Abstract
Within the calculation at the MP2/6-311++G(d,p) level and QTAIM analysis the structural investigation of 2,6-bis-[2-(1H-pyrrole-2-yl)-vinyl]-pyridine and 2,5-bis-[2-(pyridine-2-yl)-vinyl]-1H-pyrrole is performed. It is found that a symmetric three-centered hydrogen bond forms in the first molecule. The components of this bond are substantially weakened in comparison with the two-centered hydrogen bond in the Z-isomer of 2-[2-(1H-pyrrole-2-yl)-vinyl]-pyridine. This weakening is due to the steric interaction of two hydrogen bond donors. At the same time, more rigid steric conditions for the formation of a three-centered interaction in 2,5-bis-[2-(pyridine-2-yl)-vinyl]-1H-pyrrole results in actual dissociation of one of the components of the three-center hydrogen bond accompanied by the strengthening of the retained component. This provides the possibility of rocking vibrations of the hydrogen bond in the latter case due to the alternate entrance of hydrogen bond acceptors into the coordination sphere of the hydrogen atom.
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Original Russian Text Copyright © 2013 by A. V. Vashchenko, A. V. Afonin
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Translated from Zhurnal Strukturnoi Khimii, Vol. 54, No. 4, pp. 605–614, July–August, 2013.
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Vashchenko, A.V., Afonin, A.V. Features of three-centered hydrogen bonding in di(vinylpyrrolyl)pyridine and di(vinylpyridyl)-pyrrole from the ab initio calculation data and QTAIM analysis. J Struct Chem 54, 651–659 (2013). https://doi.org/10.1134/S002247661304001X
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DOI: https://doi.org/10.1134/S002247661304001X