Solvatochromism of Heteroaromatic Compounds: XXV. Effect of Bifurcate Hydrogen Bond with a Weak Intramolecular Component on the IR,NMR, and UV Spectra of 2,6-Dibromo-4-nitrophenol |
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| Authors: | S. V. Fedorov I. G. Krivoruchka A. M. Shulunova L. V. Sherstyannikova O. M. Trofimova A. I. Vokin V. K. Turchaninov |
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| Affiliation: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russia |
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| Abstract: | Dissolution of 2,6-dibromo-4-nitrophenol in aprotic protophilic solvents forms a three-center solvation H-complex with a sharply weakened intramolecular hydrogen bond. This weakening is associated with a deformation of the bond angle of the hydroxy group. It is only on interaction with weak π-bases that the intramolecular component of the bifurcate hydrogen bond appreciably affects the spectral position of the OH stretching vibration band; this results in a nonlinear dependence between  OH and the Kamlet-Taft sol-vatochromic parameter.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 1, 2005, pp. 111–122.Original Russian Text Copyright © 2005 by Fedorov, Krivoruchka, Shulunova, Sherstyannikova, Trofimova, Vokin, Turchaninov. |
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