By Reece H Vallance

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The same computational experiment can be made with the analogous septuplet state of benzene, whose distortion energy is about three times that of quadruplet allyl, and is now much larger than the ground state's resistance to distortion (see Table 1). This means that the geometries of allyl and benzene are governed by two opposing driving forces: the cr bonds which favor a symmetric geometry with equal bond lengths, and the n bonds which favor a Kekulran alternated geometry. The latter driving force is rather weak in the case of allyl, and stronger in benzene, but in both cases it is outweighed by the c driving force and a symmetrical geometry results, not because but in spite of the rc electrons.

72:650 13. Bishop DM (1973) Group Theory and Chemistry, Clarendon, Oxford, p 204 14. McKelvey JM, Berthier G (1976) Chem. Phys. Lett. 41:476 15. (a) Huron B, Malrieu J-P, Rancurel P (1973) J. Chem. Phys. 58: 5745; (b) Malrieu J-P (1982) Theor. Chim. Acta 62: 163; (c) Evangelisti S, Daudey J-P, Malrieu J-P (1983) Chem. Phys. 75:91 t6. Coulson CA, Altman S L (1952) Trans. Faraday Soc. 48:293 17. (a) Dewar MJS, de Llano C (1969) J. Amer. Chem. Soc. 91: 789; (b) Dewar MJS, Gleicher GJ (1965) J. Amer.

Li2). According to this theory, the n systems of aromatic hydrocarbons are expected to be unstable in a regular geometry and to be more stable in an alternated one. To verify this prediction, the driving force responsible for the regular geometry of aromatic rc systems is analyzed by means of rigorous ab initio calculations, and decomposed into its rc and cr components. The same decomposition is performed for antiaromatic systems. While the cr driving force is, by nature, always symmetrizing, it is shown that the ~ driving force of a variety of x systems (C6H6, N 6, P6, Si6H6, C4H4, N4, Si4H4, P4) is always distortive, and that the rc propensity to distort is proportional to the strength of the 2e-rt bond, as predicted by the Valence Bond model.

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A textbook of inorganic chemistry vol.VI part IV Arsenic by Reece H Vallance


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