Binary complexes of tertiary amines with phenylacetylene. Dispersion wins over electrostatics

Literature Information

Publication Date 2010-04-13
DOI 10.1039/B918013C
Impact Factor 3.676
Authors

Surajit Maity, G. Naresh Patwari, S. Karthikeyan, Kwang S. Kim


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Abstract

The structures of the binary complexes between phenylacetylene and several tertiary amines viz., triethylamine, 1-ethylpiperidine, 1-ethylpiperazine, 1-azabicyclo[2.2.2]octane, and 1,4-diazabicyclo[2.2.2]octane were inferred using infrared-optical double resonance spectroscopy. The IR spectra in the acetylenic C–H stretching region clearly rule out the formation of electrostatic dominated C–H⋯N hydrogen bonded complexes. The IR spectra also point to the fact that all the five tertiary amines interact with the extended π electron density of the phenylacetylene moiety, leading to the formation of multidentate C–H⋯π hydrogen bonded complexes. Additionally a very weak electrostatic C–H⋯N hydrogen bond enhances the stability of the complex marginally. The multidentate C–H⋯π hydrogen bonded complexes are stabilized by a substantial contribution from the dispersion energy.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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