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Related Experiment Videos

Phenylacetylene: a hydrogen bonding chameleon.

Surajit Maity1, Mridula Guin, Prashant Chandra Singh

  • 1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|January 13, 2011
PubMed
Summary

Phenylacetylene, a molecule lacking typical bonding groups, exhibits complex hydrogen bonding. Its diverse intermolecular structures reveal a delicate balance of electrostatic and dispersion forces.

Related Experiment Videos

Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Molecules with multiple hydrogen bonding sites enable competitive hydrogen bonding studies.
  • Phenylacetylene presents a unique case with three hydrogen bonding sites lacking lone-pair electrons or strongly acidic/basic groups.
  • Existing hierarchical patterns do not apply to phenylacetylene's hydrogen bonding sites.

Purpose of the Study:

  • To investigate the competitive hydrogen bonding of phenylacetylene.
  • To analyze the intermolecular structures formed by phenylacetylene with various reagents.
  • To understand the factors governing the diverse intermolecular interactions of phenylacetylene.

Main Methods:

  • Infrared optical double-resonance spectroscopy was employed.
  • High-level ab initio computational methods were utilized.
  • Binary complexes of phenylacetylene were structurally investigated.

Main Results:

  • Phenylacetylene forms a remarkable diversity of intermolecular structures with different reagents.
  • The observed structures result from a subtle balance between various configurations.
  • Competition between electrostatic and dispersion energy terms influences the interaction strength.

Conclusions:

  • Phenylacetylene's hydrogen bonding behavior is complex and not easily categorized.
  • Intermolecular interactions are governed by a delicate interplay of forces.
  • The study highlights the unique nature of phenylacetylene in hydrogen bonding research.