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Issue 23, 2010
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Binary complexes of tertiary amines with phenylacetylene. Dispersion wins over electrostatics

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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.

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

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Publication details

The article was received on 03 Sep 2009, accepted on 24 Feb 2010 and first published on 13 Apr 2010


Article type: Paper
DOI: 10.1039/B918013C
Citation: Phys. Chem. Chem. Phys., 2010,12, 6150-6156
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    Binary complexes of tertiary amines with phenylacetylene. Dispersion wins over electrostatics

    S. Maity, G. N. Patwari, S. Karthikeyan and K. S. Kim, Phys. Chem. Chem. Phys., 2010, 12, 6150
    DOI: 10.1039/B918013C

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