Stereoelectronic substituent effects in polyhydroxylated piperidines and hexahydropyridazines

HH Jensen, L Lyngbye, A Jensen…

Index: Jensen, Henrik Helligso; Lyngbye, Laila; Jensen, Astrid; Bols, Mikael Chemistry - A European Journal, 2002 , vol. 8, # 5 p. 1218 - 1226

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Citation Number: 85

Abstract

Abstract From the pK a values of the conjugate acids of a large series of hydroxylated piperidines and hexahydropyridazines, a consistent difference in basicity was found between stereoisomers having an axial or equatorial hydroxyl (OH) group either β or γ to the amine. Compounds with an equatorial OH group in the 3-position were 0.8 pH units more acidic than otherwise identical compounds with an axial OH group, whilst compounds with ...