An Investigation of the Enolization and Isomeric Products Distribution in the Water Promoted Aldol Reaction of Tropinone and Granatanone

Table 4

Free energies of enolization of tropinone and granatanone computed at the B3LYP/6-31g(d) and B3LYP/6-311++g(3d,3p) (in parenthesis, italics) levels.

	of enolization ( – )
Ketone	Reaction medium	Without explicit H2O		With explicit molecule of H2O		Zwitterionic form	Hydrated zwitterionic form	With explicit molecule of PhCHO [24]
						The most stable N-invertomer
Tropinone	Gas	5.6; (4.9)	7.4; (6.5)	4.3; (5.4)	7.3; (6.6)	—	—	6.2
	Water (CPCM)	6.4; (6.2)	7.4; (7.2)	4.7; (6.8)	6.0; (7.5)	18.6; (14.4)	21.7; (20.2)	5.9
Granatanone	Gas	4.7; (3.5)	6.2; (5.4)	4.5; (4.1)	6.2; (7.6)	—	—	4.6
	Water (CPCM)	5.2; (5.2)	6.4; (6.3)	3.1; (5.7)	4.9; (6.0)	18.4; (15.9)	21.3; (22.0)	4.3

N-Me group position.