Roberts, John D. and Regan, Clare M. (1954) Reactivities of 4-Substituted 2,6-Dimethylbenzoic Acids. Journal of the American Chemical Society, 76 (3). pp. 939-940. ISSN 0002-7863. doi:10.1021/ja01632a106. https://resolver.caltech.edu/CaltechAUTHORS:20151022-083818169
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Abstract
In an earlier investigation, it was found that the substituent effects in 4- and 5-substituted 2-methylbenzoic acids paralleled closely those obtained with benzoic acids without the 2-methyl group. One possible interpretation of the results is that in either series of acids, the reactivity of a carboxyl group is not importantly determined by resonance-coupling of the carboxyl group with various 4-substituents. The argument is not strong in view of the certainly limited ability of a single ortho-methyl group to reduce coupling by sterically forcing the carboxyl out of the plane of the aromatic ring. To gain further evidence on this point, we have determined the apparent ionization constants in 50% water-50% ethanol (by volume) at 25.0º and the reactivities toward diphenyldiazomethane in absolute ethanol at 30.0º of a series of 4-substituted 2,6-dimethylbenzoic acids (I).
| Item Type: | Article | |||||||||
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| Additional Information: | © 1954 American Chemical Society. Received June 15, 1953. Supported in part by the program of research of the U. S. Atomic Energy Commission. We are indebted to Dr. M. S. Newman for information in advance of publication about his own research on this problem, and to Dr. Newman and Dr. R. V. Heinzelman of the Upjohn Company for generous samples of the acids used in this work. | |||||||||
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| Issue or Number: | 3 | |||||||||
| DOI: | 10.1021/ja01632a106 | |||||||||
| Record Number: | CaltechAUTHORS:20151022-083818169 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151022-083818169 | |||||||||
| Official Citation: | Reactivities of 4-Substituted 2,6-Dimethylbenzoic Acids John D. Roberts and Clare M. Regan Journal of the American Chemical Society 1954 76 (3), 939-940 DOI: 10.1021/ja01632a106 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61406 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 22 Oct 2015 17:53 | |||||||||
| Last Modified: | 10 Nov 2021 22:48 |
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