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Organic Fluorine Hardly Ever Accepts Hydrogen Bonds
Author(s) -
Dunitz Jack D.,
Taylor Robin
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970030115
Subject(s) - covalent bond , hydrogen bond , fluorine , intermolecular force , ab initio , acceptor , chemistry , hydrogen , molecular orbital , chemical bond , computational chemistry , chemical physics , crystallography , materials science , molecule , organic chemistry , physics , condensed matter physics
Statistical analysis of structural data and detailed inspection of individual crystal structures culled from the Cambridge Structural Database and the Brookhaven Protein Data Bank show that covalently bound fluorine (in contrast to anionic fluoride) hardly ever acts as a hydrogen‐bond acceptor. The weakness of covalently bound fluorine as hydrogen‐bond acceptor is backed by results of new molecular orbital calculations on model systems using ab initio intermolecular perturbation theory (IMPT), and is in accord with results of other physicochemical studies and with the physical properties of fluorinated organic compounds. Factors influencing the strength of hydrogen bonding in extended systems are discussed.