Premium
Phenylacetylene: A Hydrogen Bonding Chameleon
Author(s) -
Maity Surajit,
Guin Mridula,
Singh Prashant Chandra,
Patwari G. Naresh
Publication year - 2011
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/cphc.201000630
Subject(s) - phenylacetylene , intermolecular force , hydrogen bond , lone pair , chemistry , chemical physics , molecule , computational chemistry , ab initio , non covalent interactions , ab initio quantum chemistry methods , organic chemistry , catalysis
Molecules with multiple hydrogen bonding sites offer the opportunity to investigate competitive hydrogen bonding. Such an investigation can become quite interesting, particularly when the molecule of interest has neither lone‐pair electrons nor strongly acidic/basic groups. Phenylacetylene is one such molecule with three hydrogen bonding sites that cannot be ranked into any known hierarchical pattern. Herein we review the structures of several binary complexes of phenylacetylene investigated using infrared optical double‐resonance spectroscopy in combination with high‐level ab initio methods. The diversity of intermolecular structures formed by phenylacetylene with various reagents is remarkable. The nature of intermolecular interaction with various reagents is the result of a subtle balance between various configurations and competition between the electrostatic and dispersion energy terms, while trying to maximize the total interaction strength.