A QSPR-Approach to the Estimation of the p K HB of Six-Membered Nitrogen-Heterocycles using Quantum Mechanically Derived Descriptors

1 April 2002

journal article
Published by Springer Nature in Journal of Molecular Modeling

Vol. 8 (4) , 95-101
https://doi.org/10.1007/s00894-002-0075-z

Abstract

Descriptors derived from semiempirical (AM1) molecular orbital calculations have been used to construct a quantitative structure-property relationship (QSPR) for the thermodynamic hydrogen-bond basicity, pK _HB, of a series of six-membered aromatic nitrogen-heterocycles. The resulting model uses four-descriptors (the Coulson charge on the nitrogen atom, the energy of the localized nitrogen lone-pair orbital, the p-orbital contribution to this MO and an accessibility angle). The model gives r² _cv=0.95 for 51 compounds with a standard deviation between calculation and experiment of 0.13 log units.

Keywords

KEYWORDS. PKHB– HYDROGEN BONDING – QSPR – AM1

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