Theoretical Studies on Interaction Between CO2 Gas and Imidazolium-Type Organic Ionic Liquid Using DFT and Natural Bond Orbital Calculations

Saied M. Soliman

doi:10.14233/ajchem.2016.19262

Issue

Vol. 28 No. 1 (2016): Vol 28 Issue 1

Issue Published : October 5, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Theoretical Studies on Interaction Between CO2 Gas and Imidazolium-Type Organic Ionic Liquid Using DFT and Natural Bond Orbital Calculations

https://doi.org/10.14233/ajchem.2016.19262

Saied M. Soliman

Department of Chemistry, Rabigh College of Science and Art, King Abdulaziz University, Jeddah, P.O. Box 344, Rabigh 21911, Saudi Arabia; Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426 Ibrahimia, 21525 Alexandria, Egypt

Corresponding Author(s) : Saied M. Soliman

ssoleman@kau.edu.sa; saied1soliman@yahoo.com

Asian Journal of Chemistry, Vol. 28 No. 1 (2016): Vol 28 Issue 1
Article Published : October 6, 2015

Abstract

The interaction between 4,5-dibromo-1-butyl-3-methylimidazolium trifluoromethanesulfonate; [DBBIM][TFMSO₃] ionic liquid and CO₂ gas has been studied using DFT calculations. With the help of natural bond orbital (NBO) analyses, the second order perturbation energies of the most interacting natural bond orbitals and natural atomic charges have been predicted by the density functional theory (DFT) computations at the X3LYP/6-31++G(d,p) level of theory. The natural charge calculations showed that in the ionic liquid-CO₂ system, the [DBBIM][TFMSO₃] ionic liquid is the electron donor while CO₂ gas is an electron acceptor. Further stabilization of the imidazolium ring p-system is produced due to the interaction of the CO₂ gas with the ionic liquid. The polarization of the C–O and S1–O3 bonds are affected significantly by such interactions. The charge decomposition (CDA) analysis revealed the strong interactions between the [DBBIM]⁺ and [TFMSO₃]^– ions of the ionic liquid and the weak interaction between the ionic liquid and the CO₂ gas. The mp2 interaction energy of ionic liquid-CO₂ system is only 3.6107 kcal/mol.

Keywords

Ionic liquid Charge transfer Natural bond orbital analysis DFT/X3LYP Charge

Soliman, S. M. (2015). Theoretical Studies on Interaction Between CO2 Gas and Imidazolium-Type Organic Ionic Liquid Using DFT and Natural Bond Orbital Calculations. Asian Journal of Chemistry, 28(1), 116–120. https://doi.org/10.14233/ajchem.2016.19262

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References

D.M. D'Alessandro, B. Smit and J.R. Long, Angew. Chem. Int. Ed., 49, 6058 (2010); doi:10.1002/anie.201000431.
E.D. Bates, R.D. Mayton, I. Ntai and J.H. Davis, J. Am. Chem. Soc., 124, 926 (2002); doi:10.1021/ja017593d.
C.Y. Hong, C.Y. Fei, D.D. Shun, A. Ning and Z. Yong, J. Mol. Liq., 199, 7 (2014); doi:10.1016/j.molliq.2014.06.023.
F. Jensen, Introduction to Computational Chemistry, Wiley & Sons, Chichester, Chp. 9 (1999).
R.S. Mulliken, J. Chem. Phys., 23, 1833 (1955); doi:10.1063/1.1740588.
U.C. Singh and P.A. Kollman, J. Comput. Chem., 5, 129 (1984); doi:10.1002/jcc.540050204.
A.J. Stone and M. Alderton, Mol. Phys., 56, 1047 (1985); doi:10.1080/00268978500102891.
L.E. Chirlian and M.M. Francl, J. Comput. Chem., 8, 894 (1987); doi:10.1002/jcc.540080616.
C.M. Breneman and K.B. Wiberg, J. Comput. Chem., 11, 361 (1990); doi:10.1002/jcc.540110311.
D.E. Williams, Rev. Comput. Chem., 2, 219 (1991); doi:10.1002/9780470125793.ch6.
C.A. Reynolds, J.W. Essex and W.G. Richards, J. Am. Chem. Soc., 114, 9075 (1992); doi:10.1021/ja00049a045.
C. Aleman, M. Orozro and F.J. Luque, Chem. Phys., 189, 573 (1994); doi:10.1016/0301-0104(94)00310-6.
U. Koch and E. Egert, J. Comput. Chem., 16, 937 (1995); doi:10.1002/jcc.540160803.
D.S. Marynick, J. Comput. Chem., 18, 955 (1997); doi:10.1002/(SICI)1096-987X(199705)18:7<955::AID-JCC7>3.0.CO;2-Q.
M. Swart, P.T. van Duijnen and J.G. Snijders, J. Comput. Chem., 22, 79 (2001); doi:10.1002/1096-987X(20010115)22:1<79::AID-JCC8>3.0.CO;2-B.
R.F.W. Bader, Atoms in Molecules - A Quantum Theory, Oxford, London (1990).
J. Cioslowski, J. Am. Chem. Soc., 111, 8333 (1989); doi:10.1021/ja00204a001.
M. Frisch, I.N. Ragazos, M.A. Robb and H. Bernhard Schlegel, Chem. Phys. Lett., 189, 524 (1992); doi:10.1016/0009-2614(92)85244-5.
J.P. Foster and F. Weinhold, J. Am. Chem. Soc., 102, 7211 (1980); doi:10.1021/ja00544a007.
A.E. Reed and F. Weinhold, J. Chem. Phys., 78, 4066 (1983); doi:10.1063/1.445134.
A.E. Reed, R.B. Weinstock and F. Weinhold, J. Chem. Phys., 83, 735 (1985); doi:10.1063/1.449486.
A.E. Reed, L.A. Curtiss and F. Weinhold, Chem. Rev., 88, 899 (1988); doi:10.1021/cr00088a005.
F. Weinhold and J.E. Carpenter, The Structure of Small Molecules and Ions, Plenum, New York, p. 227 (1988).
X. Xu and W.A. Goddard, Proc. Natl. Acad. Sci. USA, 101, 2673 (2004); doi:10.1073/pnas.0308730100.
J. Pernak, R. Kordala, B. Markiewicz, F. Walkiewicz, M. Poplawski, A. Fabianska, S. Jankowski and M. Lozynski, RSC Adv., 2, 8429 (2012); doi:10.1039/c2ra21502k.
S. Chen, R. Vijayaraghavan, D.R. MacFarlane and E.I. Izgorodina, J. Phys. Chem. B, 117, 3186 (2013); doi:10.1021/jp310267x.
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian, Inc., Wallingford CT, Gaussian 09, Revision A 02, Gaussian, Inc, Wallingford, CT (2009).
P. Gu, R. Lü, S. Wang, Y. Lu and D. Liu, Comput. Theoret. Chem., 1020, 22 (2013); doi:10.1016/j.comptc.2013.06.038.
S.S. Batsanov, Experimental Foundations of Structural Chemistry, Moscow University Press, Moscow (2008).
S. Sebastian and N. Sundaraganesan, Spectrochim. Acta A, 75, 941 (2010); doi:10.1016/j.saa.2009.11.030.
I.H. Joe, I. Kostova, C. Ravikumar, M. Amalanathan and S.C. Pînzaru, J. Raman Spectrosc., 40, 1033 (2009); doi:10.1002/jrs.2226.
S. Dapprich and G. Frenking, J. Phys. Chem., 99, 9352 (1995); doi:10.1021/j100023a009.

References

D.M. D'Alessandro, B. Smit and J.R. Long, Angew. Chem. Int. Ed., 49, 6058 (2010); doi:10.1002/anie.201000431.

E.D. Bates, R.D. Mayton, I. Ntai and J.H. Davis, J. Am. Chem. Soc., 124, 926 (2002); doi:10.1021/ja017593d.

C.Y. Hong, C.Y. Fei, D.D. Shun, A. Ning and Z. Yong, J. Mol. Liq., 199, 7 (2014); doi:10.1016/j.molliq.2014.06.023.

F. Jensen, Introduction to Computational Chemistry, Wiley & Sons, Chichester, Chp. 9 (1999).

R.S. Mulliken, J. Chem. Phys., 23, 1833 (1955); doi:10.1063/1.1740588.

U.C. Singh and P.A. Kollman, J. Comput. Chem., 5, 129 (1984); doi:10.1002/jcc.540050204.

A.J. Stone and M. Alderton, Mol. Phys., 56, 1047 (1985); doi:10.1080/00268978500102891.

L.E. Chirlian and M.M. Francl, J. Comput. Chem., 8, 894 (1987); doi:10.1002/jcc.540080616.

C.M. Breneman and K.B. Wiberg, J. Comput. Chem., 11, 361 (1990); doi:10.1002/jcc.540110311.

D.E. Williams, Rev. Comput. Chem., 2, 219 (1991); doi:10.1002/9780470125793.ch6.

C.A. Reynolds, J.W. Essex and W.G. Richards, J. Am. Chem. Soc., 114, 9075 (1992); doi:10.1021/ja00049a045.

C. Aleman, M. Orozro and F.J. Luque, Chem. Phys., 189, 573 (1994); doi:10.1016/0301-0104(94)00310-6.

U. Koch and E. Egert, J. Comput. Chem., 16, 937 (1995); doi:10.1002/jcc.540160803.

D.S. Marynick, J. Comput. Chem., 18, 955 (1997); doi:10.1002/(SICI)1096-987X(199705)18:7<955::AID-JCC7>3.0.CO;2-Q.

M. Swart, P.T. van Duijnen and J.G. Snijders, J. Comput. Chem., 22, 79 (2001); doi:10.1002/1096-987X(20010115)22:1<79::AID-JCC8>3.0.CO;2-B.

R.F.W. Bader, Atoms in Molecules - A Quantum Theory, Oxford, London (1990).

J. Cioslowski, J. Am. Chem. Soc., 111, 8333 (1989); doi:10.1021/ja00204a001.

M. Frisch, I.N. Ragazos, M.A. Robb and H. Bernhard Schlegel, Chem. Phys. Lett., 189, 524 (1992); doi:10.1016/0009-2614(92)85244-5.

J.P. Foster and F. Weinhold, J. Am. Chem. Soc., 102, 7211 (1980); doi:10.1021/ja00544a007.

A.E. Reed and F. Weinhold, J. Chem. Phys., 78, 4066 (1983); doi:10.1063/1.445134.

A.E. Reed, R.B. Weinstock and F. Weinhold, J. Chem. Phys., 83, 735 (1985); doi:10.1063/1.449486.

A.E. Reed, L.A. Curtiss and F. Weinhold, Chem. Rev., 88, 899 (1988); doi:10.1021/cr00088a005.

F. Weinhold and J.E. Carpenter, The Structure of Small Molecules and Ions, Plenum, New York, p. 227 (1988).

X. Xu and W.A. Goddard, Proc. Natl. Acad. Sci. USA, 101, 2673 (2004); doi:10.1073/pnas.0308730100.

J. Pernak, R. Kordala, B. Markiewicz, F. Walkiewicz, M. Poplawski, A. Fabianska, S. Jankowski and M. Lozynski, RSC Adv., 2, 8429 (2012); doi:10.1039/c2ra21502k.

S. Chen, R. Vijayaraghavan, D.R. MacFarlane and E.I. Izgorodina, J. Phys. Chem. B, 117, 3186 (2013); doi:10.1021/jp310267x.

M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian, Inc., Wallingford CT, Gaussian 09, Revision A 02, Gaussian, Inc, Wallingford, CT (2009).

P. Gu, R. Lü, S. Wang, Y. Lu and D. Liu, Comput. Theoret. Chem., 1020, 22 (2013); doi:10.1016/j.comptc.2013.06.038.

S.S. Batsanov, Experimental Foundations of Structural Chemistry, Moscow University Press, Moscow (2008).

S. Sebastian and N. Sundaraganesan, Spectrochim. Acta A, 75, 941 (2010); doi:10.1016/j.saa.2009.11.030.

I.H. Joe, I. Kostova, C. Ravikumar, M. Amalanathan and S.C. Pînzaru, J. Raman Spectrosc., 40, 1033 (2009); doi:10.1002/jrs.2226.

S. Dapprich and G. Frenking, J. Phys. Chem., 99, 9352 (1995); doi:10.1021/j100023a009.

Issue

Vol. 28 No. 1 (2016): Vol 28 Issue 1

Theoretical Studies on Interaction Between CO2 Gas and Imidazolium-Type Organic Ionic Liquid Using DFT and Natural Bond Orbital Calculations

Corresponding Author(s) : Saied M. Soliman

Abstract

Keywords

Full Article

Download Citation

References

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