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Steric and Electronic Effects on ^(15)N Chemical Shifts of Saturated Aliphatic Amines and Their Hydrochlorides

Duthaler, Rudolf O. and Roberts, John D. (1978) Steric and Electronic Effects on ^(15)N Chemical Shifts of Saturated Aliphatic Amines and Their Hydrochlorides. Journal of the American Chemical Society, 100 (12). pp. 3889-3895. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151008-070942553

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Abstract

Natural-abundance ^(15)N NMR chemical shifts of saturated aliphatic primary, secondary, and tertiary amines and their hydrochlorides have been measured in different solvents. Good linear correlations of these ^(15)N shifts with the ^(13)C shifts of carbons in the same positions in the corresponding hydrocarbon analogues were only found for the primary compounds. The degree of correlation between ^(l5)N and ^(13)C shifts decreased successively with secondary to tertiary amines and their hydrochlorides. Despite this, sets of solvent-dependent additive shift parameters were derived which give reasonably satisfactory agreement between calculated and experimental shifts of all of the amines and hydrochlorides. Some of the substituent-induced shifts appear to be conformational effects and can be compared with substituent effects observed previously for cyclic amines. The generally downfield protonation shifts could also be correlated with empirical substituent parameters.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ja00480a038DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00480a038PublisherArticle
Alternate Title:Steric and electronic effects on nitrogen-15 chemical shifts of saturated aliphatic amines and their hydrochlorides
Additional Information:© 1978 American Chemical Society. Received August 20, 1977. We are indebted to Professor M. Allen for a convenient computer program for the least-squares multilinear regression analysis. Supported by the National Science Foundation and by the Public Health Service, Research Grant GM-11072 from the Division of General Medical Sciences.
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry5654
Issue or Number:12
Record Number:CaltechAUTHORS:20151008-070942553
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151008-070942553
Official Citation:Steric and electronic effects on nitrogen-15 chemical shifts of saturated aliphatic amines and their hydrochlorides Rudolf O. Duthaler and John D. Roberts Journal of the American Chemical Society 1978 100 (12), 3889-3895 DOI: 10.1021/ja00480a038
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60884
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:08 Oct 2015 18:09
Last Modified:03 Oct 2019 09:01

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