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The Electrical Effect of the Trimethylsilyl Group. II.

Roberts, John D. and Regan, Clare M. (1953) The Electrical Effect of the Trimethylsilyl Group. II. Journal of the American Chemical Society, 75 (16). pp. 4102-4103. ISSN 0002-7863. doi:10.1021/ja01112a528.

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In an earlier investigation, we presented evidence based on Hammett σ-constants that the trimethylsilyl [(CH_3)_3Si-] group is electron-donating in character as judged by the manner in which it influences the acidity of the carboxyl group in benzoic acid. Since the electrical influence of the group is not apparently clear-cut in other types of compounds we have reinvestigated the reactivities of the trimethylsilyl substituted benzoic acids and have prepared the corresponding ethyl esters and determined their alkaline saponification rates.

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Additional Information:© 1953 American Chemical Society. Received March 25, 1953. We have confined our attention to the acids and esters since Dr. R. A. Benkeser of Purdue University has measured the reactivities of a number of amine derivatives. ADDED IN PROOF.-R. A. Benkeser and H. R. Kryaiak, ibid., 76, 2421 (1953). The raults of these investigators with henzoic acid derivatives are in good agreement with those given in Table II.
Issue or Number:16
Record Number:CaltechAUTHORS:20151022-083818482
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Official Citation:The Electrical Effect of the Trimethylsilyl Group. II. John D. Roberts and Clare M. Regan Journal of the American Chemical Society 1953 75 (16), 4102-4103 DOI: 10.1021/ja01112a528
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61407
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 17:55
Last Modified:10 Nov 2021 22:48

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