Conformational features of benzoyl N-alkylated amino-acids (N-alkylated benzamido-acids) determined by nuclear magnetic resonance spectroscopy
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 11,p. 1157-1163
- https://doi.org/10.1039/p29780001157
Abstract
cis–trans Rotational isomerism about the benzoyl amide bond has been detected in a series of N-alkylated benzamido-acids. The proportions of cis–trans rotamers appear to be different for N-methylvaline and N-methylisoleucine when compared with other imino-acids studied. A singlet peak for the aromatic protons in the 1H n.m.r. spectra of a number of derivatives, shows that the ortho-protons are not deshielded and that conjugation between the benzene ring and the amide group is reduced because of the steric environment created by N-alkylation of the amide. U.v. measurements also confirm this phenomenon.Keywords
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