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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

An ab initio approach to creating a simple stable enol

WJ Bouma and L Radom

Australian Journal of Chemistry 31(8) 1649 - 1660
Published: 1978

Abstract

Ab initio molecular orbital theory is used to examine the effect of four substituents (CN, NO2, NO and CHO) which are π-electron acceptors and σ-electron acceptors on the keto-enol equilibrium in the acetaldehyde/vinyl alcohol system. Each substituent destabilizes the keto isomer and stabilizes the enol isomer as desired and hence decreases the enol-keto energy difference. For the NO and CHO substituents, the effect is sufficiently large that the enol isomer is predicted to be slightly lower in energy than the keto form. The conformational preferences of the keto isomers are discussed in detail and a conformational potential energy map is presented for malondialdehyde.

https://doi.org/10.1071/CH9781649

© CSIRO 1978

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