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NOMENCLATURE

PETROUTE WAX

MELTING PENE· COLOR ACID SAP. POINT°F TRATION NPA NO. NO.

15 23 36 50

180 200 500 700 1035

» 180 min. 4 to 6

— 180 min. 4 to 6

| | 180 min. 5 to 7 M 180 rain. 3 to 5

4-5 14-16 50-60

4-5 20-25 55-65

5-6 30-35 75-85

dark 10-20 65-75

= ] 180 min. 15 max. 2-2-5 Nil 65-75

£ 190 min. 8 max. brown Nil 65-75

g 190 min. 8 max. 2-2.5 Nil 65-75

§ 190min. 4 max. 2-2£ Nil 65-75

S 195 min. 2 max. 2-23 Nil 65-75

Jet Black g 185 min. 11 to 16 black Nil

ESTAWAX20 [Ξ 210 min. 2 max. 3 max.

ESTA WAX 25 U 210 min. 2 max. 3 max.

65-75

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by Austin M. Patterson

Names for Charge-Carrying Substituent Groups

The following proposal has been pre­sented to the Committee .on Nomencla­ture of the ACS Division of Organic Chemistry by J. F. Bunnett of the Univer­sity of North Carolina, Chapel Hill, N. C. For earlier material on the topic see C&EN, 30, 2843 (1952), 32, 90, 1386 (1954).

In the naming of compounds, many structural features are indicated by the principal ending of the chemical name, while others are indicated by citing the names of substituent groups (as pre­fixes). For this kind of use, standard names (nitro, iodoso, formyl, etc.) have been promulgated for many substituent groups. Though devised for purposes of naming compounds, these names have come to be used in the chemical language in other ways. Thus, one speaks of properties of the hydroxy group in salicylic acid, or of the deac­tivating, meta-directing effect of the nitro group toward bromination. It is fortunate for chemists that their lan­guage includes standard names for many substituent groups; clarity and conciseness are gained by the availa­bility of these names.

However, when the chemist comes to discuss, for example, the acidity of the —NH3

+ group in the zwitterion of an amino acid, or the Hammett sigma con­stant of the —COO" group, conventions for the nomenclature of compounds fur­nish him little or no help. Since ionic structures have been granted prece­dence over all others in deciding what is the principal function to be denoted in the ending of a systematic name, the presence of the —NH3

+ of the —COO" group in a molecule is not indicated by a prefix citing its name as a substituent group. Consequently, standard names have not been devised for substituent groups which carry electrical charges.

The lack of standard names for such groups is a great handicap in many dis­cussions of chemical reactivity. Chem­ists frequently get around the difficulty by giving the formula for the group, as I have done above, but this is unsatis­fying in writing and completely un­satisfactory in speech. Sometimes, the —NH3* group has been called the "am­monium salt group," or simply the "ammonium" group; these names are on the one hand distressing because of their lack of parallelism with the names of most substituent groups, while on the other they introduce ambiguity be­cause "ammonium" is accepted to mean the NH4

+ ion.

221 North King St., Xenia, Ohio.

Recently, some of my colleagues and I suggested (1, 2) a system for naming positively charged substituent groups. The system is illustrated by the designa­tion "ammonio group" for — NH3

+ . The - N ( C H 3 ) 3

+ group is then the "tri-methylammonio" group. Analogously, —S(CH3)2

+ is called "dimethylsul-fonio," this name being derived from the name "sulfonio" for the hypothetical substituent —SH2

+. Continuing the analogy, the — IC6H5

+ group is "phenyliodonio," — OH2

+ is "oxonio" (for example, in the conjugate acids of alcohols acting as Br0nsted bases), —As ( C6H5 ) 3+ is "triphenylarsonio." These names have the several advan­tages of being unique, of being derived by a simple and straightforward proc­ess from the names of the ions which contain them, and of being parallel in form to the currently accepted names of many substituent groups.

There is likewise need fpr standard names for negatively charged substit­uent groups. The chemist is currently at a loss when he wishes to speak or write of the effect of the —O" group (in the phenoxide ion, for instance) on the rate of a reaction such as diazo coupling; he either uses the formula of the group, as I have done above, or de­scribes it as the "ionized hydroxy group." Neither alternative is very satisfactory. His language also fails him when he wishes to differentiate between the —S03H and the — S0 3 " groups; the former is called sulfo, but what about the latter? Standard names are also needed for the following groups: -COO", — SO*', As03H", As0 3 ", POsH", P 0 3 " -NH", - S - . And there are many others. Perhaps names such as "carboxido," "sulfinido," "arsonido," "arsondiido," etc., would be suitable. Perhaps others would be better.

It should be noted that in addition to their use in general discussions, names for charged groups would find specific use in the systematic naming of substi­tution reactions, regarding which I have submitted a separate proposal. For example, the replacement of —N(CH 3 ) 3

+ by —OCH3 in the reaction of p-nitrophenyl-trimethylammonium iodide with methoxide ion (3) can be described as "methoxydetrimethylam-moniation." For construction of this name, it was necessary to have a name for the - N ( C H 3 ) 3

+ group.

Bibliography 1. J. F. Bunnett and R. E. Zahler,

Chem. Rev., 49, 291 (1951). 2. J. F. Bunnett, F. Draper, P. R.

Ryason, P. Noble, R. G. Tonkyn, and R. E. Zahler, /. Am. Chem. Soc, 75, 642 ( 1953).

3. A. Zaki and H. Fahim, / . Chem. Soc, 1942, 270.

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