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Experimental and Theoretical Evidence of CH⋅⋅⋅O Hydrogen Bonding in Liquid 4‐Fluorobenzaldehyde
Author(s) -
RibeiroClaro Paulo J. A.,
Marques M. Paula M.,
Amado Ana M.
Publication year - 2002
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/1439-7641(20020715)3:7<599::aid-cphc599>3.0.co;2-7
Subject(s) - hydrogen bond , chemistry , ab initio , chemical bond , hydrogen , ab initio quantum chemistry methods , computational chemistry , crystallography , molecule , organic chemistry
The presence of CH⋅⋅⋅O hydrogen bonds in liquid 4‐fluorobenzaldehyde has been studied by a combination of theoretical and spectroscopic methods. Ab initio calculations yielded bond energies and preferred bonding geometries, and the calculated spectroscopic properties have been compared with the experimental results. The presence of CH⋅⋅⋅O hydrogen bonds in the liquid phase is strongly supported by vibrational and NMR spectroscopic data. Particular attention is paid to the spectroscopic effects related to the predicted shortening of the CH bond engaged in the CH⋅⋅⋅O contact. The concentration‐dependent intensity in the CH stretching region is tentatively assigned to a blue‐shift effect due to CH⋅⋅⋅O hydrogen bonding.