Structural Chemistry

, Volume 24, Issue 2, pp 507–515 | Cite as

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

Original Research


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].


Thiophene Dibenzothiophene Density functional theory Ionic liquids 



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).

Supplementary material

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


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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  1. 1.College of ScienceChina University of Petroleum (East China)QingdaoChina
  2. 2.College of Chemical EngineeringChina University of Petroleum (East China)QingdaoChina
  3. 3.College of Petroleum EngineeringChina University of Petroleum (East China)QingdaoChina

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