Electrostatic Potentials of Amine Nitrogens as a Measure of the Total Electron-Attracting Tendencies of Substituents

摘要

A direct computational means for obtaining a measure of a substituent's total electron attracting tendency is presented; it involves the calculation of ab initio SCF molecular orbital wavefunctions and electrostatic potentials of substituted amines. The results indicate that the nitrogen lone-pair potential minima of NH2-X molecules provide a quantitative index of the total electron-attracting tendencies of the substituents X. A good correlation is shown to exist between the amine potential minima in a group of twenty four NH2-X molecules and the sum of the inductive and resonance substituent constants, sigma1 and sigma, for sigma = 0. Reprints. (MJM)