ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 23, Number 5
JKCSEZ 23(5)
October 20, 1979 

CNDO/2 calculations on XC6H4CH2Cl, where X = H, p-CH3, p-NH2 and p-NO2, and on benzyl radicals, cations and anions have been carried out in order to investigate nonlinear Hammett behavior. Main conclusions reached are: 1. Benzyl chloride exhibits borderline behavior due to σ-π conjugation between C-Cl bond and the ring-system. 2. The extent of mutual conjugation can be judged by π-charge and bond alternation and interfrontier level separation narrowing effects. 3.The electron donating para substituent reduces the HOMO AO coefficient of the benzylic carbon, while the electron withdrawing para substituent reduces the LUMO AO coefficient of the benzylic carbon.