| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1408574 | Journal of Molecular Structure | 2014 | 7 Pages |
•2-Iminium-1,3-dithiolane as a new family of ionic liquids were synthesized.•Theoretical study on the synthesized ionic liquids was also performed.•QTAIM analysis show that the hydrogen bonds are closed shell in the nature.•1H and 13C calculated chemical shifts were obtained for ionic liquids.
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 1H and 13C calculated chemical shifts at the B3LYP/6-311++G** level were in agreement with experimental chemical shifts for synthesized ionic liquids.
Graphical abstract2-Iminium-1,3-dithiolanes have been synthesized as a new family of ionic liquids theoretical study on the synthesized ionic liquids was also performed by quantum chemistry calculation.Figure optionsDownload full-size imageDownload as PowerPoint slide
