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Charge calculations in molecular mechanics 7: Application to polar π systems incorporating nitro, cyano, amino, C=S and thio substituents

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Summary

A previously described method for calculating partial atomic charges in molecules has been applied to a variety of different functional groups withπ electrons. Theπ charges have been determined by varying the relevant Hückel coulombic and resonance integrals so as to reproduce the experimental dipole moments of known compounds. These include nitro, cyano, mercapto and thiocarbonyl compounds, anilines and a series of heterocyclic ring compounds involving nitrogen, oxygen and sulphur atoms. The calculated dipole moments are in good agreement with experimental values and are a considerable improvement on other calculated values, while requiring only a fraction of the computational time necessary for more rigorous methods. The resultingπ densities compare favourably with other theoretical (CNDO, MNDO and STO-3G) methods.

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Authors and Affiliations

  1. Robert Robinson Laboratories, University of Liverpool, L69 3BX, Liverpool, UK

    Raymond J. Abraham & Paul E. Smith

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  1. Raymond J. Abraham
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  2. Paul E. Smith
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For part 6, see Ref. 7.

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Abraham, R.J., Smith, P.E. Charge calculations in molecular mechanics 7: Application to polar π systems incorporating nitro, cyano, amino, C=S and thio substituents. J Computer-Aided Mol Des 3, 175–187 (1989). https://doi.org/10.1007/BF01557727

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  • DOI: https://doi.org/10.1007/BF01557727

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