch and Leo's’ and Rekkers' fragment addi- tivity schemes tend to be inaccurate for compounds with multiple halogen substitution. A nonlinear function has ‘been devised for multply-subsituted aromatic and hetero- cyclic compounds. A number of other quantities with which og 7 has been correlated are listed here. -solute retention indices on twostationary phases in gas chromatography" (useful for volatile solutes) -solnte molar vohime!* “solute molecular surface area”™®" charge density"? -solvatochromic parameters!” molar refraction"* -solvent-dependent conformational analysis (SCAP)** -parachor'**” = membrane cell potentials" elution times for adsorption on Tygon tubing" -molecular connectivity” 3. Comparison of Methods of Measurement or Estimation ‘When one or more log Pvalues of substance ae ava able toa user or evaluator who wishes to place an uncerta tycon the single value, or deduce the most probably accurate value, the following considerations are pertinent: (3) the ‘method of measurement or estimation used, together with any available experimental details, ii) the perceived compe- tence of the measuring laboratory or investioatr. (ii) the date ofthe measurement. Knowledge ofthe general charac- teristics of methods of measurement of published P values is necessary for evaluation, even though their usefulness may ‘be qualined by consiaerations (i!) and (im) above m certain cases, Table 2 presents characteristics of some direct and indirect methods. Useful discussion is available, along wi some tabulated results of intra and inter laboratory a surements by different methods.""°" The consequences ‘of the various considerations in Table 2 are discussed in Sec. Slow. 4, Retrieval of Data ‘The basis ofthe literature search was the Pomona Col- lege log P Database, created and maintained by Prof. ‘Hansch and Leo. It is the most complete compilation ofits kind, available online (Technical Database Services, Inc.,10 ‘Columbus Circle, New York, NY 10019) and updated twice yearly. The version of July 1987 was used for the present work. For January 1987-June 1988 the Subject Index of (Chemical Abstracts was used to ensure a more complete 4 Phys. Chem. Ret Data, Vol 18, No. 3, 186918 Matos (SF) Geserntor 207 Genera except Directmathad Column bone rip stim (8) forveryhydrophiic_Nodarperofemason ‘fel ‘sepoands ‘Coed ten ‘New enum sede fice temperate ‘echohte ‘al init bpp Fasrthan SF ‘omyouns Rather cborte analyte equipes Revere pase ows Nea species ast, conveicat Cortina tic biphgresue baud ‘ote Impriendonst Sp coceton (HPLC) Analysis ot oquied Watersaaiity 2w6 Neat peciesot Convencat Cottons metic ‘oration Tmiedwater ——Hasthomodyoamic bass Spe coreltion ‘oly incre ‘enn acs Depenas wpe Netra spe nermogynamicaly ate of mentrement coats rostetoaciity ‘act curacy depends op ‘occa route acy ‘oficent Pragmestal Same SF Fas, convenient Requires exe conan Relablefor meals completed lea! ‘ith ot many por Ube onl fr fn pou Boupe coved in che coverage. During consultation of original articles, a number ‘fother useful seferenees were found sid were incorporated into the present compilation, Forevery log P datum of compounds investigated, the “orisinal iterature reference was consulted. whenever aval- ble; in the case of direct methods of measurement, the fol- lowing information was retrieved (its importance has been pointed out recently™): empernture of messurement -equilbration method analytical method aqueous phase (water, ber, ete.) “Which phase(s) was analyzed -if no details were given but a reference was made 10 ‘another publication, this was noted and the informa- ‘on retrieved, 1k was decided to include also a number of log P values obtained by indirect methods, since these are useful for eval- tution and, at times, are the only reports available. (Of course, the original articles did not always contain ‘any oral the information sought, but whatever was avail- able was retrieved. The source of a number ofthe data inthe ‘Fomona College Database are unpuDUsed results trom, oF private communications to Dr. Hansch and Dr. Leo. No ‘experimental details are available concerning these dat; in 4 Phy. Chem. Ret Data, Vol 18, Ne. 3, 1008 the present evaluation they are classed as direct mes rms, No log P values calculated frm fguent cot appear in the compilation, although estimates by Hansch and Leo and Rekker methods were used occasi 1s ais in evaluation, Inthe case of ionizable compo the log P value given by the author or in the Datab whether corrected for ionization or not—vas recorde data were corrected by the present evaluator. 5. Criteria for Evaluation ‘The evaluator wishes to have as many aids and to ‘canbe found; the number and power of these tols vat ‘cording to the subject in hand. For example, in the cr ‘evaluation of binary phase diagrams," available excess ‘modynamic data and other thermodynamic consti ((Gibbs-Duhem equation, phase rule, ec.) provide rk ly stringent and objective guidelines to data evaluatio. the case of P, however, most of these constraints ar applicable, and the thermodynamics of solute distribut ‘inadequate at present to provide such constraints.** On} ‘Gioos energy of alstnbution is Well summarized in the ‘ve fragment constant schemes; the corresponding ent! ‘of distribution data are, however, absent for the mostOCTANOL-WATEH PAHTITION CUEFFIGIENIS UF SIMPLE URWANIG CUMFUUNDS: Wherever both direct and indireet methods are repre- ted in the log P valucs for a given compound, more ight is given to those from direct methods. When neces- Y or possible, directly determined values are further ighted by the availability of experimental details. In the ‘mona College Data Base—and also inthe present compi- ‘on—Hansch and Leo's selected values are indicated by asterisk. This isa valuable guide in evaluation. In some a recently determined (Or redetermined) value by di- {method under optimum conditions is deciding factor. oubiful eases where the spread in reported valuesis wide, ‘20 direct determinations are at hand, it is helpful to.con- cr simultaneously the value from fragment constant \emes. The Hansch and Leo method was followed in a thtly simplified version, "and the Rekker method alsoina plified version.” It has been found” that both methods rerally yield similar results, particularly for the simple ‘ecules considered in the present work. 1m those cases Where only an astensked log F valve is vorted, an uncertainty of 10%—considered a fair esti- ‘e”—was assigned. Where the recommended valve fere markedly from experimental vals, this was booasas sre weight was given tolog P from additivity schemes; the certainty is correspondingly larger. Based on these considerations, a recommended values, ‘en for each compound, together with an uncertainty in parentheses. This uncertainty is neither simply the Wc totl range ofall cored values, Rather it ep isthe range in which, in the evaluator’s judgment, the ve valve lies. Thus the uncertainty may be large when only # reported datum exists, and smaller according to the mber and consistency of reported data. It should be clear m the discussion to this point that theres always an irre- cible minimum of arbitrariness in this kind of evaluation ‘dard deviation of all recorded values nor does }. Presentation of Data in Tables 3-20 Retrieved data for 600 simple organic compounds are ‘sented in these Tables according to chemical type: Table No. Chass of compound om ‘ie ‘ ‘Alkenes and alkynes 5 ‘Aronatice é {Cetoatkanes and cytothenes : scesype nyarocaroons 4 Ethers 5 Alcohols 0 ‘Aldehydes 2 ‘eile 8 Bates “ Hageman 6 Nites 0 [Nitro compounds i ‘Amiser 8 Soiphor compounds 2» Otter thin each table, the general order is by increasing carbon mber, then by increasing number of hydrogen atoms. ‘mers are listed in increasing degree of branching, and in aw the order of primary, secondary, and tertiary compounds. ‘The only exception to these rules is in Table 13 (Esters) ‘where the esters are listed according to the parent acid, Formic acid, n-propyl ester Formic acid, phenyl ester Acetic acid, methyl ester Acetic acid, ethyl ester ete. but the other rules are adhered to. Each compound is identified by, from left to righ, the ‘chemical formula, name(s) and CAS Registry number. The order of elements in the chemical formula is GHN.0,(BiCLEDS. For acids and amines ony, these ate followed by the acid dissociation constant, pK. Unless otherwise noted, these are for 25°C and were taien from ‘were estimated from data for similar compounds or accord- {ng to well established methods". “The seitieved data teanvelves, for excl compound are presented under nine column headings. From left to right Asterisk (*): Hansch and Leo selected value, 2: Doubtful value; CCode-this identifies the type of method used for deter- ‘mination: Dé direct method, 1: indirect method, information insuficient or unavailable; Ref-source of data. Personal communications to, oF unpublished data in the Pomona College Data Base are all assigned to Ref. 104. ‘Temp.where original report mentioned temperature, this is indicated (in°C) MB: temperature quoted as “ambient,” Equi. Method-method of equilibration: GC: generator column SE shake-Hlask; ‘Anal. method-method used for analysis ofthe phases: ‘AS: absorption spectrophotometry, ‘CR. chemieal reaction, FL: fuorescence, GLC: gas-liquid chromatography, HPLC: high-pressure liquid chromatog raphy, K: Kjeldahl analysis for N, RC: Radiochemical, TTI: acid-base titration ‘Aq, phase-nature ofthe aqueous phase: W: octanol-saturated water, 1S: neutral salt solution, pHLxxx: buffer solution of stated pH; Phase(s) analyzed-AQ: aqueous, ORG: organic, ‘one: either aqueous or organic (not specified); Method ref.-investigator’s stated source for method. ‘The indirect methods used to determine log P values ‘Phys. Chem. Ret Data, Vol 18,No. 3, 1889YAMES GANGSTER Auxiliary information is provided in footnotes a HPLC, etc). The D and 1 values are listed in separate end of each table In Tables 19 and 15, in corrected | ‘groups and placed in increasing order within each group. values (reported at source) are footnoted as such, Allo ‘The lat entry for each compound is a recommended log Pare not ion corrected. value, with uncertainty in parentheses. Phys. Chem, Ret. Data, Vol. 18, No. 3, 1988OGTANOL-WATER PARTITION GOEFFIGIENTS OF SIMPLE OHGANIG GUMPOUNDS = 1121 Table 3. Alkanes Equil. Anal. Aq. Phases Method Log P Code Ref. Temp. Method Method = Phase = Analyzed Ref. CgHyz nePentane CAS # 109-66-0 2.50 D 30 SF uc w AQ 46 2.50 oD 105 SF 3.23 D104 ° Both 43.59 D104 Both 3.62 D910 25 G auc Ww Both u Bez 25 ¢ xe w Both ° 3.60 I 58 25 from measured activity coefficients 3.64 I 10 from measured activity coefficients 3.45 (0.20) Recommended C,H,2 2.2+Dimethylpropane (neopentane) CAS # 463-82-1 “3.11 D 104 3.11 (0.20) Recommended Cgtyg —aHexane CAS # 110-54-3 Aa D 941025 G cic Ww Both n an D 58 25 G Guc Ww Both a 3.007 «I a2 hoad-space chromatographic mothod 107 3.90 ete 106) 20 from measured activity coefficients 4.16 I 58 25 from measured activity coefficients 4.20 i 10 25 from measured activity coefficients 4.25 I 22 25 from measured activity coefficients 4.00 (0.25) Recommended Celyy S-Methylpentane CAS # 96~14-0 2907 1 head-space chromatographic method 107 3.60 (0.20) Recommended Cty 2,2-Dimethylbutane CAS # 75-83-2 “3.82 D104 Both 3.82 (0.40) Recommended Cgtg 2.3-DimethyIbutane CAS # 79-29-8 *3.85 D104 Both 3.85 (0.40) Recomended 4. Phys. Chom. Ref Data, Vol 18, No.3, 19801199 Table 3. Alkanes (continued) JAMES SANGSTER Equil. Anal. Aq. Phases Method Log P Code Ref, Temp. Method Method Phase Analyzed Ref. Coty 2»5-Dimethylbutane CAS # 79-29-8 eotss) | | oe Both 3.85 (0.40) Recommended Cig n-Heptane CAS # 142-82-5 Gr66| 6 fe Dies (0.10F 825) G cic W Both 4:66 D $25 6 Gc W Both 3 448 1 2 © 28 from measured activity coefficients as SR (25 from meacired activity rnnfficiants a7 1 at] from measured activity coefficients 4.50 (0.25) Recommended Cythy r-Octane CAS # 111-65-9 Sig) || a0 | as @ cus Ww Both = ita) Sen 25 G Gc Ww Both 9 4.002 1 109 head-space chromatographic method 42,107 S24 58 -25.-—= «from measured activity coefficients 8.29 «I 10 25-— «from measured activity coefficients 5.15 (0.45) Recommended Cgflyg _-n-Nonane CAS # 111-84-2 asl 1 109 head-space chromatographic method 42,107 5.65 (0.60) Recomended Cyoflgg mDecane CAS # 124-18-5 Sram © a 3 21 109 headspace chronatographic method 42,107 6.25 (0.70) Reconmended "Hee 5.648 6.10 n-Dndecana D I 110 109 eas # 117-40-% 6.80 (1.00) Recommended S1a¥50 7.20 n-Tetradecane I 109 head-space chromatographic method 42,107 CAS # 629-59-4 8.00 (1.00) Recommended head-space chromatographic method 42,107 @W. E. Hamers, personal communication 4. Phys. Chem Ret. Data, Vol. 18, No 8, 1980OGTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS 1123 Table 4. Alkenes and alkynes Equil. Anal, Ag. Phases Method log P Code Ref. ‘Temp. Method Method Phase + Analyzed Ref. Cig 1,3-Butadiene CAS # 106-99-0 1.99 D104 Both 1.99 (0.20) Recommended Cyl, 2-Butyne CAS # 503-17-3 1646) s1 1D] 11 104) pou 1,46 (0.20) Recommended Cyl, cis-2-Butene CAS # 590-18-1 "2.33 D104 Both 2.33 (0.30) Recommended CyHy —trans-2-Butene CAS # 624-64-6 2.51 0D 104 Both 2.31 (0.30) Reconmended CyHy --2-Methylpropene (isobutene) CAS # 115-11-7 eae 104 Both "2.400 104 Both 2,35 (0.40) Recommended CH, —-‘1,4-Pentadiene CAS # 591-93-5 *2.48 104 Both 2,48 (0.30) Recommended CyHy -_-1-Pentyne CAS # 627-19-0 Bie). | Di sds) || fag oF auc w one 49 Pate ft) EU) 25 G GLC W Both ul 1,98 (0.20) Recommended Clg -—«*LS-Hexadiene CAS # 592-42-7 2.452 D 104 2.80 (0.50) Recommended 4 Phys. Chem. Ret. Data, Vol. 18,No. 3, 19691124 JAMES SANGSTER Table 4. Alkenes and alkynes (continued) Equil. Anal. Aq. Phases Method log P Code Ref. Temp. Method Method == Phase = Analyzed Ref. Gétg —-«s-Heqme CAS F 695-02-7 @ers 4 aD orld zs 6 cic w Doth n 2.73 (0.30) Recommended Cglg I -Hexene CAS # 592-41-6 3.59 D 9 25 G Guc Ww Both uw 39D 38 2 & GLC W Both 9 3.47 OD 10 25, G HPLC W Both 3.401 58 25 from measured activity coefficients 347 oT io 25 ‘from measured activity coefficients 3.40 (0.10) Recommended CjHyy —‘T-Heptene CAS # 592-76-7 3.99 gn 28 6 ae w Roth 11 399 D8 25 G cic W Both 9 4.05 1 88 25 from measured activity coefficients 5.99 (U1U) Recommended Cythg -*1-Octene CAS # 111-66-0 456 D8 25 G cic W Both 9 “4.57 D 9 25 G cue W Both = 11 #00 D0 23 6 PLC w boul 4m 1 8 25 ‘from measured activity coefficients eG 25 ‘from measured activity coefficients 4.57 (0.20) Recommended Cytyy —-T-Nonene CAS # 124-11-8 5.15 D 9 25 G cic W Both = S15 D 58 25 G GLC W Both 9 5:35 D0 25 6 WLC W Both S31 1 58 25 ‘from measured activity coefficients 5.3400 dT 10 25 ‘from measured activity coefficients 5.15 (0.20) Recommended ‘Phys. Chem. Ret. Data, Vol. 18, No.3, 1989,OCTANOL-WATER PARTITION GOEFFIGIENTS OF SIMPLE ORGANIC COMPOUNDS = 1125. Table 5. Aromatics Equil. Anal. Aq. Phases Method Log P Code Ref. ‘Temp. + Method Method Phase + Analyzed Ref. Benzene CAS # 71-43-2 D 40 25 SF AS pHT.4 Both = 17 D 58 25 6 WLC W Both =I D log a Both D104 D0 Both Dos. SE AS ONS AQ D3. 25 SF aS W Both vy tus 2 Sr KU w Both D 46 25 SF As W AQ Do 25 SF cue W AQ D0 28 e ypc OW D104 D108 Both D104 pH2.7 1 65 HPLC I 33 from water solubility correlation I 58 fron measured activity coefficients I 10 25 from measured activity coefficients I 106 25 from measured activity coefficients 28,29 I 74 25 from UNIFAC activity coefficients I 64 HPLC I 16 HPLC I im HPLC 2.15 (0-10) Recommended CgDg __-Hexadeuterobenzene CAS # 1076-43-3 2.03 oD 1s SF AS ONS AQ 2.03 (0.20) Recommended Cylz Toluene. ~—CAS # 108-88-3 a ee) 25 SF AS pHT.4 Both 117 2.21 D108 3 SE RC Ww Both 2.61 D 15 SF AS NS. AQ Zo3 DY 1. 2 6 WiC OW Both By 2.65 DSB 25 G wie |W Both n 268 =D 18 23 SF WLC OW Both 2699 =D 46 25 SF 4S. Ww ‘AQ "2.73 D104 2.80 oD 104 4 Phys. Chem, Ret, Data, Vol. 18,No. 3, 18881126 JAMES SANGSTER Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Method log P Code Ref, Temp. Method Method Phase Analyzed Ref. CH, Toluene (continued) 251 1 33 25 from water solubility correlation 2.51¢ 1 65 HPLC 2.64 58 25 from measured activity coefficients eo 64 UPLC eon | or 10 25 from measured activity coefficients 2576 a or 4 25 from UNIFAC activity coefficients 2.77 119 Pre. Pay 75 25 from UNIFAC activity coefficients 2.94 12 HPLC 2.9% (0.10) Recenmended Octadeuterotoluene CAS # 2037-26-5 Ay) us SF AS NS AQ 2.57 (0.20) Recommended Cglijg 1,2-Dimethylbenzene (o-xylene) CAS # 95-47-6 eorieat a0) 104 Silsg 2D 9,10 25 G HPLC Ww Both Boy 2770 oD 104 fst04a ae 33 25 from water solubility correlation 3.08 65 HPLC Sica 10 25 from measured activity coefficients 3.12 (0.20) Recommended Cyt _1.3-Dimethylbenzene (m-xvlene) CAS # 108-38-3 3.200 D 104 3.20 -D 9,10 2s G HPLC w Both 1 3.220 «1 65 HPLC Sti 0 10 25 from measured activity coefficients 3.37 57 HPLC 3.20 (0.20) Reconmended Gghhg 144 Dimothylbonsone (p-xylene) CAS # 106-42-5 35 0D 104 3.18 9,10 25 G HPLC,GLC |W Both Bay 3.08, «I 42 head-space chromatographic method 107 salset a 65 HPLC B82. 5 25 from IINTFAC activity coefficients 3.15 (0.20) Recommended 4 Phys. Chem. Re. Data, Vol 18, No.3, 1980OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS 1127 Table 5. Aromatics (contimed) Equil. Anal. Aq. Phases Method log ¥ Lode Ker, ~—lemp. + MeTHOd-sMethod = vase = analyzed Ket. Cyto —-Ethylbenzene CAS # 100~41-1 313 D910 25 G HPLC W Both = 1 3130 D885 G HPLC w Both = 11 45150 D120 SP 4S w 4Q 46 3.07 1 65 HPLC 3:10 1 33 25_—‘from water solubility correlation Buz raz iL 314-158 «25._—«from measured activity coefficients 315 I 10-25 ‘from measured activity coefficients 328 1 75~=—«25._—«from UNIFAC activity coefficients 3.15 (0.20) Recommended ogy Indene ons # ob az 6 *2,92 D108 3.26 I 65 HPLC 2,92 (0.20) Reconmended Colyy —m-Propylbenzenc CAS # 103-65-1 3.44 DB 23 SE HPLC Ww Both 3.57 D104 3.68 D120 SE As. w AQ 46 3.098 = D910 2s G HPLC Ww Both 3.69 D8. 25 G HPLC W Both = 11 ssimb po 25 sT,G 9 IPLC W Both 3.59 I 33 25 from water solubility correlation 3.60 Ta head-space chromatographic method 107 3.69 raat HPLC 3.71 I 58 25 from measured activity coefficients 3173 I 10 25 from measured activity coefficients 3.90 Toi HPLC 3,69 (0.15) Recommended Cgtl,y —‘Tsopropylbenzene CAS # 98-82-8 3.66 =D 108 3.66 =D 104 3.51 Ia head-space chromatographic method 107 3.52 Tu HPLC 3163 1 35 25 from unter entuhility earralation 3.66 (0.20) Recommended «4. Phys. Chem. Ret Data, Vo. 18, No.8, 1989,4198 JAMES SANGSTER Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Method log P Code Ref. Temp. + Method Method = Phase «Analyzed Ref. Cg). 1,2,3-Trimethylbenzene CAS # 526-758 3.55 D 9,10 25 c HPLC w Both a 3.66 I 11 HPLC 3.60 (0.20) Recommended Cyl, 1,2,4-Trimethylbenzene CAS # 95-63-6 Dros DT 10 2 6 HELE W Both 3.58 I 33 25 from water solubility correlation 93.78 I HPLC 3.63 (0.15) Recommended Cgllyz 143,5-Trimethybenzene (mesitylene) CAS # 108-67-8 5,42 ceed) 104 3.840 121 HPLC ais I B 25 from UNIFAC activity coefficients 3.42 (0.30) Recommended C 1-Methyl-2-ethylbenzene (2-ethyltoluene) CAS # 611-14-3 2 3.53 =D 94,1025 G HPLC W Both 1 3.65 42 head-space chromatographic method 107 3.53 (0.30) Recommended Cyl, 1-Nethyl-4-ethylbenzene (4-ethyltoluene) CAS # 622-96-8 3.65 I 42 head-space chromatographic method 107 3.65 (0.40) Recommended Cigllg Naphthalene CAS ¥ 91-20-3 3.01 40 25 er AS pli. Doth 117 3.28 OD 94 SF W AQ 3.50 104 3.35 68 SF GLC w Both 335 10 25 G HPLC W Both 3.36 86 20 SF GLC W AQ 46 3.36 D113 25 SF AS W Both 335700 124 3.40 126 23 SF FL Ww AQ Phys. Chem. Ret. Data, Vol 18, No.3, 1989,OGTANOL-WATER PARTITION GUEFH Table 5. Aromatics (continued) .NIS UF SIMPLE UHGANIG COMPOUNDS = 1129 Log P Code Ref. ‘Temp. Equil. Method Anal. AQ. Method Phase Phases Analyzed Ref. Method Coty Naphthalene (continued) 3.45 D125 SF 3.59 D104 3.17 I 56 HPLC 3:29 I 19 HPLC 52500 aay 33 25 from water solubility correlation 3.50! I 64 HPLC 3.33 1 az head-space chromatographic method 3.43 I 65 HPLC 3.65 I i 25 from UNIFAC activity coefficients 3.35 (0.10) Recommended Cygllg -Azulene CAS # 275-S1-4 3.20 De 1 2108 3.220 «D127 SF AS W ORG 3.22 (0.20) Recommended Cyotg —-T-Rutythenzene CAS # 104-51-8 4.260 D104 4.28 =D 9,10 2s GS HPLC,GLC Ww Both a2 58 25 6 wic’ WwW Both 4.01 I 42 head-space chromatographic method 4.18 I 68 25 from water solubility correlation 434 I 58 25 from measured activity coefficients 44d I qa. HPLC 4,26 (0.15) Recommended Cygll,, tert-Butylbenzene CAS # -98-06-6 407 oD us 23 Sea ric Both “4.11 D104 a1 D104 4.11 (0.10) Recommended Cyghy —- -Methy1-4-isopropylbenzene (p-cymene) CAS # 25155-15-1 “4.10 D108 23 SE RC Ww Both 414 I 4 25 from UNIFAC activity coefficients 4.10 (0.10) Recommended 107 ln i 107 ‘Phys. Chem. Ret. Data, Vol 8, No.3, 19891130 JAMES SANGSTER Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Method Log P Code Ref. Temp. Method Method Phase «Analyzed Ref. Coty 142,3,4-Tetramethylbenzene CAS F 488-25-3 3.98 D 10 28, G UPLC Ww Both “4.1 I aa HPLC 4.00 (0.20) Recommended Cig, —1,2,3,5-Tetramethylbenzene CAS # 527-53-7 4.04 v 20 2 6 HELE " Both “4.17 ra HPLC 4.10 (0.20) Recommended CygH,, 1,2,4,5-Tetramethylbenzene CAS F 95-93-2 *4.00 D104 2.802 1 2 head-space chromatographic method 107 4.24 1 128 Here, 4.10 (0.20) Recommended GyyHyq _{-Methyinaphthaiene CAS # 90-12-0 *3.87 D 126 B SF FL Ww AQ 3.95 I 33 25 ‘from water solubility correlation 3.87 (0.20) Recommended C\,Hjg 2+-Nethylnaphthalene —CAS # 91-57-6 73.86 D126 23 SF iL W AQ ann iD 113) 2 SF aS. Ww yoth 3.90 I 33 25 from water solubility correlation 4.01 I 65 HPLC 4.09 ay 2 219) HPLC 4.00 (0.20) Recommended Cyj)g —_n-Pentylbenzene CAS # 538-68-1 4.90 D 9.1025 G HPLC Ww Both u 4.90 (0.30) Recommended 4. Phys. Chem. Ret. Data, Vol 18, No.3, 1989(OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS, 1131 Table 5, Aromatics (contimed) Equil. Anal. Aq. Phases Method log P Code Ref. Temp. Method Method Phase Analyzed_—Ref. (yyHyg — Pentamethylbenzene CAS # 700-12-9 “4.56 Taz HPLC 4.57 1 123 HPLC 4.56 (0.40) Reconmended CygHyg “Biphenyl CAS # 92-52-4 Selo) | 1D) | a0, as SE AS p74 = Both 117 Si7e§ D2 6 Ge Ww Both = 11 3.89 D129 85 G HPLC W Both er SE sioss in) 10 4.08 D125 SF 1 Ao D108 23 = mmc w Doth 3.63, «I 130 Lc 3.700 oT 4 HPLC 3.75 I 56 PLC 377-16 WLC 3.79 «I 128 HPLC 4.01 I 6 HPLC 4.02 I a head-space chromatographic method 107 408 0 2 BL, 4210 I 68 —-25_—-from water solubility correlation a5 Tong HPLC 414 T3325. from water solubility correlation 42400 7 from solubility ratio 4250 TT 25 from UNIFAC activity coefficients 3.98 (0.10) Recommended Acenaphthene CAS # 83-32-9 D0 SF D108 23 oF RC w oth I 33 25 from water solubility correlation I 4 25 from UNIFAC activity coefficients 3.92 (0.25) Recommended (,H,, 1-Ethylnaphthalene CAS # 1127-76-0 *4,39 D 38 23 SF FL. w 4.42 I 33 25 from water solubility correlation 4.40 (0.40) Recommended 4. Phys. Chem, Ref, Data, Vol. 18,No. 3, 1969a192 Table 5. Aromatics (continued) JAMES CANGSTER Equil. Anal. Aq. Phases Method logP Code Ref, Temp. Method Method © Phase Analyzed Ref. Cty 2-Ethylnaphthalene CAS # 939-27-5 44.38 D126 2B SF FL w AQ 4,38 (0.50) Recommended Cyt 1,2-Dimethylnaphthalene CAS # 573-98-8 “1 D126 23 SF FL W AQ 4,31 (0.40) Recommended Cy 1,%-Nimethytnaphthatene CAS # 575~41-7 “442 D126 23 SE FL Ww AQ 455 1 33 25 from water solubility correlation 4,42 (0.30) Recommended Cyt 1,4-DimethyInaphthalene CAS # S71-S8-4 Sis aD| | 6 23 SF FL W AQ 43900 33 25 from water solubility correlation 4,37 (0.30) Reconmended Cth 41,5-Dimethyinaphthalene CAS # 571-61-9 “4.38 D126 23 SF FL, Ww 4Q 4350 33 25 from water solubility correlation 4.38 (0.30) Recommended Cyt 1,7-Dimethylnaphthalene CAS # 575-37-1 “444 D126 23 SF FL W AQ 4.44 (0.30) Recommended Cty 1,8-Dimethytnaphthatene CAS # 569-41-5 “4.26 D126 23 SF FL. W AQ 4.26 (0.30) Recommended Cyt 2,6-Dimethylnaphthalene CAS # 581-42-0 “4.51 0D 126 23 SE FL Ww 4Q 4320-7 35 25 from water solubility correlation 4.31 (0.50) Recommended 4. Phys. Chom. Ret. Data, Vol. 18, No. 3, 1989OCTANOL WATER PANTITION COEFFICIENTE OF EIMPLE ORGANIC COMPOUNDS = 1188 Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Method log P Code Ref, Temp. © Method Method Phase «Analyzed Ref. CyzH,g - 3Hexylbenzene CAS # 1077-16-53 Guba seep) 9,10 25 Gc HPLC w Both a sted 68 25 from water solubility correlation 5.52 (0.30) Recommended CyyHyg -Hexamethylbenzene CAS # 87-85-4 esl) 104 4.61 10 25 6 HPLC Ww Both 5.00 1 123 HPLC oat 1 da. HPLC 4.75 (0.25) Recommended Cygyg —-“Fluorene (AS # 86-73-7 Gals 0 104 4.18 D 132 SF Gic pH? Both 4.18 D 37 30 SF AS Ww Both 4.18 1 68 25 ‘from water solubility correlation 4:23 1 119 HPLC yk 33 28 from water solubility correlation 4340 «1 37 25 from solubility ratio 4.18 (0.20) Recommended Cystz -‘Diphenylmethane AS # 101-81-5 “4.14 104 4.22 1 65 HPLC 4.14 (0.20) Recommended Cy3hy —$-MethyIbiphonyl CAS -644-08-6 4.63 D 81 25 G GLC Ww Both 129 4.66 «T 19 wie 4.63 (0.20) Recommended CysHh, —-4,4,S-IrimethyImaphthalene CAS # 2131-41-1 4791 33 25 from water solubility correlation 5.10 (0.50) Recommended -4.Phys. Chem. Re. Data, Vol 18, No. 3, 10881194 JAMES SANGSTER Table 5. Aromatics (continued) Bquil. Anal. Aq. Phases Method Log P Code Ref. Temp. + Method Method Phase «Analyzed Ref. Cy 2,3,6-Trimethylnaphthalene CAS # 829-26-5 “4.735 «D126 23 SF A W AQ 4.75 (0.40) Recommended Cyqlyg Anthracene cAS # 120-12-7 “445 D128 SF 445 D132 SF cc pH? Roth 45d D «3 25 SF ‘AS W Both 3.45270 56 HPLC 4.20 I 12 HPLC. 451 I 65 HPLC 4.60 I 64 HPLC 4.65 I 42 head-space chromatographic method 107 4203 I uy HPLC 473 I 33 25 from water solubility correlation 4.80 e130) HPLC 4.50 (0.15) Recommended CyyHyq —-Phenanthrene CAS # 85-018 *4.46 D124 SF 4.52 D 92 SE 4.57 DoS 25, SE AS w Both 4.28 I 87 HPLC 431 I 92 HPLC 4.50 I ug HPLC 4.63 I 42 head-space chromatographic method 107 4.64 I 33 25 from water solubility correlation Cyl, trans-1,2-Diphenylethene (trans-stilbene) CAS # 103-30-0 aural |e DE. 10d 4.81 (0.40) Recommended Cyglyy ‘I-Nethylfluorene CAS # 1730-37-6 s4a.o7f 38 4.97 I ug HPLC 4.97 (0-30) Recommended 4. Phys. Chem, Ret. Data, Vol. 18, No.3, 1980,OCTANOL-WATER PARTITION COFFFICIENTS OF SIMPIF ORGANIC COMPOUNDS = 1125 Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Method Log P Code Ref, Temp. + Method Method = Phase += Analyzed Ref. Cathe 9,10-Dihydroanthracene CAS # 613-31-0 425 Dnt 4.25 (0.30) Recomended Cathy Bibenzyl (1,2-diphenylethane) CAS # 103-29-7 “4.79 D104 ye ee 4.600 1 116 HPLC am 1 65 HPLC aiez oT a7 from solubility ratio 4.70 (0.20) Recommended Cygtyy 4,4" DimethyLbiphenyl CAs # 613-35-2 5.09 D 81 25 6 ac Ww Both = 129 5.09 (0.30) Recomended Cy4tpg -—«--Phenyloctane (n-octylbenzene) CAS # 2189-60-8 6.30 D 68 SF ac w Both 6.30 (0.40) Recommended Cys, -I-Nethylphenanthrene CAS # 832-69-9 tos |e 209 HPLC 5.08 (0.40) Recommended C\sHyp -2Methylphenanthrene CAS # 2531-84-2 5.24 1 119 WLC 5.24 (0.40) Recommended CysHhz -S-Methylphenanthrene GAS # 8652-71-53 5.151 ng HPI. 5.15 (0.40) Recommended 4 Phys. Chem, Ret. Data, Vol 18,No. 3, 19801136 JAMES SANGSTER Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Method log P Code Ref. Temp. Method Method Phase = Analyzed Ref. Cygth --S-Methylanthracene CAS # 779-02-2 5.07 D113 25 SF AS Ww Both 4.96 1 99 from solvatochronic parameters 5.07 I 38 25 from water solubility correlation 5.10 I ng HPLC 51651 33-25.‘ from water solubility correlation 5.07 (0.20) Recommended Cling Pyrene CAS # 129-00-0 ae S208 ee Dey iss os SF RC W Both 134,135 bad 1D a 103) a cs SF AS W Both 4.500 I 122 HPLC $08 I 119 HPLC 5.12 33 25. from water solubility correlation 5.22 1 42 head-space chromatographic method 107 5.00 (0.20) Recommended Cygtyg -«“Fluoranrnene GAS # 200-44-0 5.208 D136 405 I uy HPLC 5.22 38 25. from water solubility correlation 5.29 33-25. ‘from water solubility correlation 5.20 (0.20) Recommended CygHyg -—=«-2Rthylanthracene CAS # 52251~71-5 5.85 I 19 HPLC 5.85 (0.30) Recommended City -«9-10-Dimethylanthracene CAS # 781-43-1 5.25 1 38 25. from water solubility correlation 5.25 oT 33 25. from water solubility correlation 5.480 oT 99 from solvatochromic paraneters 509 T)19 HPLC 5.69 (0.40) Recommended J. Phys. Chem, Ret. Data, Vol 18, No.2, 1989OCTANOL WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS 1127 Table 5. Aromatics (continued) Bquil. Anal. Ag. Phases Method Log P Code Ref, Temp. + Method Method = Phase += Analyzed Ref. Cygllyg _ I-Phenyldecane (n-decylbenzene) CAS # 104~72~3 7.35 D 68 SF auc Ww Both 7.35 (0.40) Recommended Cyt, 1s2-Benzofluorene (benz(a)fiuorene) CAS # 258-84-6 5.32 I 38 25 from water solubility correlation 5.33 I 33-26 ‘from water solubility correlation 5.68 I ug HPLC 5.40 (0.40) Recommended C7), 2,3-Benzofluorene (benz(b)fluorene) CAS # 243-17-4 3.73 5 38 25 from water solubility correlation 8.77 Teeee119) HPLC 5.75 (0.40) Recommended Cjgth 9,10-Benzophenanthrene (triphenylene) CAS # 217-59-4 5.49 1 us HPLC 5.49 (0.50) Reconmended CygH,, 1,2-Benzanthracene (benz(a)anthracene) CAS ¥ 56-55-35 5.91 I 38 25 from water solubility correlation 6:10 I 33 25 from water solubility correlation 5.79 1 us HPLC 5.91 (0.40) Reconmanded Ciel, Naphthacene (benz(b)anthracene) CAS # 92-24-0 *5.90 Dus 25 SF AS Ww Both 5.48 I 99 from solvatochromic parameters 5.54 I 23 25 from water solubility correlation 5.76 me ety HPLC 5.90 I 38 25 from water solubility correlation 5.76 (0.30) Recommended ‘Phys. Chem. Ret Data, Vol. 18, No.3, 1980,1138 JAMES SANGSTER, Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Nethod Log P Code Ref. Temp. Method Method Phase © Analyzed Ref. Cygthp -«Chrysene CAS # 218-01-9 5.91 D 68 5.73 1 ug 5.791 38 25 6.01. 1 33-25. from water solubility correlation 5.86 (0.40) Recommended gly 4-Phenylbiphenyl (p-terphenyl) CAS # 26140-60-3, 6.03 oT 123, HPLC 6.03 (0.50) Recommended Cogya -—-Perylene CAS # 198-55-0 5.82 1g HPLC 650 eel 38 25 from water solubility correlation ess 1 33 25 from water solubility correlation 6.25 (0.50) Recommended Coglyy _-_-3,4-Benzopyrene (benz(a)pyrene) CAS # 50-32-8 600 De eis cs SF AS, w Both 6.50 D 68 SF GLC Ww Both %5.97, 1137 WLC 5.98f 38 25 from water solubility correlation cue uy HPLC 6.50 I 128 HPLC 657 1 3325. ‘from water solubility correlation ema 6 ic 6.83 oT 138 WIC 6.35 (0.40) Recommended Coglt,2 _-—«-3,4-Benzofluoranthene CAS # 205-99-2 3.78 1 us MLE 5.78 (0.50) Recommended Cooly 9-Phenylanthracene CAS # 602-55-1 6.01 oT ng HPLC 6.01 (0.50) Recommended 4.Phys. Chem. Ret. Data, Vol 18, No.3, 1989,OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS = 1130 Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Method Log P Code Ref. ‘Temp. Method Method Phase «Analyzed Ref. Coot _-7,12-Dimethylbenz(a)anthracene CAS # 57-97-6 “5.80 D133 ANB SE RC Ww Both 134 5.80 (0.50) Recommended Cote 3-Methylcholanthrene CAS # S6-49-S “6.02 133 ANB SF RC Ww Both 134 vce iT 33 25 Crum water sulubility wirelativw tem 38 25 from water solubility correlation 6.75 (0.50) Recommended Coot, _-—Benzo(g,h,i)perylene CAS # 191-24-2 ozs 1 yy trom solvatochromc parameters 6.63 I 1g HPLC 6.77 1 33 25 from water solubility correlation 710 oT 38 25 from water solubility correlation 6.90 (0.40) Recommended Contin 2,3:6,7-Dibenzanthracene (pentacene) aga 38 25 from water solubility correlation 7.19 (0.70) Recomended Coty 1,2:3,4-Dihenzanthracene (dihen2(a,c)anthracene) 7g) 38 25 from water solubility correlation 7.19 (0.70) Peconmended Coty 1,2:5,6-Dibenzanthracene (dibenz(a,h)anthracene CAS # 53-70-3 crs0| 133 ANB SF RC W Both 134 ered 99 from solvatochromic parameters mags 38 25° frum water Solubility correlation 6.75 (0.40) Recommended Coty 3,4-Benzonaphthacene (benz(a)naphthacene) CAS f 226-88-0 Orel 9 HPLC 6.81 (0.70) Recommended Phys. Chem. Ret Data, Vol 18, No. 3, 18691140 JAMES SANGSTER Table 5. Aromatics (continued) Equil. Anal. Aq. Phases Method Log P Code Ref. ‘Temp. Method Method Phase += Anallyzed Ref. ne # 191-07- Cyytyy Coronene CAS # 191-07-1 “5.4001 94 Uric 764 38 25 from water solubility correlation 6.5 (1.0) Recommended Phases were D20 and Cat 70D. » average value. © From a restricted correlation plot. 4 Extrapolated to zero concentration in organic phase. ©D. Koteias, personal communication £ It is not clear whether this is authors’ value or one from the Literature. 8 W. Klopffer et al., personal commmication. ‘.Phys. Chem. Ret. Data, Vo. 18, No.3, 1969,OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS saat Table 6. Cycloalkanes and cycloalkenes Equil, Anal. Aq. Phases Method log P Code Ref. Temp. Method Method Phase Analyzed Ref. Cstyg Cyclopentane CAS # 287-92-3 2.64 D 104 *3.00 104 2.057 I 42 hhead-space chromatographic method 107 3.00 (0.30) Recommended Coils -'1-3-Cvclohexadiene CAS # 592-57-4 Cy) Both 2.47 (0.75) Recemmended Cellg -‘Lsd-Cyclohexadiene CAS # 628-41-1 *2.30 0 D104 2.30 (0.25) Recommended Cellyg _Cyclohexene CAS # 110-83-8 1.907 D 139 © cic 1 +2186 104 Both 2.86 (0.25) Recommended CgHyy Cyclohexane CAS # 110-82-7 esraiee 0) 104 2.447 1 42 head-space chromatographic method 107 S70ee Tt 22 25 from measured activity coefficients 3.44 (0.35) Recommended Cglz _-Methyleyclopentane CAS F 96-37-7 3370 OD 104 2.382 «iT 42 head-space chromatographic method 107 3.37 (0.30) Recommended Cig 1,3,S-Cycloheptatriene CAS # S44-25-2 2065 eee 92 SF 3.03 92 HPLC 2.63 (0.40) Recommended ‘Phys, Chem. Ret Data, VoL 18, No.3, 19801142 JAMES SANGSTER Table 6. Cycloalkanes and cycloalkenes (continued) Equil. Anal. Aq. Phases Method Log P Code «Ref. Temp, Method Method = Phase «Analyzed ~ Ref. Cy,y —-Methylcyclohexane CAS # 108-87-2 2.767 a2 head-space chromatographic method 107 3.88 (0.40) Recommended Cyt. _-—«-1,5-Cyclooctadiene CAS # 111-78-4 3.16 D 92 SE 3134 T 92 HELE 3.55 (0.40) Recomended Cyt Cyclooctane CAS # 292-64-8 3.287 42 head-space chromatographic method 107 4.45 (0.40) Recommended Cyoly —-Adamantane CAS # 281-25-2, 5.202 D140 SF RC pHT.4 Both 1 4.24 (0-50) Recommendea Cyothg -1,5,9-Cyclododecatriene CAS # 4904-61-4 4.122 D 92,142 SF +65 rma HPLC. 5.50 (0.40) Recommended 4. Phys. Chem. Ret Data, Vol 18, No.3, 1989,OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS 1142 Table 7. Mixed-type hydrocarbons Equil. Anal. Ag. Phases Method Log P Code Ref. ‘Temp. + Method Method = Phase © Analyzed Ref. Calis Ethynylbenzene CAS # 536~74-3 eztes: 220) 20 SF as. Ww AQ 46, 2.16 I 143 HPLC 2.40 (0.25) Recommended Cyl, Phenylethene (styrene) CAS # 100-42-5 @rrocle |p 7 104) 3.16 =D 108 23 SF HPLC W Both 2.76 1 144 HPLC 2900 his HPLC 3.3900 4 25 from UNIFAC activity coefficients 3.05 (0-30) Recommended Coy 1-Phenyl-1-propene CAS # 637-50-3 us 104 3.35 (0.15) Recommended Cog 3-Phenyl-1-propene (allylbenzene) CAS # 300-57-2 3:2) 104 3.23 (0.15) Recommended Co Indane CAS # 496-11-7 3.18 D 104 ise D 104 3.33 (0.30) Recommended Cgtlg _Phenylcyclopropane (cyclopropylbenzene) CAS # 873-49-4 *3.27 D 104 3.27 (0.25) Recommended Cystho — Hept-1,3-diyn-S-enythenzene CAS # 13678-98-3 CE us HPLC 112,146 4.8 (1.0) Recommended J. Phys. Chem. Ret Data, Vol 18, No.3, 10801144 JAMES SANGSTER Table 7. Mixed-type hydrocarbons Equil. Anal. Aq. Phases Method Log P Code Ref. Temp. Method Method Phase © Analyzed Ref. Cyq,z _-Vimylacenaphthene (isoner not specified) 3.99 rT 119 ‘HPLC 3.99 (0.40) Recommended Table 8. Euler Equil. Anal. Aq. Phases Method Log P code Ket, Temp. Method Method = Phase Analyzed Ret. CyH,0 Epoxyethane (ethylene oxide) CAS # 75~21-8 0.50 =D 104 Both ~0.30 (0.20) Reconmended CHO Oxapropane (dimethyl ether) CAS # 115-10-6 *0.10 =D 104 Both 0.10 (0.20) Recommended C3H,0 1,2-Epoxypropane (propylene oxide) CAS # 75-56-9 *0.03 D104 0.03 (0.10) Reconmended Cyto 1,4-Epoxy-1,3-butadiene (furan) CAS # 110-00-9 1.34 D104 Both 134 D loa 113 I 13 HPLC 1.34 (0.20) Recommended CyHg0 _—-1,4-Epoxy-2-butene (2,5-dihydrofuran) CAS # 1708-29-8 0.46 D104 Both 0.46 (0.25) Recommended 41 Phys. Chem, Ret. Data, Vo. 18, No. 3, 1989COCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS 1145 Table 8. Ethers (continued) Equil. Anal. Aq. Phases Method log P Code Ref. ‘Temp. Method Method == Phase «Analyzed Ref. CyH,0 3-Oxa-1-pentene (ethylvinyl ether) CAS # 109-92-2 1.04 D108 1.04 (0.20) Recommended C40 _-—‘1,4-Hpoxybutane (tetrahydrofuran) CAS # 109-99-9 0,22 D 80 SF cuc W ORG 040 = D104 xoth 0.46 (0.10) Recommended CyHy,0 3-Oxapentane (diethyl ether) CAS # 60-29-7 0.77 D 104 0:83 0D 147 20 SF cR Ww Both 148 “0.89 104 Both 0.89 (0.10) Recommended CHO 2-Methylfuran CAS # $34-22-5 1.85 D104 1.85 (0.20) Recommended CgHjg0 _-1,5-Epoxypentane (tetrahydropyran) CAS # 142-68-7 0.64 80 SF cic W RG 0.82 (0.20) Recommended C,Hy,0 2-Oxa-3,3-dimethyIbutane (methyl t-butyl ether) CAS # 1634-04-4 70.94 80 SF cic W ORG 0.94 (0.30) Reconmended Clg 2-Fthylfirran cas # 3908-16-01 e740) |) 104 2.40 (0.20) Recommended Cg _-1,2-Epoxycyciohexane CAS # 286-16-8 1.26 oD 149 37 SF cue pT. ORG 1.30 (0.30) Recommended ‘Phys. Chem. Ret Data, Vol 3, 19001148 JAMES SANGSTER, Table 8. Ethers (continued) Equil. Anal. Aq. Phases Method Log P Code Ref. Temp. Method Method Phase Analyzed Ref. CHO _-—cis-2,5-Dimethyltetrahydrofuran CAS # 2144-41-4 “1.22 =D 80 SF GLC Ww ORG 1.22 (0.25) Recommended Cg,,0 _trans-2,5-Dimethyltetrahydrofuran CAS # 2390-94-5 1.34 Dao se aie w ora 1.34 (0.25) Recommended Cgti,yO 4-Uxaneptane (di-n-propyl ether) CAS # L11-43-5 "2.03 «D4 2.03 (0.15) Reconmended Cgiy40 -3-Oxa-2.4-dimethvlpentane (diisopropyl ether) CAS # 108-20-3 Siisca1 12 DE a 60 SF GE W ORs 1.52 (0.25) Recommended Cty S-Oxaheptane (butylethyl ether) CAS # 628-81-9 “2.03 Dl SF GC w one 46 2.03 (0.15) Reconmended CyH0 _-Methoxybenzene (anisole) CAS # 100-66-3 2.08 D405 sr ‘5 BIA Doth «17 Sbitgu ea) ci AG es cz) SF 4S Ww AQ 2.08 Gs eo 60 HPLC abies eee |e HPLC 2.24 I 97 HPLC 2.11 (0.10) Recommended CyH,0 -Benzofuran CAS # 271-89-6 “2.67 Dh 2.67 (0.20) Recommended 4: Phys. Chem Ret Data, VoL 18, No.3, 1989,OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS 1147 Table 8. Ethers (contimed) Equil, Anal. Ag. Phases Method log P Code Ref. ‘Temp. Method Method Phase ~ Analyzed Ref. Cyto Phenylepoxyethane (styrene oxide) CAS # 96-09-3 ‘1.51 0D 19 37 SF Gc pHT.A org ‘lel 0D 104 eter 151, SF HPLC NS Both 1,61 (0.20) Recommended Clg -—_-2,3-Dihydrobenzofuran CAS # 496-16-2 214 DSL SF HPLC Ns Both 2.14 (0.20) Recommended CylljO -‘Benzylmethyl ether CAS # 538-86-3 “1.35 D104 1.35 (0.15) Recommended Cyllyg® _‘Ethoxybenzene (phenetole) CAS # 103-73-1 *251 D 104 i 37 PLC 2.51 (0.20) Recommended CyHjg0 _-«2-Methylanisole CAS # 578-58-5 "2.74 D 104 2.74 (0.20) Recommended Gyltjg° -«S-Mothylanisole GAs # 100-845 2.66111 |) 104 2.66 (0.20) Reconmended Cylly,0 4-Methylanisole CAS # 104-93-8 2.66 oD 104 *2.81 9D 104 2.81 (0.25) Recommended Cyt, 0 1-Viny1-3,4-epoxycyclohexane 2.08 oD M9 37 SF GLC pHT.4 ORG 1.90 (0.20) Recommended ‘Phys. Chem. Ret. Data, Vol 18, No.3, 1989aan Table 8. Ethers (continued) Equil, Anal, Aq. Phases Method log P Code Ref, Temp, Method Method © Phase Analyzed Ref. Cyt 40 Cyclohexylepoxyethane 288 oD 1937 SF cic pH or 2.28 (0.20) Recomended Coty 5-Oxanonane (di-n-butyl ether) CAS # 142-96-1 3.21 D 15225 SF Guc Ww 3.21 (0.25) Recommended CoH 4-Oxa-2,6-dimethytheptane (diisopropyl ether) CAS # 628-SS-7 2.78 oD 80 SF ac Ww oRG 7.78 (0.25) Recommended Cgftyg0 -Allylphenyl ether CAS # 1746-13-0 “2.98 D104 2.94 (0.30) Recommended CgHy,0 _—-~Ethylbenzyl ether CAS # 539-30-0 2.16 z 131 2.16 (0.20) Recommended Cgli,,0 Phenylpropyl ether CAS # 622-85-5 73.18 D 104 3.18 (0.30) Recommended Cath, 0 2,6-Dimethylanisule AS # 1004-66-6 42.92 D 104 2.92 (0.30) Kecommended CyothyO —-A+Methoxy-3-phenylpropane CAS # 2046-33-5 *2.70 D 120 SF AS Ww AQ 46 2.70 (0.30) Recomended 4 Phys. Chom, Ret. Data, Vol. 18, No. 3, 1989OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE UHGANIC CUMPUUNDS = 1149 Table 8. Ethers (continued) Equil. Anal. Aq. Phases ‘Method Log P Code Ref. Temp. ‘Method Method Phase Analyzed Ref. Cy HO Dibenzofuran CAS # 132-64-9 “42 D108 47 «De SF HPLC Ww Both 3.96 rT 138 HPLC 4.12 (0.20) Recommended 71,90 Diphenyl ether CAS # 101-84-8 4.08 =D 108 23 SE HPLC W Both moo) a0 ass, mn. SF ce w Roth “4.20 104 4.36 104 3.870 Or 65 HPLC 4.21 (0.20) Recommended Cy gHt20 1, 2-Epoxycyclododecane 4.70 1 al HPLC 4,57 (0.35) Recommended C329 —-Renzylpheny1 ether CAS # 946-R0-5 3.79 D 104 3.79 (0.30) Recomended ® average value. 4. Phys. Chem, Ref, Dats, Vol. 18, No 3, 19691480 Table 9. Alcohols JAMES SANGSTER Equil. Anal. Age Phases Method Log P Code Ref. Temp. + Method +Method = Phase © Analyzed Ref. cH,0 Methanol CAS # 76-56-1 0.82 D 47 SF R w Both 148 “0.77 D104 Both “071 D 27 25 SF cue pH? Both 158 0.70 oD = 110 SF 0.68 D184 SF AS 0.662 D155 HO 052 D156 SF RC b Both -0'32 D487 3A SE BC pH. Both 0.642 153 -0.74 (0.07) Recommended C,H,0 “Ethanol CAS # 64-17-5 0.528 D155 SF HG -0.32 D147 20 SF R W Both 148 “0.31 oD 104 Both ey oth SF GLC Ww one 162 -0.50 160 25 SF RC W Both 0.22 =D 161 pH?.2 Botz0 | 0 27 28 SF uc pH? Both 158 “0.18 oD 156 SF RC b Both Dost SF AS 0.30 (0.03) Recommended C3H,0 2-Propyn-1-ol CAS # 107-19-7 0.38 =D 104 0.38 (0.20) Recommended CHO 2-Propen-1-ol (allyl alcohol) CAS # 107-18-6 uly Duh 0.17 (0.10) Recommended CHO 1-Propanol, CAS # 71-23-8 “0.25 oD 104 Both 0:30 oD 1s9 SF GLC Ww one 162,163 0.32 =D 27 25 SF GLC paT Both 158 0.25 (0.05) Recommended “4 Phys. Chem. Ret, Data, Vo. 18, No.3, 1989,OGTANOL-WATEH FAK! JON GUEPFIGIENIS UF SIMPLE UHGANIG GUMPOUNUS = 1151 Table 9. Alcohols (continued) Equil. Anal. Aq. Phases Method Log P Code Ref, Temp. + Method Method += Phase «Analyzed Ref. C3H,0 _2-Propanol. CAS # 67-63-0 02051) 0) 159 SF cic Ww one 162,163 0.141 164 HPLC 0.05 (0.20) Recommended Cyitjg0 «I~ Butanol CAS # 71-36-3 user Ayr ok as 0.79 D 9,10 25 G cue Ww Both = 1 0.79 =D 58 25 G Gc W Both 9 oe7 oD 27 25 SP cic pH? Both «158 “0.88 = D108 ieee | DE | 155 SF HG 0.89 =D 104 o:o5) | DE 156 SF RC b Both 0.76 0 «I 10 25 from measured activity coefficients 0.80 0 58 25 from measured activity coefficients 1020 165 HPLC 0.84 (0.04) Recommended Cyl -2-Methyl-1-propanol (isobutanol) CAS # 78-83-1 0.65 oD 104 0.7% =D 159 SF cuc Ww one 162,163 0.83 oD 1a7 20 SF R W Both =“ 148 0.76 (0.07) Recommended Cy? 2-Butanol CAS # 78-92-2 0.61 D lm SF cc Ww one 46 O81 I 165 HPLC 0.65 (0.10) Kecommendea ClO *0.35 D 0.37 D 0.39 I 0.59 I 0.35 (0.10) Recommended 104 m1 164 165 2-Methyl-2-propanol (t-butyl alcohol) GAS # 75-65-0 Both SF cic Ww one HPLC HPLC «4 Phys. Chem, Ret, Data, Vol 18, No.3, 19891162 JAMES GANGSTER Table 9. Alcohols (continued) Equil. Anal. Aq. Phases Method Log P Code Ref. Temp. + Method Method Phase += Analyzed Ref. CHO 2-Methy~3-butyn-2-o1 CAS # 115-19-5 70.28 D104 0.28 (0.10) Recommended Cgltjj0 —A-Pentanol CAS # 71-41-0 140 D104 i490 27 25 SE cc pT Both 158 153 58 25 G cc W Both 9 153 D910 25 G oie W Both =I “1:56 D104 Both 1.3301 122 HPLC 14g 165 HPLC iss 58 25 from measured activity coefficients 1.51 (0.05) Recommended Cel 0 $-Nethy1-1 butanol (isopentanol) CAS # 125-51-3, 1.16 D 104 14200 104 Both Teiguaely 164 HPLC 1.28 (0.12) Reconmended CeHl,0 2, 2-Dimethyl-1-propanol CAS # 75-84-3 132 D159 sk wu « one 162,165 1.36 -D (30,111 SF cue W one 46 ‘Lat or 164 HPLC 1.31 (0.05) Recommended Coiy0 Petar cas # 6032-23-7 1190-1 164 HPLC Va 168, Hpre, 1.25 (0.06) Recommended Catt 90 ‘S-Pentanol CAS F 98d-Ud-1 analy ae) 104 Both i 164 HPLC aisyget 165 HPLC 1.21 (0.10) RecommendedUGTANOL-WATER PARTITION GOEFFIGIENTS OF SIMPLE ORGANIC COMPOUNDS: 193 Table 9. Alcohols (continued) Equil. Anal. Ag. Phases Method Log P Code Ref. ‘Temp. Method Method Phase Analyzed Ref. CiH,0 - S-Methy1-2-butanol CAS # 598-75-4 “1.28 D 159 SF GLU Ww one 162,163 1.61 = 166 HPLC 1.28 (0.20) Recommended CgHy,0 --2+Nethyl-2-butanol CAS # 75-85-4 0.89 =D 105 SF 0.89 =D 30 25 SF ac OW AQ 46 0.89 (0.10) Recommended CyH,0 -«‘2+Ethyl-2-propanol (tert-pentanol) CAS # 75-84-4 2 0.89 D167 SF AS Ww AQ 46 1.15 Ti 165 HPLC 0.95 (0.10) Recommended Cetigo Phenol CAS # 108-95-2 0.602 =D 169 18 SE AS pli6.8 AQ 0.622 «=D «172 SF CR,AS_-—pH?.4 1Q 1 he SF CRAAS.- pH AQ ty = eee ey G WLC OW Both 146 oD 86 20 SE AS W Q 46 “146, DO 46 25 SE AS W AQ lst D168, SF 175 SARE Dee 20t 148 D8 22 AKUFVE 50 pase eth ee SF Ae plle.6 AQ este Di ete 25) SF RAS) ih AQ 154 DO 50 25° ANUFVE «AS. pH Both 1300 DO 8 SF AS NS AQ uss D160 SF CRASH AQ 173 DT SF AS ph ORG 1.08 I 75 25. rom INTRA activity enefficients ae = eee 120 HPLC 1.35, fn 6 HPLC 14ze 65 HPLC 1492170 ss?) (177 25 1.57 I 173 —«37_—microelectronetric titration 160?) (1768 W 178 lol (178 FPLC and thin-layer chromatography 2.20 2 153 1.50 (0.05) Recommended ‘4 Phys. Chem. Ret. Data, Vol 18, No.3, 19891154 JAMES SANGSTER, Table 9. Alcohols (continued) Equil. Anal. Ag. Phases Method log P Code Ref. ‘Temp. Method Method © Phase Analyzed Ref. Cathy 0 Cyclohexanol CAS # 108-93-0 ‘1.23 30,211 SF ou W one 46 1.25 (0.20) Recommended 1-Hexanol cas # 111-27-3 D4sz 25 SF cue W 2 Do Yu} 6 wut " som AL D104 D 58 25 G cic W Both 9 D 27 25 SF cc ph Both 158 I 122 HPLC I 165 HPLC I 164 UPLC I 58 25 from measured activity coefficients 2.03 (0.03) Recommended Coty 2Hexanol CAS # 626-93-7 “Lib 104 HPL 1.76 (0.20) Recommended Cay 3-Hexanol CAS # 623-37-0 16500 164 HPLC 1.65 (0.20) Recommended Cg 5,S-Wimechy1~2~uranol CAS # 4904-07-35, 148° =D so SF uc W one 162,165 1.48 (0.20) Recommended C7H,0 Benzyl alcohol CAS # 100-51-6 1.00 D179 20 SF AS NS AQ 110 D156 SE RC ’ Both Vio p04 “110 -D 30,4628 SE AS W AQ 0.872183, aos oT 65 HPLC 1.05 (0.10) Recommended Phys. Chem, Ret. Data, Vo. 18, No.3, 1989,OGTANOL-WATER PARTITION GOEFFIGIENTS OF SIMPLE ORGANIG GUMPUUNDS 1155 Table 9. Alcohols (continued) Equil. Anal. Aq. Phases Method log P Code Ref. Temp. Method Method Phase += Analyzed Ref. CHO 2-Methylphenol (o-cresol) CAS # 95-48-7 1.93 DI 221175) 37 SF PHT. *1.95 DE 104 1.96 D 10 25 G HPLC Ww Both 1197 Dp 10d) 2.01 D Ft 35 SF AS NS AQ 04 D180 22 SF CR,AS, £ AQ 1.93 roam HPLC and thin layer chromatography 2.09 Te 166 HPLC 1,98 (0.05) Recommended CoHi0 3-Methylphenol (m-cresol) CAS # 108-39-4 4 Doms SF par.d 19s¢ D168 SF 17s 19600 DO 46s SF aS Ww AQ nite) 2D) oo) | 2s 6 HPLc Ww Both 201 D104 206 =D oT 8S SF AS Ns AQ 1.98 1 am HPLC 201 0? lah 1,98 (0.08) Recommended CHO 4-Nethylphenol —(p-cresol) —CAS # 106-44-5 aol D387 SF par.d 1.92 D104 ‘14, D468 25 SF as Ww AQ rosé on 16R SE 17s 198 8D 1B 2 SE AS Both 50 199° Dim 25 SF AS pHS.6 AQ 210 oD 47 35 SF AS NS AQ 1.62 I 87 HPLC 1.73 I 75 25 from UNIFAC activity coefficients 1.97 I 166 HPLC 2.03 I im HPLC 2:10 2 47 25 2.17 2 181 1.97 (0.07) Recomended CH, 49 cis+2-Methylcyclohexanol AS # 7443-70-21 1.84 ee 164) HPLC 1.84 (0.10) Recommended ‘Phys. Chem, Ret, Dats, Vol. 18, No.3, 19801158 JAMES SANGSTER, Table 9. Alcohols (contimed) Equil, Anal. Aq. Phases Method Log P Code Ref. Temp. Method Method = Phase Analyzed Ref. Cj, _trans-2-Methylcyclohexanol CAS # 7445-52-9 *1.82 rT 164 HPLC 1.82 (0.10) Recommended C740 4-Nethylcyclohexanol CAS # 589-91-3 ‘1.79 D104 1.79 (0.15) Recommended Cpl 60 2. Teptanot AS #121 70 6 2.87 D910 25 G cuc W Both 2.87 D 58 25 G ce W Both 9 2.60 D164 25 G cue W Both u 2.65 D2 25 SF GLC 8 pHT=— Both «158 +2.72 D104 2.39 I 12 HPLC 2.41 I 165 HPLC 2.62 (0.10) Recommended CH, ,0 2-Heptanol CAS # 543-49-7 *2.31 D104 2.31 (0.20) Recommended Ciyg0 -S-+Heptanol CAS # 589-82-2 a D104 2.24 (0.20) Recommended Cyt, 4-Heptanol CAS # 589-55-9 *2,22 D108 23 T 164 HPLC 2.22 (0.10) Recommended CgHyg0 _-«-3-Methylbenzyl alcohol CAS # 587-03-1 1.60 nD 4 5 SF AS w AQ 1.60 (0.15) Recommended 4 Phys. Chem. Re. Data, Vol 18, No.3, 188LUGIANUL-WAIEH PAHIITION GOEFFIGIENTS OF SIMPLE ORGANIC COMPOUNDS 1197 Table 9. Alcohols (contimued) Equil, Anal. Aq. Phases Method log P Code Ref, + Temp. + Method «Method += Phase «= Analyzed Ref. Cully 4-Nethylbenzyl alcohol CAS # 589-18-4 ‘1.50 D 46 25 SF As. w AQ ns8) 2 22D 108 1,58 (0.15) Recommended Clty 0 2-Bthylphenol CAS # 90-00-6 Lar kU 2.64 2 asi 2640 «iT 174 HPLC 2,47 (0.15) Recommended gt 90 S-LthyIphenol GAS F 620-17-7 2.40 OD 46 25 SF as W AQ 2470 181 259 1 HPLC 2,50 (0.10) Recommended Cty? 4-Ethylphenol CAS # 123-07-9 72.98 DAL 2 SF AS piis.6 AQ 2.60 D Vv 3500S. AS NS AQ 2.2 2 170 237 «1 14 HPLC 259? a7 25 2,50 (0,10) Recommended Clty 1-Phenylethanol CAS # 1517-69-7 “142 D104 1.42 (0.15) Recommended Cet, 0 2-Phenylethanol CAS # 60-12-8 a0 ee Dea! 270 20 SE As NS. 4Q 1.36 D120 SF aS Ww AQ 46 1.36 (0.10) Recommended1160 JAMES GANGETER Table 9. Alcohols (continued) Equil. Anal. Ag. Phases Method log P Code Ref, Temp. Method Method Phase Analyzed Ref. CF? 2,4-Dimethylphenol CAS # 105~67-9 "2.30 «D182 20 SF CRAS_ pH Qs 234 10 25 G Hic |W Bot avao | | De 108 23 SF RC W Both 2.54 D 7 35 SF AS NS AQ 2.35 (0.15) Recomended Ca, 0 2,S-DimethyTphennl CAS # Q5-R7=4 12.33 =D 182 20 SF CR,AS_— pa AQ 183 2.35 D 10 25 6 PLC! ew) Both 2.34 (0.15) Recommended gH g° 2,6-Dimethylphonol CAS. # 576 261 acon ed) | 1104 2.31 D 10 25 6 HPLC W Both "215600 D104 2.40 9D 17 35 SF AS pH AQ 2.07 I 57 HPLC 2:38 I 166 HPLC 2.36 (0.10) Recommended Cyl 0 3,4-Dimethylphenol CAS # 95~65-8 42,23 D 182 20 SF CR,AS pH? AQ 193 2,23 (0.25) Recommended CyH 0 3,5-Dimethylphenol CAS # 108-68-9 2.55 D104 235 a7 38 SF AS ONS AQ 2310? 170 2.381 75 25 from UNIFAC activity coefficients 2.35 (0.15) Recommended Cy 6° @, @,0:-2,6-Dimethylcyclohexanol CAS # 39170-84-8 *2.37 I 164 HPLC 2.37 (0.25) Recommended «4 Phys. chem, Ret, Data, Vol. 18, No.3, 1980‘OGTANOL-WATER PARTITION GOEFFIGIENTS OF SIMPLE ORGANIG COMPOUNDS 1159 Table 9. Alcohols (continued) Equil. Anal. Ag. Phases Method Log P Code Ref. Temp. Method Method Phase + Analyzed Ref. Cy gO ©, ot, B-2,6-Dimethylcyclohexanol CAS # 39170-83-7 2000 «I 164 HDLC 2.10 (0.25) Recommended Cyiyg0 a8 »B~2,6-Dimethylcyclohexanol CAS # 42846-29-7 “2.38 1 164 HPLC 2.38 (0.25) Recommended CyHyy? 1-Oetanal, cas # 121-87-5 cD 25 Of W AQ 8 3.16 D184 3 SE W on 3.27, a7 25 SF GLC. pH? Bo 158 2.80 1 165 HPLC 292 «Tan HPLC “2197 12 HPLC 3.07 (0.10) Reconmended Cyt, 2-Octanol CAS # 123-96-6 "2.90 1 164 HPLC 2.90 (0.25) Recommended Cyt g® 4-Uctanol CAS # 589-62-8 2.68 I 164 HPLC 2.68 (0.25) Recommended CoP? 3-Phenyl-2-propen-I-ol (cinnamyl alcohol) CAS # 1n4-S4-1 1.95 D 10d 1.7 OT 37 HPLC 1.95 (0.20) Recommended Cah 2° 3-Phenyl-1-propanol cAS # 122-97-4 185 D179 20 SF AS NS AQ 188 0 D120 SF AS W 40 46 1.88 (0.10) Recommended «4 Phys. Chem. Re. Data, Vol. 18, No.3, 19891160 JAMES GANGSTER Table 9. Alcohols (continued) Equil. Anal. Ag. Phases Method Log P Code Ref. Temp. + Method Method = Phase-« Analyzed Ref. Co 0 2-n-Propylphenol CAS # 644-35-9 *2,93 D108 2.93 (0.25) Recommended gH 20 4-n-Propyiphenol CAS # 645-56-7 *3.20 D W 35, SF AS NS AQ 324 ht 277) 25 3.20 (0.10) Recommended Cot 0 2-Isopropylphenol CAS # 88-69-7 *2.88 D104 2.88 (0.20) Recommended CoH, 20 2,3,6-TrimethyTphenot CAS # 7416-94-6 2.67 D 10 25 G HPLC Ww Both 2.67 (0-35) Recommended Gof, 0 2,4,6-Trimethylphenol CAS # 527-60-6 275 dD 10 25 Gi Htc) Ww Both 2.73 (0.35) Recommended Cty 1-Nonanol CAS # 143-08-8 due gtd ty 6 cue W yon LL “4.2600 «D108 4.02 (0.30) Recommended Cy gH0 1-Naphthol CAS # 90-15-3 2.31 Dee 165) 20 SF CR,AS. £ *2.84 D172) SF FL puT.4 1 2.98 D1 SF AS W 46 3.09 D186 SF g pHO.5 AQ 2.28 I 57 HPLC 2.84 (0.20) Recommended 4 Phys. Chem Ret. Data, Vo. 18, No.3, 1980(UCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS = 1161 Table 9. Alcohols (continued) Equil. Anal, Aq. Phases Method Log P Code Ref, Temp. Method Method Phase += Analyzed Ref. C0 2-Naphthol CAS # 155-19-3, “2.70 D187 SF as. £ Both 46 28400 «Do SF 4S W one 46 2.89 D185 20 SF RAS £ AQ 2.408 65 HPLC 2.70 (0.15) Recommended CaF 4-n-Butylphenol CAS # 1638-22-8 365 oD W 20 SF AS Ns 40 3.65 (0.20) Recommended Cyotya? S-LereButyIpleusl GAS H-96-54-4 3.00 p 110 SF 3.04 (0.40) Recommended Cok cis-d-tert-Butylcyclohexanol CAS # 937-05-3 3.02 «I (168 HPLC 3.02 (0.40) Recommended Cag? trans-4-tert-Butylcyclohexanol CAS # 21862-63-5 *3.09 Te los HPLC 3.09 (0.40) Recomended Cy gH 1-Decanol CAS # 112-30-1 4.57 D104 3.98 ap i22 HPLC 4.57 (0.50) Recommended Cy pHlyg0 1-Dodecanol CAS # 112-53-8 *5.13 D 104 5.24 De 32 SE auc PHT Both 5.04 iy e27) HPLC 5.13 (0.30) Recommended «4 Phys. Chem, Ret, Dats, Vol. 18, No.3, 19601102 JAMES SANGSTER Table 9. Alcohols (continued) Equil. Anal. Aq. Phases Method Log P Code Ref. ‘Temp. Method Method Phase Analyzed —Ref. ©, 3400 ‘7-Phenyl-4,6-diyn-hept-2-en-1-ol CAS # 13641-62-8 2.48 1 us HPLC 2.48 (0-50) Recommended 3H, 0 Diphenylmethanol CAS # 91-01-0 2.03 =D 104 sete 1D) et acs) SF 1 2.67 Da 2.67 (0.25) Recommended CyqHgO _-Phenyl~2-methylphenyimethanol CAS # 5472-13-9 3.06 DO 10t 3.06 (0.30) Recommended Cyglyq® -Phenyl~4-methylphenylmethanol CAS # 1517~63-1 +3.13 D104 3.15 (0.30) Recommended C820 2,6-Di-sec-butylphenol CAS # 5510-99-6 4.38 1 108 HPLC 4.4 (1.0) Recommended CyHyg ——Trinhenytmethannt CAS # THeRA-6 13.68 D104 3.68 (0.40) Recommended J. Y. Park, unpublished data. ° Schistosome saline solution. © D, Kotzias, personal commmication. 4k. thomae, personal commmication. © From a restricted correlation plot. f spcidifieg". ® Chemical reaction followed by density measurement. } average value. 4. Phys. Chem. Ret. Data, Vol 18, No.3, 1989OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS ‘1163 Table 10. Aldehydes Equil, Anal. Aq. Phases Method log P Code Ref, + Temp. +‘ Method «Method = Phase «= Analyzed Ref. a0 Nethanal (formaldehyde) CAS # 50-00-0 0.35 iss 25, SF cR w Both 0.35 (0.10) Recommended CyH,0 Ethanal (acetaldehyde) CAS # 75-07-0 0.52 D 10 25 iG) jie w Both 0.45 (0.10) Recommended oyH0 Propenal (aerelein) cas # 107-02-8 0.01 D104 ~0.01 (0.25) Recommended HH, Propanal CAS # 123-38-6 0.59 D104 0,59 (0.20) Recommended CyHi,0 Butanal CAS # 123-72-8 “0.88 =D 104 0.88 (0.20) Recomended CHO 2-Ethylpropenal CAS F 922-63-4 “1.24 D104 1,24 (0.20) Recommended Cgtyy0—Texanal CAS # 0625-1 i) 189 25 SF auc aT AQ 46 1.78 (0.15) Recommended ‘.Phys. Chem. Ref Data, Vol 18, No.3, 1989,1164 JAMES SANGSTER Table 10, Aldehydes (continued) Equil. Anal, Aq. Phases Method Log P Code Ref. ‘Temp. Method Method Phase «Analyzed Ref. CHigo Benzaldehyde CAS # 100-52-7 143° D190 25 SF AS w orc 191 145) -D IL 25 SF AS pH5.6 AQ 1480 «D108 148 64 HPLC 1.560 «1 65 PLC 2.33 «1 56 HPLC 1.48 (0.08) Reconmenaea CHO Phenylethanal CAS # 122-78-1 “1.78 =D 104 1.78 (0.25) Recommended CgHlg0 2-Methylbenzaldehyde CAS # 529-204 *2.2 oD 192 AB SF AS W AQ 2.26 (0.20) Recommended CysH0 -—-7-PhenyThept-2-ene-4,6-diynal CAS # 20252-42-0 3.09 4s HPLC 112,146 3.1 (2.0) Recommended average value. «4. Phys. Chem. Ref. Data, VoL 18, No. 3, 1989OCTANOL WATER PARTITION COEFFICIENTE OF GIMPLE ORGANIC COMPOUNDE 1165 Table 11. Ketones Equil. Anal. Ag. Phases Method Code Ref. Temp. Method Method Phase Analyzed Ref. 2-Propanone (acetone) CAS # 67-64-1 D193 se ac w Q isa D u7 20 SF ck W Both 148 (0.10) Recommended Cylig0 2-Butanone (nethylethyl Ketone) CAS # 78-93-3 Oe et) or oR w Do 148 0.26 «=D 193 SF auc Ww AQ 194 *0.29 D-30,111 SF AS,GLC WW one 46 aso nina m0 0.697 =D 9,10 25 G GL f Both n 0.29 (0.05) Recommended 2-Pentanone cas # 107-87-9 D193 SE ac ¥ 2g 104 D «189s SF aS pHT nQ 46 (0.08) Recomended CH 0 3-Pentanone (diethyl ketone) CAS # 96-22-0 0.99 «=D 91025 6 ou Ww Both u 0.67 1 22 25 _— ‘from measured activity coefficients 0.75 I 10 25 _—‘from measured activity coefficients 0.82 (0.15) Recommended CoH? S-Mothy1-2-butanone CAS 8 565-20-4 40.56 D193 SF cur Ww AQ 194 0.56 (0.10) Recommended CligO I-Hexyn-5-one CAS # 2550-28-9 *0.58 D104 0.58 (0.15) Recommended CeO 2-Cyclohexene~1-one CAS # 930-68-7 0.61 bp 404 0.61 (0.15) Recommended ys. Chem, Ref, Dats, Vol. 18, No.3, 19801168 JAMES SANGSTER Table 11. Ketones (continued) Method Equil. Anal. Ag. Phases Log P Code Ref, Temp, Method Method Phase = Analyzed Ref. Cathy? I+Hiexen-5-one CAS # 109-49-9 ‘102 D120 SF 4S Ww AQ 1.02 (0.10) Reconmended Cellyg? cyclohexanone CAS # 108-94-1 “0.81 9D 104 0.81 (0.15) Recommended CHly20 2-Hexanone CAS # 591-78-6 119° D193 SF Gc Ww 4Q “1380 «D120 SF ‘AS W RQ 1.390 37 HPLc 1.38 (0.20) Recommended Getty 0 4-Methy1-2-pentanone CAS # 108-10-1 “isl D193 or ce w 4Q 1.31 (0.20) Recomended CH 40 2-Heptanone CAS # 110-43-0 “1.98 oD 9,10 25 G HPLC Ww Both zs p85 x ae W 2Q 2.08 «1 10 25 from measured activity coefficients 1.98 (0.15) Recommended CH 40 S-Methy1-2-hexanone cas # 110-12-3 lees 1D) 193 SF GLC Ww AQ 1.88 (0.15) Recommended 4. Phys. Chem. Ret. Data, Vol 18, No.3, 1980, 46 194 46 104 1 194 194OCTANOL-WATER PARTITION COEFFICIENTS OF SIMPLE ORGANIC COMPOUNDS: s407 lable 11. Ketones (continued) Equil. Anal. Aq. Phases Method log P Code Ref. ‘Temp. Method “Method = Phase~—«Analyzed Ref. gHg0 Acetophenone CAS # 98-86-2 ‘1g8 oD me SF AS w AQ ss D883 SF HPLC W Both so D197 AB SF RC Ww Both 163 92 SF 168 = =D 1905 SF AS W ons SL my att SF AS W AQ 46 158 1 196 WLC eso) 2 | i198 ares tT 92 HPLC 172 1 64 HPLC mA 63 HPLC vg0 0 TW HPLC 1.63 (0.05) Recommended Cal 0 2-Octanone CAS # 111-15-7 "2.37 D193 SF Guc w AQ 194 2.76 oD 9,10 25 G HPLC Ww Both Br 2.37 (0.10) Recommended Cfo Acrylophenone CAS # 768-03-6 eias) sen 10 1.88 (0.30) Recomended Colt, 0 Propiophenone CAS # 93-55-0 2.19 Dao au 0 | 190 25 SF AS W ons 191 216 37 HPLC 2.19 (0.10) Recommended Cyl, 00 4-Methylacetophenone CAS # 122-00-9 2.28 D195 SF 4S Ww AQ 46 ru) ft 196 HPLC 2.19 (0.10) Recommended 4. Phys. Chem, Ref, Data, Vol. 18,No 3, 19801168 JAMES SANGSTER, Table 11. Ketones (continued) Equil. Anal. Aq. Phases "Method Log P Code Ref, Temp. + Method Method = Phase Analyzed Ref. Caf g® 1-Pheny1~2-propanone CAS # 103-79-7 144 DO 120 SF AS Ww AQ 46 ety 64 HPLC 1.44 (0.10) Recommended Coty gO 2-Nonanone CAS # 821-55-6 x14 pags fl Ww AQ 194 3.18 oD 910 25 G HPLC W Both = 11 3.16 (0.20) Recommended Coy 0 S-Methyl-2-octanone CAS # 58654-67-4 292 D 193 SF ae w AQ 14 2,92 (0.20) Recommended CH, 4-Phenyl~3-buten-2-one (methylstyryl ketone) CAS # 122-57-6 *2.07 2 199 2,07 (0.30) Recommended C4 flag 2-Decanone CAS F 693-54-9 3.73 D 193 SF GLC W AQ 194 3.81 oD 910-25 G HPLC W bth i 3.77 (0.40) Recommended yh y0 4-Isopropyiacetophenone CAS # 045-15-0 2.98 I 196 thin-layer chromatography 2,98 (0.50) Recommended CyyH,,0 2-Undecanone CAS # 112+12-9 4.09 D193 SF cc W AQ 194 4,09 (0.30) Recommended CoH? 1-Acetylazulene CAS # 7206-57-7 2.87 oD aT SF AS Ww ORG 3 2.87 (0.25) Recommended 41 Phys. Chom. Ret. Data, Vol. 18, No. 3, 1089OCTANOL-WATER PARTITION COEFFICIENTE OF CIMPLE ONGANIO COMPOUNDS 1108 ‘able 11. Ketones (continued) Equil. Anal. Aq. Phases Method log P Code Ref. Temp. Method Method = Phase «Analyzed Ref. (2th 4-Phenylcyclohexanone CAS # 4894-75-1 230 «1 143, PLC 2.45 (0.25) Recommended gHyy0 Cyclododecanone CAS # 830-13-7 4101 14 HPLC 4.10 (0.40) Recommended ©5380 O-Fluorenone CAB # 486 25 9 “3.58 D 104 3.50 (0.30) Recommended Cyt 00 Benzophenone cAS # 119-61-9 3.12 D 104 3.18 0D 104 358 0D 190 25 SF AS. w ors 191, 3.18 (0.20) Reconmended Cy gthy2® 2-Phenylacetophenone CAS # 451-40-1 3.18 0D 104 3.18 (0.25) Recommended ® average veluc. Phys. Chom. Ret Data, Vol. 18, No.3, 19091170 JAMES SANGSTER Table 12. Acids Equil. Anal. Aq. Phases Method Log P Code Ref. Temp. Method Method Phase Analyzed Ref. G10, Methanoic (formic) acid CAS # 64-18-6 pK, = 3.74 “0.56 D 147 20 SF T w Both 148 -0.54 200 25 SF T Ww Both -0.54 (0.20) Recommended CyH,0, Ethanoic (acetic) acid CAS # 6419-7 pk, = 4.76 03 oD uy 20 SF r w Both as 0.30 D 201 28 SE T Ww Both -0.29 202 25 SF RC pal “0.17 D 104 0.2482 173 37 -0.17 (0.20) Recommended CHO. Propanoic acid CAS # 79-09-4 pK,= 4.87 (Ores aD 147 20 oF Y a oth 148 (0827/4 0} 203 SF T W AQ 204 70.330 104 Uesced Y as 37 0.33 (0.10) Recommended C4lig0. 2-Butenoic (crotonic) acid (isomer not specified) CAS # 3724-65-0 e0r72) a Die ot Pe altece 072 D108 0.664 2 173 0.72 (0.45) xecommended C,H,0, 2-Methylpropenoic (methacrylic) acid CAS # 79-41-4 pK, = 4.66 ores) Die cos) 2 SF T W Q 0.93 (0.20) Reconmended Cyg0, -«Butanoic acid CAS # 107-92-6 pK, = 4.82 0.79) Dy ea a7 220) SE T w Both 148 0838 20 337 oR 7206 0.79 (0.10) Recommended 4 Phys, Chem, Ret. Data, Vol. 18, No.3, 1989,