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J Chem Inf Model. 2013 May 24;53(5):1191-9. doi: 10.1021/ci4001597. Epub 2013 May 13.

Characterization of biaryl torsional energetics and its treatment in OPLS all-atom force fields.

Author information

1
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States.

Abstract

The frequency of biaryl substructures in a database of approved oral drugs has been analyzed. This led to designation of 20 prototypical biaryls plus 10 arylpyridinones for parametrization in the OPLS all-atom force fields. Bond stretching, angle-bending, and torsional parameters were developed to reproduce the MP2 geometries and torsional energy profiles. The transferability of the new parameters was tested through their application to three additional biaryls. The torsional energetics for the 33 biaryl molecules are analyzed and factors leading to preferences for planar and nonplanar geometries are identified. For liquid biphenyl, the computed density and heat of vaporization at the boiling point (255 °C) are also reported.

PMID:
23621692
PMCID:
PMC3707137
DOI:
10.1021/ci4001597
[Indexed for MEDLINE]
Free PMC Article

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