Molecular modeling annual

, Volume 8, Issue 4, pp 95–101

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

  • Matthias Hennemann
  • Timothy Clark
Original Paper

DOI: 10.1007/s00894-002-0075-z

Cite this article as:
Hennemann, M. & Clark, T. J Mol Model (2002) 8: 95. doi:10.1007/s00894-002-0075-z


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, pKHB, 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 r2cv=0.95 for 51 compounds with a standard deviation between calculation and experiment of 0.13 log units.

Keywords. pKHB– Hydrogen bonding – QSPR – AM1

Copyright information

© Springer-Verlag 2002

Authors and Affiliations

  • Matthias Hennemann
    • 1
  • Timothy Clark
    • 1
  1. 1.Computer-Chemie-Centrum der Friedrich-Alexander-Universität Erlangen-Nürnberg, Nägelsbachstraße 25, 91054 Erlangen, Germany. E-mail: Phone: +49-9131-8522948 Fax: +49-9131-8526565DE