Charge calculations in molecular mechanics IV: A general method for conjugated systems

Journal of Computational Chemistry - Tập 9 Số 4 - Trang 288-297 - 1988
Raymond J. Abraham1, Paul E. Smith1
1The School of Chemistry, University of Liverpool, Liverpool L69 3BX, England

Tóm tắt

AbstractA general method for calculating pi charges based on the Hückel molecular orbital (HMO) approach is incorporated into an existing scheme for calculating partial atomic charges in saturated systems. The parametrization of the Hückel coulomb and resonance integrals is given based on (a) the CNDO pi densities and (b) the observed molecular dipole moments. The results for these two schemes are compared both with other theoretical methods and also with the observed dipole moments of a variety of conjugated and aromatic compounds. The dipole moment (DM) parametrization gives in general more consistent results and is to be preferred. The compounds studied include substituted olefins and aromatics (with substituents R, F, Cl, Br, I, OR), aldehydes, ketones, acids, esters, amides, and the heterocyclic ring systems of furan, pyrrole, pyridine, and indole.

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Tài liệu tham khảo

10.1002/jcc.540030316

10.1002/jcc.540050609

10.1002/jcc.540060304

10.1016/0040-4020(80)80168-2

10.1002/anie.198506871

Greenwood H. H., 1972, Computing Methods in Quantum Organic Chemistry

Streitwieser A., 1961, Molecular Orbital Theory for Organic Chemists

Dewar M. J. S., 1969, The Molecular Orbital Theory of Organic Chemistry

Heilbronner E., 1976, The HMO Model

10.1002/bip.360100707

10.1021/jo01311a060

McClellan A. L., 1963, Tables of Experimental Dipole Moments

1974, Tables of Experimental Dipole Moments

CNDO/2 QCPE PROGRAM 91 G. A.Segal(1966).

Pauling L., 1960, The Nature of the Chemical Bond

10.1021/ar50030a003

10.1139/v86-500

10.1016/S0065-3160(08)60341-X

10.1021/ja00993a001

10.1021/ja00523a008

10.1063/1.1711841

10.1021/ja00863a008

10.1021/ja00518a014

10.1021/ja00798a002

Hellwege K. H., 1976, Structure Data of Free Polyatomic Molecules

10.1063/1.1733575

10.1063/1.1731582

10.1246/bcsj.52.2451

10.3891/acta.chem.scand.23-2848

10.1016/0040-4020(80)80016-0

10.1016/0040-4020(82)80235-4

10.1007/978-1-4684-1770-8

10.1039/f29797500302

10.1063/1.1700891

10.3891/acta.chem.scand.21-1415

10.1016/0022-2860(71)90008-1

Carl R. F., 1959, J. Chem. Phys., 30, 1529, 10.1063/1.1730232

10.1039/tf9716700950

10.1016/0009-2614(76)80638-0

10.1063/1.1668886

Davis M. J., 1965, J. Chem. Phys., 69, 4091, 10.1021/j100782a007

10.3891/acta.chem.scand.32a-0271

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Thông tin xuất bản

Journal of Computational Chemistry

Tập 9 Số 4

288-297

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