ChemInform Abstract: Relative Basicities of Some endo and exo Norbornylamines.

Abstract

Relative Basicities of Some endo and exo Norbornylamines.-A series of 2 exo-substituted norbornanes with tertiary amine substituents (I) and the corresponding endo isomers are synthesized in a manner previously reported, and their relative basicities are determined in acetonitrile and DMF. The exo isomer is always more basic than the corresponding endo isomer in either solvent. All of the bicyclic amines studied have higher pKa's in MeCN than in DMF except for the morpholino derivative. The results of semiempirical calculations of proton affinities and dipole moments correspond well with the experimental observations. -(COOK, A. G.; WESNER, L. R.; FOLK, S. L.; J.