A. Halimehjani, Mehdi Shakourian-Fard, Marziye Vahdati Farvardin
Jan 6, 2014
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Influential Citations
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Journal
Journal of Molecular Structure
Abstract
Abstract An efficient method for synthesis of 2-iminium-1,3-dithiolane as a new family of ionic liquids with reaction of dithiocarbamates with methyl triflouromethanesulfonate was described. Theoretical study on the synthesized ionic liquids was also performed by quantum chemistry calculation. Geometry optimization on the ion pairs was carried out with the B3LYP/6-311++G(d,p) level of theory. The interaction energies were calculated, and corrected by the basis set superposition error (BSSE) calculated by the counterpoise method. The results of natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) analyses indicate that the interactions occur via hydrogen bonding between oxygen atom lone pairs (lp(O)) of triflouromethanesulfonate anion and antibonding orbitals of σ * C–H of 2-iminium-1,3-dithiolane cations. Also, the results of QTAIM analysis show that the hydrogen bonds are closed shell (electrostatic) in the nature. Finally, the 1 H and 13 C calculated chemical shifts at the B3LYP/6-311++G ** level were in agreement with experimental chemical shifts for synthesized ionic liquids.