Quantification of intramolecular nonbonding interactions in organochalcogens

The Journal of Physical Chemistry. a
Dipankar Roy, Raghavan B Sunoj

Abstract

Intramolecular nonbonding interactions between chalcogen atoms in a series of ortho substituted arylselenides (S/O...Se-Y, with Y = -Me, -CN, -Cl, and -F) are quantified using the coupled cluster CCSD(T)/cc-pVDZ level of theory. A homodesmic reaction method as well as an ortho-para approach are employed in evaluating the strength of intramolecular interactions. Comparison of the results obtained using the ab initio MP2 method and pure and hybrid density functional theories are performed with that of the coupled cluster values to assess the quality of different density functionals in evaluating the strength of nonbonding interactions. The interaction energies are found to be higher when the thioformyl group acts as the donor and the Se-F bond acts as the acceptor. In a given series with the same donor atom, the strength of the interaction follows the order Me < CN < Cl < F, exhibiting fairly high sensitivity to the group attached to selenium (Se-Y). Analysis of electron density at the S/O...Se bond critical point within the Atoms in Molecule framework shows a very good correlation with the computed intramolecular interaction energies.

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Citations

Jun 19, 2013·Journal of Chemical Information and Modeling·Mirosław Jabłoński, Guglielmo Monaco
Aug 19, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·K SelvakumarRay J Butcher
Jul 3, 2015·The Journal of Organic Chemistry·Vijay P SinghLars Engman
Jun 9, 2015·Physical Chemistry Chemical Physics : PCCP·Marlena ŁukomskaMarcin Palusiak
Oct 23, 2009·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Bani Kanta Sarma, Govindasamy Mugesh
Jan 3, 2013·Angewandte Chemie·Tullimilli Y GopalakrishnaVenkataramanarao G Anand
Oct 13, 2018·Chemical Science·Karuthapandi Selvakumar, Harkesh B Singh
Dec 2, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mirosław Jabłoński
Apr 14, 2010·Chemical Reviews·Anna J MukherjeeRaghavan B Sunoj
Mar 18, 2008·The Journal of Physical Chemistry. a·A F LagoJ-L M Abboud
Aug 30, 2008·The Journal of Physical Chemistry. a·Dipankar RoyRaghavan B Sunoj
Nov 10, 2006·The Journal of Physical Chemistry. a·Milind M DeshmukhLibero J Bartolotti
Dec 19, 2007·The Journal of Physical Chemistry. a·Milind M DeshmukhShridhar R Gadre

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