Structural Chemistry

, Volume 24, Issue 2, pp 507–515

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

Authors

    • College of ScienceChina University of Petroleum (East China)
  • Jin Lin
    • College of Chemical EngineeringChina University of Petroleum (East China)
  • Zhanqing Qu
    • College of Petroleum EngineeringChina University of Petroleum (East China)
Original Research

DOI: 10.1007/s11224-012-0106-z

Cite this article as:
Lü, R., Lin, J. & Qu, Z. Struct Chem (2013) 24: 507. doi:10.1007/s11224-012-0106-z

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].

Keywords

ThiopheneDibenzothiopheneDensity functional theoryIonic liquids

Supplementary material

11224_2012_106_MOESM1_ESM.doc (7.8 mb)
Supplementary material 1 (DOC 8035 kb)

Copyright information

© Springer Science+Business Media, LLC 2012