Evaluation of the equilibrium and activation parameters for the interconversion of the conformational isomers of some N-acylprolines by nuclear magnetic resonance spectroscopy
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 6,p. 761-763
- https://doi.org/10.1039/p29760000761
Abstract
Study of the 1H n.m.r. spectra of six N-acyl-L-prolines (I)–(VI) over a range of temperatures has enabled the equilibrium and activation parameters for the interconversion of the cis- and trans-conformers to be evaluated. The energy barrier for the cis–trans-interconversion in (I), involving a urethane bond, is much lower than that for the other compounds, involving peptide bonds; the significance of this difference for the well known resistance of urethanes to racemisation in peptide synthesis is discussed.Keywords
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