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Nuclear Magnetic Resonance Spectroscopy. Conformational Equilibria and Equilibration of 4,4-Difluoropiperidine. Measurement of the N-H Inversion Rate in a Six-Membered Ring

Yousif, Garib A. and Roberts, John D. (1968) Nuclear Magnetic Resonance Spectroscopy. Conformational Equilibria and Equilibration of 4,4-Difluoropiperidine. Measurement of the N-H Inversion Rate in a Six-Membered Ring. Journal of the American Chemical Society, 90 (23). pp. 6428-6431. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151013-145415753

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Abstract

Fluorine magnetic resonance spectroscopy has been used to measure the rates of inversion of 4,4-difluoropiperidine. The activation energy (E_s) was found to be 13.9 and 13.5 kcal/mol in methanol and chloroform, respectively. In acetone, N-H nitrogen inversion was found to be slow on the nmr time scale with an E_s of about 10 kcal/mol. The free-energy difference between the forms with the N-H hydrogen axial and equatorial appears to be 0.42 kcal/mol with uncertain sign.


Item Type:Article
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http://dx.doi.org/10.1021/ja01025a033DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01025a033PublisherArticle
Additional Information:© 1968 American Chemical Society. Received March 9, 1968. Supported by the National Science Foundation. We are deeply indebted to Dr. J. Edgar Anderson and Mr. Frank J. Weigert for many valuable suggestions and help with both the taking of the spectra and the computations of the rates.
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Caltech Gates and CreIIin Laboratories of Chemistry3627
Issue or Number:23
Record Number:CaltechAUTHORS:20151013-145415753
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151013-145415753
Official Citation:Nuclear magnetic resonance spectroscopy. Conformational equilibria and equilibration of 4,4-difluoropiperidine. Measurement of the N-H inversion rate in a six-membered ring Garib A. Yousif and John D. Roberts Journal of the American Chemical Society 1968 90 (23), 6428-6431 DOI: 10.1021/ja01025a033
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61084
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:14 Oct 2015 19:46
Last Modified:03 Oct 2019 09:04

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