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Issue 9, 2000

Configurational assignments of diastereomeric γ-lactones using vicinal H–H NMR coupling constants and molecular modelling

Author affiliations

Abstract

The conformational features of four diastereomers of the γ-lactone 2-ethyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid were investigated by calculations which included molecular mechanics (MM3), semiempirical (AM1) and ab initio molecular orbital theory (HF/6-31G), the latter including solvent emulation. Results were compared with those obtained by 1H NMR spectroscopy of natural and synthetic analogues in which a long aliphatic chain replaces the ethyl side chain. A notable agreement was found between the experimental vicinal ring coupling constants and those computed by the ab initio calculation; MM3 also gave rise to a fair agreement, while AM1 shows large failures to encounter the potential energy surface of these and other five-membered rings.

Supplementary files

Article information


Submitted
15 May 2000
Accepted
05 Jul 2000
First published
09 Aug 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 1832-1836
Article type
Paper

Configurational assignments of diastereomeric γ-lactones using vicinal H–H NMR coupling constants and molecular modelling

C. A. Stortz and M. S. Maier, J. Chem. Soc., Perkin Trans. 2, 2000, 1832 DOI: 10.1039/B003862H

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