Influence of Stacking on Hydrogen Bonding: Quantum Chemical Study on Pyridine−Benzene Model Complexes

Autor:	Pierre Mignon, Paul Geerlings, Stefan Loverix, Frank De Proft
Rok vydání:	2004
Předmět:	chemistry.chemical_compound chemistry Computational chemistry Hydrogen bond Ab initio quantum chemistry methods Pyridine Substituent Stacking Density functional theory Interaction energy Physical and Theoretical Chemistry Benzene
Zdroj:	The Journal of Physical Chemistry A. 108:6038-6044
ISSN:	1520-5215 1089-5639
Popis:	The present work focuses on the influence of aromatic stacking on the ability of an aromatic nitrogen base to accept a hydrogen bond. Substituent effects were studied at the MP2 level for 10 complexes of a substituted benzene stacked with pyridine in a parallel offset conformation. The interaction energies between each substituted benzene and pyridine were analyzed in terms of Hartree−Fock, correlation, and electrostatic contributions. It appears that the basicity of pyridine is directly related to the electrostatic interaction between the cycles. It increases with increasing electron donating character of the benzene substituents. Also, density functional theory based descriptors such as global and local hardnesses and the benzene ring polarizability are found to adequately predict the interaction energy. These findings may be important in the study of DNA/RNA chains.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8e2dde8b299a20e486da3b47de12e2ed https://doi.org/10.1021/jp049240h Zobrazit plný text záznamu