Gas-phase structural (internal) effects in strong organic nitrogen bases

Abstract

Gas-phase basicities (GB) of strong organic bases containing the imino group were re-examined in the light of the re-evaluated GB values for the reference bases given in a recent compilation of Hunter and Lias. Structural (internal) effects which influence the basicity are discussed and general relations for the GB prediction are proposed for simple alkyl amidines and guanidines. These relations were used for estimation of cyclization and intramolecular H-bonding effects. Copyright © 2000 John Wiley & Sons, Ltd.