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COSMIC(90): An improved molecular mechanics treatment of hydrocarbons and conjugated systems

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Summary

Four modifications to the COSMIC molecular mechanics force field are described, which greatly increase both its versatility and the accuracy of calculated conformational energies. The Hill non-bonded van der Waals potential function has been replaced by a two-parameter Morse curve and a new H-H potential, similar to that in MM3, incorporated. Hydrocarbon energies in particular are much improved.

A simple iterative Hückel pi-electron molecular orbital calculation allows modelling of conjugated systems. Calculated bond lengths and rotational barriers for a series of conjugated hydrocarbons and nitrogen heterocycles are shown to be as accurate as those determined by the MM2 SCF method.

Explicit hydrogen-bonding potentials for H-bond acceptor-donor atom pairs have been included to give better hydrogen bond energies and lengths. The van der Waals radii of protonic hydrogens are reduced to 0.5 Å and the energy well depth is increased to 1.0 kcal mol-1.

Two new general atom types, N+ 2sp and O- 3sp , have been introduced which allow a wide variety of charged conjugated systems to be studied. A minimum of parameterisation is required, as the new types are easily included in the Hückel scheme which automatically adjusts bond and torsional parameters according to the defined bond-order relationships.

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Author notes

  1. Jeremy G. Vinter

    Present address: Department of Chemistry, University College London, WC1H 0AJ, London, U.K.

Authors and Affiliations

  1. Department of Pharmaceutical Sciences, University of Nottingham, University Park, NG7 2RD, Nottingham, U.K.

    S. David Morley & David E. Jackson

  2. The School of Chemistry, The University of Liverpool, P.O. Box 147, L69 3BX, Liverpool, U.K.

    Raymond J. Abraham

  3. Oxford Centre for Molecular Sciences and Physical Chemistry, Oxford University, South Parks Road, OX1 3QZ, Oxford, U.K.

    Ian S. Haworth

  4. SmithKline Beecham Pharmaceuticals, The Frythe, AL6 9AR, Welwyn, Herts, U.K.

    Martin R. Saunders

  5. Baylay's Glen, Fore Street, Weston, SG4 7AS, Hitchin, Herts, U.K.

    Jeremy G. Vinter

  6. University Chemical Laboratories, University of Cambridge, CB2 1EW, Cambridge, U.K.

    Jeremy G. Vinter

Authors
  1. S. David Morley
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  2. Raymond J. Abraham
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  4. David E. Jackson
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  5. Martin R. Saunders
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  6. Jeremy G. Vinter
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Morley, S.D., Abraham, R.J., Haworth, I.S. et al. COSMIC(90): An improved molecular mechanics treatment of hydrocarbons and conjugated systems. J Computer-Aided Mol Des 5, 475–496 (1991). https://doi.org/10.1007/BF00125666

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  • DOI: https://doi.org/10.1007/BF00125666

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