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6LC Anodes for the electrolytic industry are unif orm — they stand the test of comparison.
ELECTRODE DIVISION
Manufacturers of graphite anodes • graphite and amorphous carbon electrodes •carbon and graphite specialties. Main Office Niagara Falls N Y. Plants: Niagara Falls, N.Y and Morgan!on,N C. • Sales office in principal cities •
C H E M I C A L REAGENTS • Semicarbazide HCI
White crystals, freely soluble in water. Use: Wi l l form Semicarbazones with Aldehydes and Ketones.
• Thiosemicarbazide White crystals, moderately water-soluble. Use: Similar to Semicarbazide HCL, also in preparation of therapeutic Thio-semicarbazones.
• Thio Michler's Ketone Tetramethyldiamino Thi obenzophenone. Use: Reasent for heavy metals forming complex salts (Hg).
• Iodic Anhydride White crystals, freely soluble in water. Use: Strong oxidizing agent. Determination of Carbonrnonoxide in gas analysis.
• Hydrazine Base • Hydrazine Hydrate Hydrazine Sulfate
• Sodium Azide • Sodium Cyanate Boron Nitride
N O M E N C L A T U R E
WORDS ABOUT WORDS
C H E M I C A L C O . , I N C . 600 Ferry St., Newark 5, N. J.
Organic Phosphorus Compounds Something had to be done. Phosphorus
compounds were growing in number and importance and their names were in an unsatisfactory state. The Committee on Nomenclature of«the ACS Division of Organic Chemistry appointed an advisory group to study the matter. For over two years this group has worked intensively under the chairmanship of L, R. Drake of the Dow Chemical Co. and has now produced a report. The group consists at present of 29 persons, including both organic* and inorganic chemists, industrialists and teachers, Americans and Britons. A special committee of the London Chemical Society has cooperated. Concessions and compromises have resulted in what is believed to be a consistent system. W e can give only a sketch of the 34-page report, which contains (for committee use) the old and new names of 300 phosphorus compounds.
General Principles In the United States the following names
have been in use for four acids important for their organic derivatives: HPO(OH)a, phosphonic; HzPO.OH, phosphinic; HP-(OH)a, phosphonous; and H*POH, phos-phinous. The British, whose practice differed somewhat, have accepted these names. The Americans in their turn have given up "additive" names (of the type benzenephosphonic) in favor of "substitutive" names (of the type phenylphos-phonic).
For derived phosphorus acids, in which OH is replaced by an inorganic group, Americans have favored names of the type chlorophosphoric acid for ClPO(OH) 8 , while Britons preferred chlorophosphonic acid for this compound; that is, the former regarded chlorine as replacing OH, while the latter treated it as replacing H. As neither side cared to yield to the other, a compromise was found in new names of the type phosphorochloridic acid for ClPO(OH) 2 and phosphorochloridous acid for ClP(OH) 2 ; that is, the word element which denotes the modifying inorganic atom or group is inserted in the name of the parent compound, just before the -ic or -ous ending. This plan is carried all the way through and a list of "affixes" is given, as amid(o) - , chlorid(o)- , cya-n id(o) - , nitrid(o)-, for such insertion. In the case of an organophosphorus name the organic part can then be prefixed without risk of ambiguity.
Monophosphorus Compounds The name phosphine is retained for PHa
and its organic derivatives are named in the usual way, as trimethylphosphine. HaPO is phosphine oxide, HaPS is phos-
0 221 North King St., Xenia, Ohio.
AUSTIN M . PATTERSON*
phine sulfide. P l i i is phosphorane (not phosphane, as the latter name is used in the series diphosphane, triphosphate, and so on; see be low) . The names of acids in which phosphorus is trivalent end in -ous; quinquevalent, in -ic. Examples: phosphorous, phosphonous, phosphinous, phos-phenous(OPOH), phosphoric, phosphonic, phosphinic; phosphenic, OaPOH; phos-phoranoic, HJPOH; phosphoranedioic, HsP(OH)a. Phosphonium is retained for H4P*. Miscellaneous examples: EtzPOH, diethylphosphinous acid; HPO, oxophos-phine; HPS2, thionophosphine sulfide; POCla, phosphoric trichloride; M e P ( O ) -Cl ( N H 2 ) , methylphosphonamidic chloride. Examples of radical names: HsP—, phosphino; H 2 P ( 0 ) — , phosphinyl; HaP-( N H ) —, phosphinimyl; MeOP( O ) = , methoxyphosphinylidene; O P = , phosphin-ylidyne. Ester name: HSP(S) (OEt)* , O,0-diethyl hydrogen phosphorodithidate.
Polyphosphorus Compounds Although the existing names pyrophos-
phoric (or diphosphoric), triphosphoric, tetraphosphoric are not supplanted, there is need for a more general system for naming compounds containing more than one atom of phosphorus. This can be based, as first suggested by G. M. Steinberg, on the precedent set by International Union rule 43f of the organic definitive report [/. Am. Chem. Soc, 55, 3919 ( 1 9 3 3 ) ] for nitrogen compounds. Accordingly, H*P-PH2 is diphosphane, H2P.PH.PH2 is tri-phosphane, HaP.P:PH is triphosphene, H2P.PH.PH.PH2 is tetraphosphane, and so on. If quinquevalent phosphorus forms part of such a chain its nature is indicated by "dihydro" or by an additive prefix, thus: HP:PH2.PH.PH2, 2,2-dihydro-l-tetraphos-phene; H2P.P(0) (OH) .PH 2 , 2-hydroxy-2-oxidotriphosphane. Since the adding of a suffix to these names has been found to result in complications all functional groups are denoted by prefixes.
The "phosphane" names can be extended to rings; for example, a ring of six PH groups can be called cyclohexaphosphane; also, with the aid of the "a" (or "oxa-aza") nomenclature, they can be extended to mixed chains and rings; for example, CHaCH2.PH.O.PH.NH.PHCH3 is called 1 - ethyl - 5 - methyl - 2 - oxa - 4 - aza-pentaphosphane (the fundamental chain begins and ends with a phosphorus atom).
The group believes it has provided systematic names over*a wider range thf n has hitherto been possible. It has tried to choose names which fit in with other organic and inorganic nomenclature and which can be understood and used by chemists who are not specialists in the organophosphorus field. The system would have the advantage that a larger number of names would be indexed under Phosph-and so be grouped together. Analogous
2336 C H E M I C A L A N D E N G I N E E R I N G N E W S
«iftmount
NIAGARA FALLS, Ν. Υ.
Uniform
names can be used tor compounds ol arsenic, antimony, and possibly bismuth.
The report has been reviewed and accepted by the committee of the ACS Division of Organic Chemistry and will ultimately be reviewed by national (and, it is hoped, international) committees. In any case the group has performed an admirable piece of work in harmonizing conflicting names and greatly extending the field of coverage.
The British Position Editor R. S. Cahn of the (,London)
Chemical Society has asked me to append the following statement: "The British Subcommittee on Organophosphorus Nomenclature has agreed to the proposals for compounds containing one atom of phosphorus but has suggested certain modifications of the polyphosphorus nomenclature. British adoption of the new nomenclature for compounds containing one phosphorus atom is subject to approval by the Publication Committee of the Chemical Society, and its use in the Chemical Society publications will await final approval of both the British and the American Chemical Societies."
Woodman, Spare That Long W o r d !
A biochemist is much concerned about the length of some of our organic words, thinks they are grammatically incorrect, and would break them up into separate words. W e agree that they are often long and mystifying to outsiders, but if properly constructed they are exact and not grammatically wrong. Breaking them up into shorter units would often change or confuse the sense. Blame for the length of chemical names must rest on the complexity of the compounds which they describe. In such a complicated subject one must understand the rules of the game, of course. There is room for simplification of the rules, and they are being improved, but no one should expect a system for correctly describing an intricate chemical structure in a short word or phrase. In 1931 the ACS adopted a report on the written form of chemical words which has remained a standard ever since; see / . Am. Chem. Soc, Proc, 40 -1 ( 1 9 3 1 ) , or / . Chem. Education, 8, 133B-8 ( 1 9 3 1 ) . Reprints of this report are available from the office of Chemical Abstracts.
"Strings of Numbers'1
G. M. Dyson, commenting on the Feb. 4 issue of this column (page 4 6 0 ) , thinks that 1-7 as a short expression for 1,2,3,4,5,6,7 is "quite inadmissible" because it is already in use to denote direct union between positions 1 and 7. H e would perhaps (although he does not say so) use 1 ( 1 ) 7 as in his cipher system. H e also thinks that a subscript might be used to indicate a number of identical locants; for example, 1,1,1,2,2,3,3,4-octachloro-might be written l«,22,3a,4-octachloro-. R. W. Hakala has made the same suggestion. It's worth considering.
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