ISSN:
0894-3230
Keywords:
enol of acetoacetic acid
;
relative stability
;
computational study
;
Chemistry
;
Theoretical, Physical and Computational Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Ab initio molecular orbital calculations at the MP2/6-311+G**//MP2/6-311+G** level show that the enol tautomer of acetoacetic acid in which the ketone group is enolized, 2, is more stable than its isomer in which the carboxylic acid group is enolized, 3, by 11·3 kcal mol-1. This difference may be attributed to a difference in the strength of resonance interactions between the carbonyl and hydroxyl groups of the enols: the carbonyl group in both isomers is conjugated with two hydroxyl groups, but in the acid enol, 3, both interactions are vinylogous, whereas in the ketone enol, 2, one of the vinylogous effects is replaced by a stronger direct interaction. © 1997 by John Wiley & Sons, Ltd.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
Permalink
