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Phenylacetylene: A Hydrogen Bonding Chameleon

Authors

  • Surajit Maity,

    1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076 (India), Fax: (+91) 22 2576 7152
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  • Mridula Guin,

    1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076 (India), Fax: (+91) 22 2576 7152
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  • Dr. Prashant Chandra Singh,

    1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076 (India), Fax: (+91) 22 2576 7152
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  • Prof. G. Naresh Patwari

    Corresponding author
    1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076 (India), Fax: (+91) 22 2576 7152
    • Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076 (India), Fax: (+91) 22 2576 7152
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Abstract

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.

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