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Open Chemistry

formerly Central European Journal of Chemistry


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Volume 9, Issue 1

Issues

Volume 13 (2015)

Can lone pair-π and cation-π interactions coexist? A theoretical study

Carolina Estarellas / Antonio Frontera / David Quiñonero / Pere Deyà
Published Online: 2010-12-16 | DOI: https://doi.org/10.2478/s11532-010-0127-7

Abstract

The interplay between two important noncovalent interactions involving different aromatic rings is studied by means of ab initio calculations (MP2/6-31++G**) computing the non-additivity energies. In this study we demonstrate the existence of cooperativity effects when cation-π and lone pair-π interactions coexist in the same system. These effects are studied theoretically using energetic and geometric features of the complexes. In addition we use Bader’s theory of atoms-in-molecules and Molecular Interaction Potential with polarization (MIPp) partition scheme to characterize the interactions. Experimental evidence for this combination of interactions has been obtained from the Cambridge Structural Database.

Keywords: Noncovalent interactions; Cooperativity effects; Non-additivity energy; Atoms-in-Molecules theory; Energy partition scheme

  • [1] E.A. Meyer, R.K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 42, 1210 (2003) http://dx.doi.org/10.1002/anie.200390319CrossrefGoogle Scholar

  • [2] A.K. Rappé, E.R. Bernstein, J. Phys. Chem. A 104, 6117 (2000) http://dx.doi.org/10.1021/jp0008997CrossrefGoogle Scholar

  • [3] A. Hesselmann, G. Jansen, M. Schütz, J. Am. Chem. Soc. 128, 11730 (2006) http://dx.doi.org/10.1021/ja0633363CrossrefGoogle Scholar

  • [4] M. Piacenza, S. Grimme, Chem. Phys. Chem. 6, 1554 (2005) Google Scholar

  • [5] J.C. Ma, D.A. Dougherty, Chem. Rev. 97, 1303 (1997) http://dx.doi.org/10.1021/cr9603744CrossrefGoogle Scholar

  • [6] J.P. Gallivan, D.A. Dougherty, Proc. Natl. Acad. Sci. USA 96, 9459 (1999) http://dx.doi.org/10.1073/pnas.96.17.9459CrossrefGoogle Scholar

  • [7] G.W. Gokel, S.L.D. Wall, E.S. Meadows, Eur. J. Org. Chem. 2967 (2000) CrossrefGoogle Scholar

  • [8] G.W. Gokel, L.J. Barbour, S.L.D. Wall, E.S. Meadows, Coord. Chem. Rev. 222, 127 (2001) http://dx.doi.org/10.1016/S0010-8545(01)00380-0CrossrefGoogle Scholar

  • [9] G.W. Gokel, L.J. Barbour, R. Ferdani, J. Hu, Acc. Chem. Res. 35, 878 (2002) http://dx.doi.org/10.1021/ar000093pCrossrefGoogle Scholar

  • [10] C.A. Hunter, J. Singh, J.M. Thorton, J. Mol. Biol. 218, 837 (1991) http://dx.doi.org/10.1016/0022-2836(91)90271-7CrossrefGoogle Scholar

  • [11] H. Ishikita, E.W. Knapp, J. Am. Chem. Soc. 129, 1210 (2007) http://dx.doi.org/10.1021/ja066208nCrossrefGoogle Scholar

  • [12] D.A. Dougherty, Science 271, 163 (1996) http://dx.doi.org/10.1126/science.271.5246.163CrossrefGoogle Scholar

  • [13] S.C.R. Lummis, D.L. Beene, N.J. Harrison, H.A. Lester, D.A. Dougherty, Chem. Biol. 12, 993 (2005) http://dx.doi.org/10.1016/j.chembiol.2005.06.012CrossrefGoogle Scholar

  • [14] E. Cubero, F.J. Luque, M. Orozco, Proc. Natl. Acad. Sci. USA 95, 5976 (1998) http://dx.doi.org/10.1073/pnas.95.11.5976CrossrefGoogle Scholar

  • [15] M. Mascal, A. Armstrong, M.D. Bartberger, J. Am. Chem. Soc. 124, 6274 (2002) http://dx.doi.org/10.1021/ja017449sCrossrefGoogle Scholar

  • [16] I. Alkorta, I. Rozas, J. Elguero, J. Am. Chem. Soc. 124, 8593 (2002) http://dx.doi.org/10.1021/ja025693tCrossrefGoogle Scholar

  • [17] D. Quiñonero, C. Garau, C. Rotger, A. Frontera, P. Ballester, A. Costa, P.M. Deyà, Angew. Chem. Int. Ed. 41, 3389 (2002) http://dx.doi.org/10.1002/1521-3773(20020916)41:18<3389::AID-ANIE3389>3.0.CO;2-SCrossrefGoogle Scholar

  • [18] M. Egli, S. Sarkhel, Acc. Chem. Res. 40, 197 (2007) http://dx.doi.org/10.1021/ar068174uCrossrefGoogle Scholar

  • [19] M. Egli, R.V. Gessner, Proc. Natl. Acad. Sci. U.S.A. 92, 180 (1995) http://dx.doi.org/10.1073/pnas.92.1.180CrossrefGoogle Scholar

  • [20] D. Bancroft, L.D. Williams, A. Rich, M. Egli, Biochemistry 33, 1073 (1994) http://dx.doi.org/10.1021/bi00171a005CrossrefGoogle Scholar

  • [21] S. Sarkhel, A. Rich, M. Egli, J. Am. Chem. Soc. 125, 8998 (2003) http://dx.doi.org/10.1021/ja0357801CrossrefGoogle Scholar

  • [22] J.C. Calabrese, D.B. Jordan, A. Boodhoo, S. Sariaslani, T. Vannelli, Biochemistry, 43, 11403 (2004) http://dx.doi.org/10.1021/bi049053+CrossrefGoogle Scholar

  • [23] T.J. Mooibroek, P. Gamez, J. Reedijk, Cryst Eng Comm 10, 1501 (2008) CrossrefGoogle Scholar

  • [24] P. de Hoog, A. Robertazzi, I. Mutikainen, U. Turpeinen, P. Gamez, J. Reedijk, Eur. J. Inorg. Chem. 2684 (2009) Google Scholar

  • [25] P.J. Kitson, Y.F. Song, P. Gamez, P. de Hoog, D.L. Long, A.D.C. Parenty, J. Reedijk, L. Cronin, Inorg. Chem. 47, 1883 (2008) http://dx.doi.org/10.1021/ic7022192CrossrefGoogle Scholar

  • [26] Z.L. Lu, P. Gamez, I. Mutikainen, U. Turpeinen, J. Reedijk, Cryst. Growth Des. 7, 1669 (2007) http://dx.doi.org/10.1021/cg0704302CrossrefGoogle Scholar

  • [27] T.J. Mooibroek, S.J. Teat, C. Massera, J. Reedijk, Cryst. Growth Des. 6, 1569 (2006) http://dx.doi.org/10.1021/cg060144aCrossrefGoogle Scholar

  • [28] R.F.W. Bader, Chem. Rev. 91, 893 (1991) http://dx.doi.org/10.1021/cr00005a013CrossrefGoogle Scholar

  • [29] E. Cubero, M. Orozco, F.J. Luque, J. Phys. Chem. A 103, 315 (1999) http://dx.doi.org/10.1021/jp983382sCrossrefGoogle Scholar

  • [30] I. Alkorta, F. Blanco, P.M. Deya, J. Elguero, C. Estarellas, A. Frontera, D. Quiñonero, Theor. Chem. Acc. 126, 1 (2010) http://dx.doi.org/10.1007/s00214-009-0690-1CrossrefGoogle Scholar

  • [31] F.J. Luque, M. Orozco, J. Comput. Chem. 19, 866 (1998) http://dx.doi.org/10.1002/(SICI)1096-987X(199806)19:8<866::AID-JCC6>3.0.CO;2-NCrossrefGoogle Scholar

  • [32] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, 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, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian-03 (Gaussian, Inc.: Wallingford, CT, 2003) Google Scholar

  • [33] S.B. Boys, F. Bernardy, Mol. Phys. 19, 553 (1970) http://dx.doi.org/10.1080/00268977000101561CrossrefGoogle Scholar

  • [34] F. Biegler-König, J. Schönbohm, D. Bayles, J. Comp. Chem. 22, 545 (2001) http://dx.doi.org/10.1002/1096-987X(20010415)22:5<545::AID-JCC1027>3.0.CO;2-YCrossrefGoogle Scholar

  • [35] E. Sigfridson, U. Ryde, J. Comput. Chem. 19, 377 (1998) http://dx.doi.org/10.1002/(SICI)1096-987X(199803)19:4<377::AID-JCC1>3.0.CO;2-PCrossrefGoogle Scholar

  • [36] F.J. Luque, M. Orozco, MOPETE computer program (University of Barcelona, Barcelona, 1998) Google Scholar

  • [37] B. Hernández, M. Orozco, F.J. Luque, J. Comput. Aided Mol. Des. 11, 153 (1997) http://dx.doi.org/10.1023/A:1008082425628CrossrefGoogle Scholar

  • [38] F.J. Luque, M. Orozco, J. Chem. Soc., Perkin Trans. 2, 683 (1993) CrossrefGoogle Scholar

  • [39] E. Scrocco, J. Tomasi, Top. Curr. Chem. 42, 95 (1973) Google Scholar

  • [40] M. Orozco, F.J. Luque, J. Comput. Chem. 14, 587 (1993) http://dx.doi.org/10.1002/jcc.540140512CrossrefGoogle Scholar

  • [41] M.M. Francl, J. Phys. Chem. 89, 428 (1985) http://dx.doi.org/10.1021/j100249a012CrossrefGoogle Scholar

  • [42] C. Garau, D. Quiñonero, A. Frontera, P. Ballester, A. Costa, P.M. Deya, Org. Lett. 5, 2227 (2003) http://dx.doi.org/10.1021/ol034650uCrossrefGoogle Scholar

  • [43] E. Cubero, M. Orozco, F.J. Luque, J. Phys. Chem. A 103, 315 (1999) http://dx.doi.org/10.1021/jp983382sCrossrefGoogle Scholar

  • [44] W. Zhu, X. Tan, J. Shen, X. Luo, F. Cheng, P.C. Mok, R. Ji, K. Chen, H. Jiang, J. Phys. Chem. A 107, 2296 (2003) http://dx.doi.org/10.1021/jp0270598CrossrefGoogle Scholar

  • [45] C. Estarellas, A. Frontera, D. Quiñonero, I. Alkorta, P.M. Deyà, J. Elguero, J. Phys. Chem. A 113, 3266 (2009) http://dx.doi.org/10.1021/jp811345eCrossrefGoogle Scholar

  • [46] F.H. Allen, Acta Crystallogr. B58, 380 (2002) Google Scholar

  • [47] A. Nangia, K. Biradha, G.R. Desiraju, J. Chem. Soc., Perkin Trans. 2, 943 (1996) CrossrefGoogle Scholar

  • [48] J. Yang, B.R. Nelson, J.A. Weil, J.W. Quail, Act. Cryst. Section C 50, 1548 (1994) http://dx.doi.org/10.1107/S0108270194003045CrossrefGoogle Scholar

  • [49] I.I Zviedre, E.M. Shvarts, V.K. Belskii, Zh. Neorg. Khim. 44, 1994 (1999) Google Scholar

About the article

Published Online: 2010-12-16

Published in Print: 2011-02-01


Citation Information: Open Chemistry, Volume 9, Issue 1, Pages 25–34, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-010-0127-7.

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© 2011 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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