American Chemical Society
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Isomeric Solid Enols on Ring- and Amide-Carbonyls of Substituted 2-Carbanilido-1,3-indandiones

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posted on 2007-10-11, 00:00 authored by Jinhua Song, Masaaki Mishima, Zvi Rappoport
Both isomeric enols on ring carbonyl (5b) and on amide carbonyl (6b) derived from N-p-methoxyphenyl-2-carbamido-1,3-indandione (4b) were isolated, and their X-ray structures were determined. X-ray diffraction of the N-o,p-dimethoxy analogue indicated a disorder ascribed to the presence of a 6:4 mixture of 5c and 6c. Calculation (B3LYP/6-31+G*) gave good agreement with observed geometries. The calculated energies indicated that enols 6 are more stable by <1 kcal/mol than enols 5 and much more stable than amides 4.