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Thiol
In organic chemistry , a thiol (/ˈθaɪɔːl/, /ˈθaɪɒl/)[1] is an organosulfur compound that
contains a carbon-bonded sulfhy dry l (R–SH) group (where R represents an alky l or other
organic substituent). Thiols are the sulfur analogue of alcohols (that is, sulfur takes the
place of oxy gen in the hy droxy l group of an alcohol), and the word is a portmanteau of
"thion" + "alcohol," with the first word deriv ing from Greek θεῖον (theion) = "sulfur". [2] The –
Thiol with a blue-
SH functional group itself is referred to as either a thiol group or a sulfhydryl group.
highlighted
sulfhydryl group.
Many thiols hav e strong odors resembling that of garlic or rotten eggs. Thiols are used as
odorants to assist in the detection of natural gas (which in pure form is odorless), and the
"smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as
mercaptans. [3][4] The term m ercaptan /mərˈkæptæn/ [5] was introduced in 1832 by William Christopher Zeise and
is deriv ed from the Latin mercurium captāns (capturing mercury )[6] because the thiolate group bonds v ery strongly
with mercury compounds. [7]

Contents
Structure and bonding
Nomenclature
Physical properties
Odor
Boiling points and solubility
Bonding
Characterization
Preparation
Laboratory methods
Reactions
S-alkylation
S-arylation
Acidity
Redox
Metal ion complexation
Thioxanthates
Thiyl radicals
Biological importance
Cysteine and cystine
Cofactors
In skunks
Examples of thiols
See also

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Footnotes
References
External links

Structure and bonding


Thiols and alcohols hav e similar connectiv ity . Because sulfur is a larger element than oxy gen, the C–S bond lengths,
ty pically around 180 picometers in length, is about 40 picometers longer than a ty pical C–O bond. The C–S–H angles
approach 90° whereas the angle for the C-O-H group is more obtuse. In the solid or liquids, the hy drogen-bonding
between indiv idual thiol groups is weak, the main cohesiv e force being v an der Waals interactions between the
highly polarizable div alent sulfur centers.

The S-H bond is much weaker than the O-H bond as reflected in their respectiv e bond dissociation energy (BDE). For
CH3 S-H, the BDE is 366 kj/mol, while for CH3 O-H, the BDE is 440 kj/mol. [8]

Due to the small difference in the electronegativ ity of sulfur and hy drogen, an S–H bond is polar. In contrast, O-H
bonds in hy droxy l groups are more polar. Thiols hav e a lower dipole moment relativ e to the corresponding alcohol.

Nomenclature
There are sev eral way s to name the alky lthiols:

The suffix -thiol is added to the name of the alkane. This method is nearly identical to naming an alcohol and is used by
the IUPAC. Example: CH3SH would be methanethiol.
The word mercaptan replaces alcohol in the name of the equivalent alcohol compound. Example: CH3SH would be
methyl mercaptan, just as CH3OH is called methyl alcohol.
The term sulfanyl or mercapto is used as a prefix. Example: mercaptopurine.

Physical properties

Odor
Many thiols hav e strong odors resembling that of garlic. The odors of thiols, particularly those of low molecular
weight, are often strong and repulsiv e. The spray of skunks consists mainly of low-molecular-weight thiols and
deriv ativ es. [9][10][11][12][13] These compounds are detectable by the human nose at concentrations of only 10 parts
per billion. [14] Human sweat contains (R)/(S)-3-methy l-3-sulfany lhexan-1-ol (MSH), detectable at 2 parts per billion
and hav ing a fruity , onion-like odor. (Methy lthio)methanethiol (MeSCH2 SH; MTMT) is a strong-smelling v olatile
thiol, also detectable at parts per billion lev els, found in male mouse urine. Lawrence C. Katz and co-workers showed
that MTMT functioned as a semiochemical, activ ating certain mouse olfactory sensory neurons, attracting female
mice. [15] Copper has been shown to be required by a specific mouse olfactory receptor, MOR244-3, which is highly
responsiv e to MTMT as well as to v arious other thiols and related compounds. [16] A human olfactory receptor,
OR2T11, has been identified which, in the presence of copper, is highly responsiv e to the gas odorants (see below)
ethanethiol and t-buty l mercaptan as well as other low molecular weight thiols, including ally l mercaptan found in
human garlic breath, and the strong-smelling cy clic sulfide thietane. [17]

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Thiols are also responsible for a class of wine faults caused by an unintended reaction between sulfur and y east and
the "skunky " odor of beer that has been exposed to ultrav iolet light.

Not all thiols hav e unpleasant odors. For example, furan-2-y lmethanethiol contributes to the aroma of roasted
coffee, whereas grapefruit mercaptan, a monoterpenoid thiol, is responsible for the characteristic scent of
grapefruit. The effect of the latter compound is present only at low concentrations. The pure mercaptan has an
unpleasant odor.

Natural gas distributors were required to add thiols, originally ethanethiol, to natural gas (which is naturally
odorless) after the deadly New London School explosion in New London, Texas, in 1937 . Many gas distributors were
odorizing gas prior to this ev ent. Most gas odorants utilized currently contain mixtures of mercaptans and sulfides,
with t-buty l mercaptan as the main odor constituent in natural gas and ethanethiol in liquefied petroleum gas (LPG,
propane). [18] In situations where thiols are used in commercial industry , such as liquid petroleum gas tankers and
bulk handling sy stems, an oxidizing cataly st is used to destroy the odor. A copper-based oxidation cataly st
neutralizes the v olatile thiols and transforms them into inert products.

Boiling points and solubility


Thiols show little association by hy drogen bonding, both with water molecules and among themselv es. Hence, they
hav e lower boiling points and are less soluble in water and other polar solv ents than alcohols of similar molecular
weight. For this reason also, thiols and corresponding thioether functional group isomers hav e similar solubility
characteristics and boiling points, whereas the same is not true of alcohols and their corresponding isomeric ethers.

Bonding
The S-H bond in thiols is weak compared to the O-H bond in alcohols. For CH3 X-H, the bond enthalpies are 365.7
(+/-2.1) for X = S and 440.2 (+/-3) kcal/mol for X = O. [19]

Characterization
Volatile thiols are easily and almost unerringly detected by their distinctiv e odor. S-specific analy zers for gas
chromatographs are useful. Spectroscopic indicators are the D2 O-exchangeable SH signal in the 1 H NMR spectrum
(33 S is NMR-activ e but signals for div alent sulfur are v ery broad and of little utility [20]). The ν SH band appears near
2400 cm−1 in the IR spectrum. [3] In the nitroprusside reaction, free thiol groups react with sodium nitroprusside
and ammonium hy droxide to giv e a red colour.

Preparation
In industry , methanethiol is prepared by the reaction of hy drogen sulfide with methanol. This method is employ ed
for the industrial sy nthesis of methanethiol:

CH3OH + H2S → CH3SH + H2O

Such reactions are conducted in the presence of acidic cataly sts. The other principal route to thiols inv olv es the
addition of hy drogen sulfide to alkenes. Such reactions are usually conducted in the presence of an acid cataly st or
UV light. Halide displacement, using the suitable organic halide and sodium hy drogen sulfide has also been
utilized. [21]

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Another method entails the alky lation of sodium hy drosulfide.

RX + NaSH → RSH + NaX (X = Cl, Br, I)

This method is used for the production of thiogly colic acid from chloroacetic acid.

Laboratory methods
In general, on the ty pical laboratory scale, the direct reaction of a halogenoalkane with sodium hy drosulfide is
inefficient owing to the competing formation of thioethers Instead, alky l halides are conv erted to thiols v ia a S-
alky lation of thiourea. This multistep, one-pot process proceeds v ia the intermediacy of the isothiouronium salt,
which is hy droly zed in a separate step:[22]

CH3CH2Br + SC(NH2)2 → [CH3CH2SC(NH2)2]Br


[CH3CH2SC(NH2)2]Br + NaOH → CH3CH2SH + OC(NH2)2 + NaBr

The thiourea route works well with primary halides, especially activ ated ones. Secondary and tertiary thiols are less
easily prepared. Secondary thiols can be prepared from the ketone v ia the corresponding dithioketals. [23] A related
two-step process inv olv es alky lation of thiosulfate to giv e the thiosulfonate ("Bunte salt"), followed by hy droly sis.
The method is illustrated by one sy nthesis of thiogly colic acid:

ClCH2CO2H + Na2S2O3 → Na[O3S2CH2CO2H] + NaCl

Na[O3S2CH2CO2H] + H2O → HSCH2CO2H + NaHSO4

Organolithium compounds and Grignard reagents react with sulfur to giv e the thiolates, which are readily
hy droly zed:[24]

RLi + S → RSLi
RSLi + HCl → RSH + LiCl

Phenols can be conv erted to the thiophenols v ia rearrangement of their O-ary l dialky lthiocarbamates. [25]

Many thiols are prepared by reductiv e dealky lation of thioethers, especially benzy l deriv ativ es and thioacetals. [26]

Reactions
Akin to the chemistry of alcohols, thiols form thioethers, thioacetals, and thioesters, which are analogous to ethers,
acetals, and esters respectiv ely . Thiols and alcohols are also v ery different in their reactiv ity , thiols being more
easily oxidized than alcohols. Thiolates are more potent nucleophiles than the corresponding alkoxides.

S-alkylation
Thiols, or more specific their conjugate bases, are readily alky lated to giv e thioethers:

RSH + R′Br + B → RSR′ + [HB]Br (B = base)

S-arylation

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Thiophenols are produced by S-ary lation or the replacement of diazonium leav ing group with sulfhy dry l anion
(SH− ):

ArN2+ + SH− → ArSH,[27][28]

Acidity
Relativ e to the alcohols, thiols are more acidic. The conjugate base of a thiol is called a thiolate. Butanethiol has a
pKa of 10.5 v s 15 for butanol. Thiophenol has a pKa of 6 v s 10 for phenol. A highly acidic thiol is
pentafluorothiophenol (C6 F5 SH) with a pKa of 2.68. Thus, thiolates can be obtained from thiols by treatment with
alkali metal hy droxides.

Redox
Thiols, especially in the presence of base, are
readily oxidized by reagents such as iodine to
giv e an organic disulfide (R–S–S–R).
Synthesis of thiophenolate from thiophenol
2 R–SH + Br2 → R–S–S–R +
2 HBr

Oxidation by more powerful reagents such as sodium hy pochlorite or hy drogen peroxide can also y ield sulfonic
acids (RSO3 H).

R–SH + 3 H2O2 → RSO3H + 3 H2O

Oxidation can also be effected by oxy gen in the presence of cataly sts:[29]

2 R–SH + 1⁄2 O2 → RS–SR + H2O

Thiols participate in thiol-disulfide exchange:

RS–SR + 2 R′SH → 2 RSH + R′S–SR′

This reaction is important in nature.

Metal ion complexation


With metal ions, thiolates behav e as ligands to form transition metal thiolate complexes. The term mercaptan is
deriv ed from the Latin mercurium captans (capturing mercury )[6] because the thiolate group bonds so strongly with
mercury compounds. According to hard/soft acid/base (HSAB) theory , sulfur is a relativ ely soft (polarizable) atom.
This explains the tendency of thiols to bind to soft elements/ions such as mercury , lead, or cadmium. The stability of
metal thiolates parallels that of the corresponding sulfide minerals.

Thioxanthates

Thiolates react with carbon disulfide to giv e thioxanthate (RSCS2 ).

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Thiyl radicals
Free radicals deriv ed from mercaptans, called
thiy l or thiol radical or mercapto radical, are
commonly inv oked to explain reactions in
organic chemistry and biochemistry . They
hav e the formula RS• where R is an organic
substituent such as alky l or ary l. [4] They arise
from or can be generated by a number of
routes, but the principal method is H-atom
abstraction from thiols. Another method
inv olv es homoly sis of organic disulfides. [30]
In biology thiy l radicals are responsible for
the formation of the deoxy ribonucleic acids,
building blocks for DNA. This conv ersion is
cataly sed by ribonucleotide reductase (see
figure). [31] Thiy l intermediates also are
produced by the oxidation of glutathione, an
antioxidant in biology . Thiy l radicals are also
intermediates in the v ulcanization process. The catalytic cycle for ribonucleotide reductase, demonstrating the
For example, the v ulcanization of role of thiyl radicals in producing the genetic machinery of life.
poly isoprene results when mercapto radicals
couple forming disulfide and poly sulfide
crosslinks. Thiy l radicals (sulfur-centred) can transform to carbon-centred radicals via hy drogen atom exchange
equilibria. The formation of carbon-centred radicals could lead to protein damage v ia the formation of C–C bonds or
backbone fragmentation. [32]

Biological importance

Cysteine and cystine


As the functional group of the amino acid cy steine, the thiol group play s a v ery important role in biology . When the
thiol groups of two cy steine residues (as in monomers or constituent units) are brought near each other in the
course of protein folding, an oxidation reaction can generate a cy stine unit with a disulfide bond (–S–S–). Disulfide
bonds can contribute to a protein's tertiary structure if the cy steines are part of the same peptide chain, or
contribute to the quaternary structure of multi-unit proteins by forming fairly strong cov alent bonds between
different peptide chains. A phy sical manifestation of cy steine-cy stine equilibrium is prov ided by hair straightening
technologies. [33]

Sulfhy dry l groups in the activ e site of an enzy me can form noncov alent bonds with the enzy me's substrate as well,
contributing to cov alent cataly tic activ ity in cataly tic triads. Activ e site cy steine residues are the functional unit in
cy steine protease cataly tic triads. Cy steine residues may also react with heav y metal ions (Zn2+ , Cd2+ , Pb 2+ , Hg2+ ,
Ag+ ) because of the high affinity between the soft sulfide and the soft metal (see hard and soft acids and bases). This
can deform and inactiv ate the protein, and is one mechanism of heav y metal poisoning.

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Cofactors
Many cofactors (non-protein-based helper molecules) feature thiols. The biosy nthesis and degradation of fatty acids
and related long-chain hy drocarbons is conducted on a scaffold that anchors the growing chain through a thioester
deriv ed from the thiol Coenzy me A. The biosy nthesis of methane, the principal hy drocarbon on Earth, arises from
the reaction mediated by coenzy me M, 2-mercaptoethy l sulfonic acid. Thiolates, the conjugate bases deriv ed from
thiols, form strong complexes with many metal ions, especially those classified as soft. The stability of metal
thiolates parallels that of the corresponding sulfide minerals.

In skunks
The spray of skunks consists mainly of low-molecular-weight thiols and deriv ativ es. These hav e a foul odor that
protects skunks from predators such as humans and wolv es. Owls can prey on skunks as they do not hav e a sense of
smell[34] and are therefore not deterred.

Examples of thiols
Methanethiol – CH3SH [methyl mercaptan] Coenzyme A
Ethanethiol – C2H5SH [ethyl mercaptan] Glutathione
1-Propanethiol – C3H7SH [n-propyl mercaptan] Metallothionein
2-Propanethiol – CH3CH(SH)CH3 [2C3 mercaptan] Cysteine
2-Mercaptoethanol
Allyl mercaptan – CH2=CHCH2SH [2-propenethiol]
Dithiothreitol/dithioerythritol (an epimeric pair)
Butanethiol – C4H9SH [n-butyl mercaptan]
2-Mercaptoindole
tert-Butyl mercaptan – (CH3)3CSH [t-butyl mercaptan]
Grapefruit mercaptan
Pentanethiols – C5H11SH [pentyl mercaptan] Furan-2-ylmethanethiol
Thiophenol – C6H5SH 3-Mercaptopropane-1,2-diol
Dimercaptosuccinic acid 1-Hexadecanethiol
Thioacetic acid Pentachlorobenzenethiol

See also
Doctor sweetening process
Odorizer
Thiol-disulfide exchange

Footnotes

References
1. Dictionary Reference: thiol (http://dictionary.reference.com/browse/thiol)
2. θεῖον (http://www.perseus.tufts.edu/hopper/text?doc=Perseus%3Atext%3A1999.04.0057%3Aentry%3Dqei%3Don1),
Henry George Liddell, Robert Scott, A Greek –English Lexicon
3. Patai, Saul, ed. (1974). The chemistry of the thiol group. London: Wiley. ISBN 0-471-66949-0.
4. R. J. Cremlyn (1996). An Introduction to Organosulfur Chemistry. Chichester: John Wiley and Sons. ISBN 0-471-95512-
4.
5. Dictionary Reference: mercaptan (http://dictionary.reference.com/browse/mercaptan)

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6. Oxford American Dictionaries (Mac OS X Leopard).


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because it reacted violently with mercury(II) oxide ("deutoxide de mercure") [p. 92]. See:
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=1Jc5AAAAcAAJ&pg=PA87#v=onepage&q&f=false) [On mercaptan; with observations on other products resulting
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ethylene polymers] on metal sulfides]. Annales de Chimie et de Physique. 56: 87–97.
The article in Annales de Chimie et de Physique (1834) was translated from the German article: Zeise, W. C. (1834).
"Das Mercaptan, nebst Bemerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf
weinschwefelsaure Salze und auf das Weinöl" (https://books.google.com/books?id=wCUAAAAAMAAJ&pg=PA369#
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072402).
The article in Annalen der Physik und Chemie (1834) was translated from the original Danish article in: Zeise (1834).
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Verlag, Weinheim. doi:10.1002/14356007.a26_767 (https://doi.org/10.1002%2F14356007.a26_767)
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34. https://theowlstrust.org/owl-hub/owl-education-programmes/understanding-owls/

External links
Mercaptans (or Thiols) (http://www.periodicvideos.com/videos/mv_smelly.htm) at The Periodic Table of Videos
(University of Nottingham)

https://en.wikipedia.org/wiki/Thiol#Reactions 9/10
4/27/2018 Thiol - Wikipedia

Applications, Properties, and Synthesis of ω-Functionalized n-Alkanethiols and Disulfides – the Building Blocks of Self-
Assembled Monolayers (http://dysa.northwestern.edu/CurrOrgChem.pdf) by D. Witt, R. Klajn, P. Barski, B.A.
Grzybowski at Northwestern University.
Mercaptan (http://www.factmonster.com/ce6/sci/A0832739.html), by The Columbia Electronic Encyclopedia.
What is Mercaptan? (http://www.columbiagaspamd.com/community_outreach/mercaptan.htm), by Columbia Gas of
Pennsylvania and Maryland.
What Is the Worst Smelling Chemical? (http://chemistry.about.com/od/chemistryfaqs/f/blsmell.htm), by About
Chemistry.

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