
%0 Journal Article
%A Bouma, WJ 
%A Radom, L 
%T Keto-enol tautomerism. Relative stabilization of enol isomers
%J Australian Journal of Chemistry
%D 1978/06/01
%V 31
%N 6
%P 1167-1176
%K 
%R https://doi.org/10.1071/CH9781167
%U https://www.publish.csiro.au/paper/CH9781167 
%X Ab initio molecular orbital theory is used to examine the effect of simple &#960;-electron-accepting substituents (Li, BeH, BH2) on the keto-enol equilibrium in the acetaldehyde-vinyl alcohol system. The enol-keto energy difference is increased slightly by &#945;-Li substitution and decreased to a near-zero value by a BH2 substituent. The results are rationalized in terms of geminal interactions. The conformational preferences of substituted acetaldehyde systems (XCH2CHO; X = Li, BeH, BH2, CH3, F) are discussed. Three classes of rotational potential functions are distinguished on the basis of the &#963;-electron-donating or -accepting nature of the substituent. 
