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The anomalous deuterium isotope effect on the chemical shift of the bridge hydrogen in the enol tautomer of 2,4-pentanedione

Chan, Sunney I. and Lin, L. and Clutter, Dale and Dea, Phoebe (1970) The anomalous deuterium isotope effect on the chemical shift of the bridge hydrogen in the enol tautomer of 2,4-pentanedione. Proceedings of the National Academy of Sciences of the United States of America, 65 (4). pp. 816-822. ISSN 0027-8424. http://resolver.caltech.edu/CaltechAUTHORS:CHApnas70

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Abstract

The nature of the intramolecular hydrogen bond in the enol tautomer of 2,4-pentanedione has been investigated by high resolution proton and deuteron magnetic resonance spectroscopy. An unusually large deuterium isotope effect on the chemical shift of the bridge hydrogen has been observed. This unexpected result, together with the observation of a pronounced temperature dependence for both the proton and deuteron resonances, suggests that two states with different chemical shifts for the bridge hydrogen are involved in rapid equilibrium and that the anomalous deuterium isotope effect has its origin in the effect of deuterium substitution on the energy separation between these states. It is proposed that these states correspond to the symmetrical and asymmetrical structures of the intramolecular hydrogen bond.


Item Type:Article
Additional Information:Copyright © 1970 by the National Academy of Sciences. Communicated by John D. Roberts, January 29, 1970. We wish to gratefully acknowledge the financial support of this research by the U.S. Public Health Service (grant GM-13212) and the National Science Foundation (grant GP-8540).
Record Number:CaltechAUTHORS:CHApnas70
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:CHApnas70
Alternative URL:http://www.pnas.org/cgi/content/abstract/65/4/816
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:1225
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:05 Jan 2006
Last Modified:26 Dec 2012 08:43

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