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Theoretical study on interactions between thiophene/dibenzothiophene/cyclohexane/toluene and 1-methyl-3-octylimidazolium tetrafluoroborate

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Abstract

It is critically important to understand the interactions between thiophene/dibenzothiophene/cyclohexane/toluene and 1-methyl-3-octylimidazolium tetrafluoroborate ([C8MIM]+[BF4]−) due to desulfurization by ionic liquids. In this work, the structures of thiophene, dibenzothiophene, cyclohexane, toluene, [C8MIM]+[BF4]−, [C8MIM]+[BF4]−-thiophene, [C8MIM]+[BF4]−-dibenzothiophene, [C8MIM]+[BF4]−-cyclohexane, and [C8MIM]+[BF4]−-toluene were optimized systematically at the GGA/PW91/DNP level, and the most stable geometries were performed by NBO and AIM analyses. It was found that [BF4]− anion tends to locate near C2–H2 and four hydrogen bonds between [C8MIM]+ and [BF4]− form in [C8MIM]+[BF4]−. There exist hydrogen bonds and C–H···π interactions between [C8MIM]+[BF4]− and thiophene/cyclohexane/toluene, while the hydrogen bonding interactions, π···π and C–H···π interactions occur between [C8MIM]+[BF4]− and dibenzothiophene confirmed by NBO and AIM analyses. The interaction energies between [C8MIM]+[BF4]− and thiophene, dibenzothiophene, cyclohexane, toluene are 18.83, 20.93, 6.83, 12.99 kcal/mol, showing the preferential adsorption of dibenzothiophene and thiophene by ionic liquid, in agreement with the experimental results of dibenzothiophene and thiophene extraction by [C8MIM]+[BF4]−.

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Acknowledgments

The authors gratefully acknowledge financial support from the Important Project of Science and Technology in Developing Great Oil & Gas Field and Coal Bed Gas (2011ZX05051).

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Authors and Affiliations

  1. College of Science, China University of Petroleum (East China), Qingdao, 266580, Shandong, China

    Renqing Lü

  2. College of Chemical Engineering, China University of Petroleum (East China), Qingdao, 266580, Shandong, China

    Jin Lin

  3. College of Petroleum Engineering, China University of Petroleum (East China), Qingdao, 266580, Shandong, China

    Zhanqing Qu

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Correspondence to Renqing Lü.

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Lü, R., Lin, J. & Qu, Z. Theoretical study on interactions between thiophene/dibenzothiophene/cyclohexane/toluene and 1-methyl-3-octylimidazolium tetrafluoroborate. Struct Chem 24, 507–515 (2013). https://doi.org/10.1007/s11224-012-0106-z

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