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The structure of the carboxyl group. I. The investigation of formic acid by the diffraction of electrons

Pauling, Linus and Brockway, L. O. (1934) The structure of the carboxyl group. I. The investigation of formic acid by the diffraction of electrons. Proceedings of the National Academy of Sciences of the United States of America, 20 (6). pp. 336-340. ISSN 0027-8424. http://resolver.caltech.edu/CaltechAUTHORS:PAUpnas34a

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Abstract

The electronic structure of a carboxylic acid has been ordinarily written as [diagram]. It has been recognized,(1) however, that the structure O:- R:C::O+:H also may make a significant contribution to the normal state of the molecule, and the existence of such resonance of the double bond between the two oxygen atoms has been supported by thermochemical data,(2) the resonance energy being 1.20 v.e. for the carboxyl group in acids and in esters. During the investigation reported in this paper we have verified the resonating structure by the determination of interatomic distances in formic acid, and have also shown that in the dimer of formic acid the molecules are joined together by hydrogen bonds between the oxygen atoms of the carboxyl groups.


Item Type:Article
Additional Information:© 1934 by the National Academy of Sciences. Communicated May 8, 1934. We are indebted to Dr. S. Weinbaum for many of the calculations involved in this investigation.
Record Number:CaltechAUTHORS:PAUpnas34a
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:PAUpnas34a
Alternative URL:http://www.pnas.org/cgi/reprint/20/6/336
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:10080
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:10 Apr 2008
Last Modified:14 Nov 2014 19:20

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