Theoretical Study of the Formation of Complexes Between CO and Nitrogen Heterocycles

Authors

  • Adela Lemus-Santana Centro?de?Investigación?en?Ciencia?Aplicada?y?Tecnología?Avanzada,?Unidad?Legaria,?Instituto?Politécnico?Nacional,?México? D.F.
  • Elizabeth Hernández-Marín Centro?de?Investigación?en?Ciencia?Aplicada?y?Tecnología?Avanzada,?Unidad?Legaria,?Instituto?Politécnico?Nacional,?México? D.F.

DOI:

https://doi.org/10.29356/jmcs.v59i1.12

Keywords:

CO2 scrubbers, DFT, dispersion corrections, imidazole derivatives, pyrazine

Abstract

A density functional theory study was performed to analyze the formation of complexes between CO2 and different nitrogen heterocycles such as imidazole, 2-methylimidazole, benzimidazole, and pyrazine. Two orientations of CO2 were considered: in-plane and top-on with respect to the plane of the heterocyclic ring. The in-plane complexes are more stable than their top-on counterparts, most likely due to electrostatic and Lewis acid-base interactions. The strength of the intermolecular interactions in the top-on complexes can be related to a combination of dispersion, weak electrostatic, dipole-quadrupole and quadrupole-quadrupole interactions, and to some extent to the interactions where some charge transfer from the ring to CO2 is involved. With respect to a potential use as CO2 scrubbers, imidazole and its derivatives appear to be better than pyrazine.

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References

http://www.epa.gov/climatechange/ccs/#important, accessed in June 2014.

House, K. Z.; Baclig, A. C.; Ranjan, M.; van Nierop, E. A.; Wilkox, J.; Herzog, H. J. Proc. Nat. Acad. Sci. U.S.A. 2011, 108, 20428-20433.

Rochelle, G. T. Science 2009, 325, 1652-1654.

Arstad, B.; Blom, R. Swang, O. J. Phys. Chem. A 2007, 111, 122-1228.

Pera-Titus, M. Chem. Rev. 2014, 114, 1413-1492.

Simmons, J. M.; Wu, H.;Zhou, W.; Yildirim, T. Energy Environ. Sci. 2011, 4, 2177-2185.

Sumida, K.; Rogow, D. L.; Mason, J. A.; McDonald, T. M.; Bloch, E. D.; Herm, Z. R.; Bae, T.-H.; Long, J. R. Chem. Rev. 2012, 112, 724-781.

Phan, A.; Doonan, C. J.; Uribe-Romo, F. J.; Knobler, C. B.; O'Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2010, 43, 58-67.

Ruiz, E.; Alvarez, E.; Hoffmann, R.; Bemstein, J. J . Am. Chem. Soc. 1994, 116, 8207-8221.

Ruiz, E.; Novoa, J. J.; Alvarez, S. J. Phys. Chem. 1995, 99, 2296-2306.

Ruiz, E.; Alvarez, S. Inorg. Chem. 1995, 34, 3260-3269.

Culp, J. T.; Smith, M. R.; Bittner, E.; Bockrath, B. J. Am. Chem. Soc. 2008, 130, 12427–12434.

Culp, J. T.; Natesakhawat, S.; Smith, M. R.; Bittner, E.; Matranga, C.; Bockrath, B. J. Phys. Chem. C 2008, 112, 7079-7083.

Culp, J. T.; Madden, C.; Kauffman, K.; Shi, F.; Matranga, C. Inorg. Chem. 2013, 52, 4205?4216.

Gonzalez, M.; Lemus-Santana, A. A.; Rodriguez-Hernandez, J.; Knobel, M.; Reguera, E. J. Solid State Chem. 2013, 197, 317-322.

Gonzalez, M.; Lemus-Santana, A. A.; Rodriguez-Hernandez, J.; Aguirre-Velez, C. I.; Knobel, M.; Reguera, E. J. Solid State Chem. 2013, 204, 128-135.

Rodriguez-Hernandez, J.; Lemus-Santana, A. A.; Ortiz-López, J.; Jiménez-Sandoval, S.; Reguera, E. J. Solid State Chem. 2010, 183, 105–113.

Jorgensen, K. R.; Cundari, T. R.; Wilson, A. K. J. Phys. Chem. A 2012, 116, 10403-10411.

Hussain, M. A.; Soujanya, Y.; Sastry, G. N. Environ. Sci.Technol. 2011, 45, 8582-8588.

Cundari, T. R.; Wilson, A. K.; Drummond, M. L.; Gonzalez, H. E.; Jorgensen, K. R.; Payne, S.; Braunfeld, J.; De Jesus, M,; Johnson, V. M. J. Chem. Inf. Model. 2009, 49, 2111-2115.

Torrisi, A.; Mellot-Draznieks, C.; Bell, R. G. J. Chem. Phys. 2009, 130, 194703.

Torrisi, A.; Mellot-Draznieks, C.; Bell, R. G. J. Chem. Phys. 2010, 132, 044705.

Chen, L.; Cao, F.; Sun, H. Int. J. Quantum Chem .2013, 113, 2261-2266.

Vogiatzis, K. D.; Mavrandonakis, A.; Klopper, W.; Froudakis, G. E. ChemPhysChem 2009, 10, 374-383.

Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory and Comput. 2006, 2, 364-82.

Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104.

Grimme, S. WIREs.Comput. Mol. Sci. Chem. 2011, 1, 211-228.

(a) Valdes, H.; Pluha?kova, K.; Pitonák, M.; ?ezá?, J.; Hobza, P. Phys. Chem. Chem. Phys. 2008, 10, 2747-2757. (b) Goerigk, L. Grimme, S. Phys. Chem. Chem. Phys., 2011, 13, 6670-6688. (c) Schneebeli, S. T.; Bochevaron, A. D.; Friesner, R. A. J. Chem. Theory Comput. 2011, 7, 658–668. (d) Zawada, A.; Kaczmarek-K?dziera, A.; Bartkowiak, W. J. Mol. Model. 2012, 18, 3073-3086. (e) Sedlack, R.; Janowski, T.; Pito?ák, M.; ?ezá?, J.; Pulay, P.; Hobza, P. J. Chem. Theory Comput., 2013, 9, 3364–3374.

(a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864. (b) W. Kohn, L. Sham. Phys. Rev. 1965, 140, A1133.

Gaussian 09, Revision D.01, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. et al., Gaussian, Inc., Wallingford CT, 2009.

Becke, A. D. J. Chem. Phys.1993, 98, 5648-5652.

Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 785-789.

Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.

Morokuma, K.; Kitaura, K. Energy Decomposition Analysis of Molecular Interactions. In Chemical Applications of Atomic and Molecular Electrostatic Potentials; Politzer, P., Truhlar, D. G., Eds.; Springer: New York, 1981; p 216.

Jensen, F. Introduction to Computational Chemistry. 2nd ed.; John Wiley & Sons: England, 2007; p 226-227.

Boys, S. F.; Barnardy, F. Mol. Phys. 1970, 19, 553-556.

Glendening, E.D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1.

Arnold, D. W.; Bradforth, S. E.; Kim, E. H.; Neumark, D. M. J. Chem. Phys. 1995, 102, 3493-3509.

Aresta, M. Carbon Dioxide Reduction and Uses as a Chemical Feedstock, In Activation of Small Molecules; Tolman, W. B, Ed.; Wiley-VCH: Germany, 2006; p 3.

Freund, H.-J.; Roberts, M. W. Surf. Sci. Rep. 1996, 25, 225-273.

Deshmukh, M. M.; Ohba, M.; Kitagawa, S.; Sakaki, S. J. Am. Chem. Soc. 2013, 135, 4840-4849.

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Published

2017-10-12

Issue

Vol. 59 No. 1 (2015): Regular Issue

Section

Regular Articles

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