Original Research

Structural Chemistry

, Volume 20, Issue 1, pp 37-41

Novel type of mixed O–H···N/O–H···π hydrogen bonds: monohydrate of pyridine

  • Oleg V. ShishkinAffiliated withSSI “Institute for Single Crystals”, National Academy of Science of UkraineUkrainian-American Laboratory of Computational ChemistryV.N. Karazin Kharkiv National University Email author 
  • , Irina S. KonovalovaAffiliated withSSI “Institute for Single Crystals”, National Academy of Science of UkraineUkrainian-American Laboratory of Computational Chemistry
  • , Leonid GorbAffiliated withUkrainian-American Laboratory of Computational ChemistryInterdisciplinary Nanotoxicity Center, Department of Chemistry, Jackson State UniversityDepartment of Molecular Biophysics, Institute of Molecular Biology and Genetics, National Academy of Science of Ukraine
  • , Jerzy LeszczynskiAffiliated withUkrainian-American Laboratory of Computational ChemistryInterdisciplinary Nanotoxicity Center, Department of Chemistry, Jackson State University

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Abstract

Investigation of characteristics of hydrogen bonding between pyridine and water by MP2/aug-cc-pvdz method reveals that these two molecules may form three types of hydrogen bonds depending on nature of proton withdrawal site of pyridine. Change of orientation of water with respect to plane of aromatic ring leads to transformation of the O–H···N bond to O–H···π bond via wide region of the potential energy surface where both lone pair of the nitrogen atom and π-system make significant contribution into hydrogen bonding. Hydrogen bond in this intermediate region may be considered as mixed O–H···N/O–H···π bond representing new type of H bonds.

Keywords

Hydrogen bonding π-system Pyridine monohydrate