Issue 14, 2015

The propargylbenzene dimer: C–H⋯π assisted π–π stacking

Abstract

The propargylbenzene dimer was investigated using mass selected electronic and infrared spectroscopy in combination with quantum chemical calculations. The IR spectrum in the acetylenic C–H stretching region indicates that the two propargylbenzene units in the dimer are in an almost identical environment. The stabilization energies calculated at various levels of theory predict that the anti-parallel structure is the most stable isomer. The observed spectra are assigned to π-stacked structures which incorporate C–H⋯π interaction. The symmetry-adapted perturbation theory (SAPT) based energy decomposition analysis reveals that electrostatics contributes around 35% while the rest is due to dispersion. Comparison with the phenylacetylene and toluene dimers indicates that the higher stabilization energy of the PrBz dimer can be attributed to the synergy between the π–π stacking and C–H⋯π interactions.

Graphical abstract: The propargylbenzene dimer: C–H⋯π assisted π–π stacking

Supplementary files

Article information

Article type
Paper
Submitted
12 Jan 2015
Accepted
06 Feb 2015
First published
09 Feb 2015

Phys. Chem. Chem. Phys., 2015,17, 9090-9097

Author version available

The propargylbenzene dimer: C–H⋯π assisted π–π stacking

A. Kundu, S. Sen and G. N. Patwari, Phys. Chem. Chem. Phys., 2015, 17, 9090 DOI: 10.1039/C5CP00162E

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