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Title: Saturated hydrocarbon-benzene complexes: Theoretical study of cooperative CH/π interactions
Authors: Ran, J.
Wong, M.W. 
Issue Date: 10-Aug-2006
Citation: Ran, J., Wong, M.W. (2006-08-10). Saturated hydrocarbon-benzene complexes: Theoretical study of cooperative CH/π interactions. Journal of Physical Chemistry A 110 (31) : 9702-9709. ScholarBank@NUS Repository.
Abstract: High-level ab initio calculations at the CCSD(T)/aug-cc-pVTZ//MP2/aug(d,p)- 6-311G(d,p) level were employed to investigate the cooperative CH/π effects between the π face of benzene and several modeled saturated hydrocarbons, propane, isobutane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopentane, cyclooctane, and bicyclo[2.2.2]octane. In all cases, multiple C-H groups (2-4) are found to interact with the π face of benzene, with one C-H group pointing close to the center of the benzene ring. The geometries of these complexes are governed predominantly by electrostatic interaction between the interacting systems. The calculated interaction energies (10-14 kJ mol -1) are 2-3 times larger than that of the prototypical methane-benzene complex. The trends of geometries, interaction energies, binding properties, as well as electron-density topological properties were analyzed. The calculated interaction energies correlate well with the polarizabilities of the hydrocarbons. AIM analysis confirms the hydrogen-bonded nature of the CH/π interactions. Significant changes in proton chemical shift and stretching frequency (blue shift) are predicted for the ring C-H bond in these complexes. © 2006 American Chemical Society.
Source Title: Journal of Physical Chemistry A
ISSN: 10895639
DOI: 10.1021/jp0555403
Appears in Collections:Staff Publications

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