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

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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.

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Received: 25 October 2001 / Accepted: 7 February 2002 / Published online: 11 April 2002

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Hennemann, M., Clark, T. A QSPR-Approach to the Estimation of the pK HB of Six-Membered Nitrogen-Heterocycles using Quantum Mechanically Derived Descriptors. J Mol Model 8, 95–101 (2002). https://doi.org/10.1007/s00894-002-0075-z

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  • DOI: https://doi.org/10.1007/s00894-002-0075-z

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