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Hydrogen‐bonding interactions of the trifluoromethyl group: 2‐Trifluoromethylvinyl alcohol
Author(s) -
Kovács Attila,
Hargittai István
Publication year - 1997
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/(sici)1097-461x(1997)62:6<645::aid-qua7>3.0.co;2-w
Subject(s) - isodesmic reaction , intramolecular force , chemistry , hydrogen bond , molecule , bond length , ab initio , computational chemistry , trifluoromethyl , alcohol , single bond , crystallography , halogen bond , group (periodic table) , density functional theory , stereochemistry , organic chemistry , alkyl
As part of our investigation of intramolecular hydrogen bonding and its geometrical consequences, ab initio molecular orbital calculations on 2‐trifluoromethylphenol and 2‐trifluoromethylvinyl alcohol and their parent structures were performed at the MP2/6–31+G ** level of theory. The intramolecular hydrogen bonding in 2‐trifluoromethylvinyl alcohol appears stronger than that in 2‐trifluoromethylphenol as witnessed by the shorter F...H interaction (1.96 Å) and the greater bond length changes in the rest of the molecule, as compared with the respective parent molecules. Beyond the geometrical characteristics, the energetics of hypothetical isodesmic reactions and the small shift of the O(SINGLE BOND)H stretching frequency indicate that these C(SINGLE BOND)F...H(SINGLE BOND)O interactions are rather weak. © 1997 John Wiley & Sons, Inc. Int J Quant Chem 62: 645–652, 1997