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The nitrile infrared intensities of a series of a,β-diaryl cyanoethylenes were juxtaposed to the associated substituent constants, HMO and SCF-MO indices and fair to excellent correlations were established. The competitive resonance of the nitrile group with alpha-and beta-aryl substituents is discussed. HMO calculations were used to estimate the steric hindrance to conjugation caused by polycyclic substituents and SCF-MO calculations were made to obtain uniform predictions of nitrile intensities and frequencies for hetero-cyclic derivatives of acrylonitrile.

Structural Effects on Nitrile Infrared Integrated Intensities of Alpha,Beta-Diaryl Cyanoethylenes: Hammett and Quantum Chemical Approaches