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Role of Hydrogen Bond in the Solvation Behavior of the Binary Mixtures Containing Fluorocarbon Alcohol Molecules and Chloroform: An Experimental and Theoretical Study
Author(s) -
Biswas Biswajit,
Mondal Saptarsi,
Singh Prashant C.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601118
Subject(s) - solvation , chemistry , fluorocarbon , hydrogen bond , solvatochromism , chloroform , molecule , solvent , hydrogen , photochemistry , organic chemistry
Fluorocarbon containing alcohol molecules are important due to their unusual but important physicochemical properties. We have investigated solvatochromic as well as hydrogen bond behavior of weakly interacting binary mixtures of chloroform (CHCl 3 ) with the fluorocarbon containing alcohols namely, 2‐fluoroethanol (MFE) and 2,2,2‐trifluoroethanol (TFE) as well as compared them with ethanol (ETH)‐CHCl 3 binary mixture. UV‐Vis study depicts that the particular composition (χ ETH ∼0.6) of the binary mixtures of CHCl 3 with ETH and MFE solvate probes more efficiently as compared to the respective counterparts, whereas, the probes are preferably solvated by the TFE as compared to solvent mixtures in the case of TFE‐CHCl 3 binary mixture. NMR, IR as well as theoretical calculations establish that CHCl 3 forms the C−H…O hydrogen bonded clusters with ETH and MFE whereas TFE‐CHCl 3 binary mixture are connected predominantly through C−H…F hydrogen bond. The dipole of probe molecules perturbs the weaker C−H…F hydrogen bond present in the TFE‐CHCl 3 binary mixture resulting in the preferential solvation by the TFE, whereas, the comparatively stronger C−H…O hydrogen bonded species is preserved in the binary mixtures of CHCl 3 with ETH and MFE which leads to the favorable solvation by the binary mixtures of CHCl 3 with ETH and MFE. Further, analytical solvent exchange models have been used to substantiate the solvation behavior of the probe molecules in the CHCl 3 binary mixtures with ETH and TFE.