A Translator’s Guide to Organic Chemical

Nomenclature
Part XIII

by Chester E. Claff, Jr., Ph. D.

Download the zipped version of the first installments of this series, originally published in the Sci-Tech
Translation Journal, of the American Translators Association. The file is approximately 87 KB.

Previous installments of this series appeared in the July 1997, October 1997, January 1998, April 1998, and July
1998 issues of the Translation Journal.

VI. Organic Sulfur Compounds (continued)

Thials, Thiones, and Thiocarboxylic Acids

Some examples of the sulfur analogs of aldehydes, ketones, and

carboxylic acids are shown below:

Oxygen compounds
CH3CH2CH2CHO Butyraldehyde, or butanal
CH3C(O)C2H5 Methyl ethyl ketone, or butanone
CH3CH2C(O)OH Propionic acid, or propanoic acid
HOC(O)CH2C(O)OH Propanedicarboxylic acid, or malonic acid

Sulfur analogs
CH3CH2CH2CHS Butanethial
CH3C(S)C2H5 Methyl ethyl thioketone, or butanethione
CH3CH2C(S)OH Propanethioic O-acid
CH3CH2C(O)SH Propanethioic S-acid
CH3CH2C(S)SH Propanedithioic acid
HSC(S)CH2C(S)SH Propanebis(dithioic) acid

Oxidized Organic Sulfur Compounds

We have seen that some organic oxygen compounds have sulfur

analogs: alcohols ROH  mercaptans RSH; ethers ROR'  sulfides RSR';
peroxides ROOR'  disulfides RSSR', and we have just looked at some
sulfur analogs of aldehydes, ketones, and carboxylic acids. However,
because sulfur compounds can readily be oxidized, there are further
classes of sulfur compounds with no oxygen analogs.

Dimethyl sulfide CH3SCH3 can be oxidized in stages to form two new

compounds:

Dimethyl
Dimethyl
sulfoxide
sulfone
DMSO

Sulfolane is a cyclic sulfone that is useful as a solvent:

Oxidation of methyl mercaptan also proceeds stepwise:

Methanesulfenic Methanesulfinic
acid acid
Methanesulfonic
acid

Alkanesulfenic acids are unstable and cannot usually be isolated, but

sulfinic acids and sulfonic acids are stable compounds. The simpler sulfur
acids are given radicofunctional names as shown above, but substitutive
nomenclature may be more convenient for complex compounds:

4-Methyl-2-sulfinopentane, or 3-Sulfo-4-decene, or
4-methyl-2-pentanesulfinic acid 4-decene-3-sulfonic acid
Of course these acids can form salts and esters:
CH3CH2S(O)ONa Sodium ethanesulfinate (a salt)
CH3S(O2)OC2H5 Ethyl methanesulfonate (an ester)

Halides and anhydrides of sulfinic and sulfonic acids also exist:

CH3CH2CH2S(O)Br Propanesulfinyl bromide
CH3S(O2)OS(O2)CH2CH3 Methanesulfonic ethanesulfonic
anhydride

3-Sulfopropionic anhydride

When some of the oxygen atoms attached to the sulfur atom in these
compounds are replaced by sulfur atoms, the prefix thio- (with
appropriate multiplier) is used:
 Methanemonothiosulfonic O-acid

Methanedithiosulfonic S-acid

Fortunately for translators, such compounds are rarely encountered in

the literature.

Before leaving the subject of sulfur compounds, a comparison of the

nomenclature of sulfuric acid derivatives and sulfonic acid derivatives
would not be out of place. As a dibasic (inorganic) acid, sulfuric acid
HOS(O2)OH can form monoesters, diesters, and salts, all of which are
called sulfates. The esters and salts of sulfonic acids are of course called
sulfonates. At first glance their formulas may appear similar; they are
differentiated by the fact that only sulfonates have a carbon-to-sulfur
bond:

CH3OS(O2)OCH3 Dimethyl sulfate (a diester of sulfuric acid)

CH3S(O2)OCH3 Methyl methanesulfonate (an ester of
methanesulfonic acid)
NaOS(O2)OC12H25 Sodium lauryl sulfate (a salt/ester of sulfuric
acid, and a widely used surfactant)

VII. Alicyclic Compounds

Although other derivatives in the alkane series remain to be discussed,

especially nitrogen compounds, the descriptions given so far of the
compounds of carbon, hydrogen, halides, oxygen, and sulfur in their
infinite variety permit us to expand our considerations to compounds in
which the carbon atoms form rings.
The underlying cycloalkane series CnH2n, begins with cyclopropane C3H6:

= Cyclopropane
 Cyclobutane

Cyclopentane

Cyclohexane

Cycloheptane

Cyclooctane, and so on.

Naturally, there are also cyclalkenes:

Cyclobutene

Cyclopentadiene

Cyclooctatetraene, and so on.

The case of cyclohexatriene (benzene) needs special consideration and

will be discussed later in the section on aromatic compounds.

The alicyclic family also includes the same derivatives as the acyclic
compounds, for example:

Chlorocyclohexane

Cyclopentanone
 Cyclobutenol

Cyclopropanecarbaldehyde

Cyclopentanecarboxylic acid

Methyl 1,3-cyclopentadiene-5-carboxylate

Part XIV will continue the discussion of alicyclic compounds.

Readers are urged to e-mail questions, comments, or suggestions for

further topics in the field of organic nomenclature to the author at:
74654.1335@compuserve.com.

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