Volume 2, No. 4 
October 1998

Dr. Claff
A chemist-turned-translator, Dr. Claff earned his B.S. and Ph.D. degrees in Organic Chemistry at M.I.T. in 1950 and 1953. His academic and industrial research experience included the fields of organosodium chemistry, synthetic rubber, leather tanning and finishing, acrylic and vinyl polymerization, adhesives for coated abrasives, and flexographic printing inks. His career later evolved into corporate administration and management in metalworking, heart-lung machines, biological instrumentation, printing, personnel administration, and paper box manufacturing. His exposure to such diverse disciplines has been a valuable resource in his career as a freelance technical translator since 1974.
    Dr. Claff and his wife Eleanor make their home in Brockton, Massachusetts, with their Maine coon cats, DownE and Baxter.
   Dr. Claff can be reached at 74654.1335@compuserve.com



A Unique Medium
by Gabe Bokor
Index 1997-98
  Translator Profiles
May Your Neurons Never Get Tired of Your Challenges
by Steve Vlasta Vitek
  The Profession
The Bottom Line
by Fire Ant & Worker Bee
The Business of Translating
Danilo Nogueira
  Literary Translation
Translating Poetry/The Work of Arthur Rimbaud from French to English
by Michael Walker
  Art & Entertainment
Translator, a Lovely Profession
by Karin Almegård Nörby/Monica Scheer
Fernsehuntertitelung in Flandern
by Luc Ockers
 Biomedical Translation
Immunology—a Brief Overview, Part 2
by Lúcia M. Singer, Ph.D.
  Science & Technology
A Translator’s Guide to Organic Chemical Nomenclature XIII
by Chester E. Claff, Jr., Ph.D.
  Caught in the Web
Web Surfing for Fun and Profit
by Cathy Flick, Ph.D.
Translators’ On-Line Resources
by Gabe Bokor
Translators’ Events
Letters to the Editor
Call for Papers
Translation Journal

A Translator’s Guide to Organic Chemical Nomenclature


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)C2H5Methyl ethyl ketone, or butanone
CH3CH2C(O)OHPropionic acid, or propanoic acid
HOC(O)CH2C(O)OHPropanedicarboxylic acid, or malonic acid

Sulfur analogs
CH3CH2CH2CHS Butanethial
CH3C(S)C2H5Methyl ethyl thioketone, or butanethione
CH3CH2C(S)OHPropanethioic O-acid
CH3CH2C(O)SHPropanethioic S-acid
CH3CH2C(S)SHPropanedithioic acid
HSC(S)CH2C(S)SHPropanebis(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:

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

Oxidation of methyl mercaptan also proceeds stepwise:


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
4-methyl-2-pentanesulfinic acid
3-Sulfo-4-decene, or
4-decene-3-sulfonic acid

Of course these acids can form salts and esters:
CH3CH2S(O)ONaSodium 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)CH2CH3Methanesulfonic 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)OCH3Methyl methanesulfonate (an ester of methanesulfonic acid)
NaOS(O2)OC12H25Sodium 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:

Cyclooctane, and so on.

Naturally, there are also cyclalkenes:

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:

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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