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^(15)N Nuclear Magnetic Resonance Spectroscopic Investigation of Differential Rates of Base-Catalyzed N-H Proton-Exchange Reactions of 1-aza-2-Cycloheptanone and 1-aza-2-Cycloheptanethione

Yavari, Issa and Roberts, John D. (1978) ^(15)N Nuclear Magnetic Resonance Spectroscopic Investigation of Differential Rates of Base-Catalyzed N-H Proton-Exchange Reactions of 1-aza-2-Cycloheptanone and 1-aza-2-Cycloheptanethione. Tetrahedron Letters, 19 (28). pp. 2491-2494. ISSN 0040-4039. https://resolver.caltech.edu/CaltechAUTHORS:20151023-101624619

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Abstract

Natural-abundance proton-coupled ^(15)N NMR spectra of an equimolar solution of the title compounds in dimethyl sulfoxide, to which was added aqueous sodium hydroxide, show that N-H proton exchange of the thiolactam is about 1500 times faster than that of the lactam at 25°C. This rate difference is suggested to arise from a greater contribution of the polar resonance structure for the thiolactam.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/S0040-4039(01)94808-7DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403901948087PublisherArticle
Additional Information:© 1978 Pergamon Press Ltd. Received in USA 18 April 1978; received in UK for publication 16 May 1978. Supported by the National Science Foundation, and by the Public Health Service, Research Grant No. GM-11073 from the Division of General Medical Sciences.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
U.S. Public Health Service (USPHS)GM-11073
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Caltech Gates and Crellin Laboratories of Chemistry5764
Issue or Number:28
Record Number:CaltechAUTHORS:20151023-101624619
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151023-101624619
Official Citation:Issa Yavari, John D. Roberts, 15N nuclear magnetic resonance spectroscopic investigation of differential rates of base-catalyzed N-H proton-exchange reactions of 1-aza-2-cycloheptanone and 1-aza-2-cycloheptanethione, Tetrahedron Letters, Volume 19, Issue 28, 1978, Pages 2491-2494, ISSN 0040-4039, http://dx.doi.org/10.1016/S0040-4039(01)94808-7. (http://www.sciencedirect.com/science/article/pii/S0040403901948087)
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ID Code:61480
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:53
Last Modified:03 Oct 2019 09:08

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