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Int. J. Mol. Sci. 2004, 5(8), 224-238; doi:10.3390/i5050224
Article

Density Functional Studies of the Dipole Polarizabilities of Substituted Stilbene, Azoarene and Related Push-Pull Molecules

1,* , 1 and 2
1 The University of Manchester, School of Chemistry (North Campus), Sackville Street, Manchester M60 1QD, UK 2 Departamento de Química, Fac. Exp. de Ciencias, La Universidad del Zulia, Grano de Oro Módulo No. 2, Maracaibo, Venezuela
* Author to whom correspondence should be addressed.
Received: 3 June 2004 / Revised: 15 August 2004 / Accepted: 16 August 2004 / Published: 30 September 2004
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Abstract

We report high quality B3LYP Ab Initio studies of the electric dipole polarizability of three related series of molecules: para-XC6H4Y, XC6H4CH=CHC6H4Y and XC6H4N=NC6H4Y, where X and Y represent H together with the six various activating through deactivating groups NH2, OH, OCH3, CHO, CN and NO2. Molecules for which X is activating and Y deactivating all show an enhancement to the mean polarizability compared to the unsubstituted molecule, in accord with the order given above. A number of representative Ab Initio calculations at different levels of theory are discussed for azoarene; all subsequent Ab Initio polarizability calculations were done at the B3LYP/6-311G(2d,1p)//B3LYP/6-311++G(2d,1p) level of theory. We also consider semi-empirical polarizability and molecular volume calculations at the AM1 level of theory together with QSAR-quality empirical polarizability calculations using Miller’s scheme. Least-squares correlations between the various sets of results show that these less costly procedures are reliable predictors of for the first series of molecules, but less reliable for the larger molecules.
Keywords: Ab Initio; Miller indices; AM1; dipole polarizability; QSAR; Stilbene; azoarene; push-pull mechanism Ab Initio; Miller indices; AM1; dipole polarizability; QSAR; Stilbene; azoarene; push-pull mechanism
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Hinchliffe, A.; Nikolaidi, B.; Soscún Machado, H.J. Density Functional Studies of the Dipole Polarizabilities of Substituted Stilbene, Azoarene and Related Push-Pull Molecules. Int. J. Mol. Sci. 2004, 5, 224-238.

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