
TY  - JOUR
A1  - Bouma, WJ 
A1  - Radom, L 
T1  - Keto-enol tautomerism. Relative stabilization of enol isomers
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 6
SP  - 1167
EP  - 1176
KW  - 
UR  - https://doi.org/10.1071/CH9781167 
N2  - 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. 
ER  -

