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BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access December 16, 2010

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

  • Carolina Estarellas EMAIL logo , Antonio Frontera , David Quiñonero and Pere Deyà
From the journal Open Chemistry

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.

[1] E.A. Meyer, R.K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 42, 1210 (2003) http://dx.doi.org/10.1002/anie.20039031910.1002/anie.200390319Search in Google Scholar

[2] A.K. Rappé, E.R. Bernstein, J. Phys. Chem. A 104, 6117 (2000) http://dx.doi.org/10.1021/jp000899710.1021/jp0008997Search in Google Scholar

[3] A. Hesselmann, G. Jansen, M. Schütz, J. Am. Chem. Soc. 128, 11730 (2006) http://dx.doi.org/10.1021/ja063336310.1021/ja0633363Search in Google Scholar

[4] M. Piacenza, S. Grimme, Chem. Phys. Chem. 6, 1554 (2005) 10.1002/cphc.200500100Search in Google Scholar

[5] J.C. Ma, D.A. Dougherty, Chem. Rev. 97, 1303 (1997) http://dx.doi.org/10.1021/cr960374410.1021/cr9603744Search in Google Scholar

[6] J.P. Gallivan, D.A. Dougherty, Proc. Natl. Acad. Sci. USA 96, 9459 (1999) http://dx.doi.org/10.1073/pnas.96.17.945910.1073/pnas.96.17.9459Search in Google Scholar

[7] G.W. Gokel, S.L.D. Wall, E.S. Meadows, Eur. J. Org. Chem. 2967 (2000) 10.1002/1099-0690(200009)2000:17<2967::AID-EJOC2967>3.0.CO;2-OSearch in Google 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)00380-010.1016/S0010-8545(01)00380-0Search in Google Scholar

[9] G.W. Gokel, L.J. Barbour, R. Ferdani, J. Hu, Acc. Chem. Res. 35, 878 (2002) http://dx.doi.org/10.1021/ar000093p10.1021/ar000093pSearch in Google 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)90271-710.1016/0022-2836(91)90271-7Search in Google Scholar

[11] H. Ishikita, E.W. Knapp, J. Am. Chem. Soc. 129, 1210 (2007) http://dx.doi.org/10.1021/ja066208n10.1021/ja066208nSearch in Google Scholar

[12] D.A. Dougherty, Science 271, 163 (1996) http://dx.doi.org/10.1126/science.271.5246.16310.1126/science.271.5246.163Search in Google 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.2005.06.01210.1016/j.chembiol.2005.06.012Search in Google Scholar

[14] E. Cubero, F.J. Luque, M. Orozco, Proc. Natl. Acad. Sci. USA 95, 5976 (1998) http://dx.doi.org/10.1073/pnas.95.11.597610.1073/pnas.95.11.5976Search in Google Scholar

[15] M. Mascal, A. Armstrong, M.D. Bartberger, J. Am. Chem. Soc. 124, 6274 (2002) http://dx.doi.org/10.1021/ja017449s10.1021/ja017449sSearch in Google Scholar

[16] I. Alkorta, I. Rozas, J. Elguero, J. Am. Chem. Soc. 124, 8593 (2002) http://dx.doi.org/10.1021/ja025693t10.1021/ja025693tSearch in Google 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-S10.1002/1521-3773(20020916)41:18<3389::AID-ANIE3389>3.0.CO;2-SSearch in Google Scholar

[18] M. Egli, S. Sarkhel, Acc. Chem. Res. 40, 197 (2007) http://dx.doi.org/10.1021/ar068174u10.1021/ar068174uSearch in Google Scholar

[19] M. Egli, R.V. Gessner, Proc. Natl. Acad. Sci. U.S.A. 92, 180 (1995) http://dx.doi.org/10.1073/pnas.92.1.18010.1073/pnas.92.1.180Search in Google Scholar

[20] D. Bancroft, L.D. Williams, A. Rich, M. Egli, Biochemistry 33, 1073 (1994) http://dx.doi.org/10.1021/bi00171a00510.1021/bi00171a005Search in Google Scholar

[21] S. Sarkhel, A. Rich, M. Egli, J. Am. Chem. Soc. 125, 8998 (2003) http://dx.doi.org/10.1021/ja035780110.1021/ja0357801Search in Google Scholar PubMed

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

[23] T.J. Mooibroek, P. Gamez, J. Reedijk, Cryst Eng Comm 10, 1501 (2008) 10.1039/b812026aSearch in Google Scholar

[24] P. de Hoog, A. Robertazzi, I. Mutikainen, U. Turpeinen, P. Gamez, J. Reedijk, Eur. J. Inorg. Chem. 2684 (2009) 10.1002/ejic.200900183Search in 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/ic702219210.1021/ic7022192Search in Google Scholar PubMed

[26] Z.L. Lu, P. Gamez, I. Mutikainen, U. Turpeinen, J. Reedijk, Cryst. Growth Des. 7, 1669 (2007) http://dx.doi.org/10.1021/cg070430210.1021/cg0704302Search in Google Scholar

[27] T.J. Mooibroek, S.J. Teat, C. Massera, J. Reedijk, Cryst. Growth Des. 6, 1569 (2006) http://dx.doi.org/10.1021/cg060144a10.1021/cg060144aSearch in Google Scholar

[28] R.F.W. Bader, Chem. Rev. 91, 893 (1991) http://dx.doi.org/10.1021/cr00005a01310.1021/cr00005a013Search in Google Scholar

[29] E. Cubero, M. Orozco, F.J. Luque, J. Phys. Chem. A 103, 315 (1999) http://dx.doi.org/10.1021/jp983382s10.1021/jp983382sSearch in Google 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/s00214-009-0690-110.1007/s00214-009-0690-1Search in Google 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-N10.1002/(SICI)1096-987X(199806)19:8<866::AID-JCC6>3.0.CO;2-NSearch in Google 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) Search in Google Scholar

[33] S.B. Boys, F. Bernardy, Mol. Phys. 19, 553 (1970) http://dx.doi.org/10.1080/0026897700010156110.1080/00268977000101561Search in Google 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-Y10.1002/1096-987X(20010415)22:5<545::AID-JCC1027>3.0.CO;2-YSearch in Google 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-P10.1002/(SICI)1096-987X(199803)19:4<377::AID-JCC1>3.0.CO;2-PSearch in Google Scholar

[36] F.J. Luque, M. Orozco, MOPETE computer program (University of Barcelona, Barcelona, 1998) Search in 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:100808242562810.1023/A:1008082425628Search in Google Scholar

[38] F.J. Luque, M. Orozco, J. Chem. Soc., Perkin Trans. 2, 683 (1993) 10.1039/p29930000683Search in Google Scholar

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

[40] M. Orozco, F.J. Luque, J. Comput. Chem. 14, 587 (1993) http://dx.doi.org/10.1002/jcc.54014051210.1002/jcc.540140512Search in Google Scholar

[41] M.M. Francl, J. Phys. Chem. 89, 428 (1985) http://dx.doi.org/10.1021/j100249a01210.1021/j100249a012Search in Google 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/ol034650u10.1021/ol034650uSearch in Google Scholar

[43] E. Cubero, M. Orozco, F.J. Luque, J. Phys. Chem. A 103, 315 (1999) http://dx.doi.org/10.1021/jp983382s10.1021/jp983382sSearch in Google 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/jp027059810.1021/jp0270598Search in Google 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/jp811345e10.1021/jp811345eSearch in Google Scholar PubMed

[46] F.H. Allen, Acta Crystallogr. B58, 380 (2002) 10.1107/S0108768102003890Search in Google Scholar PubMed

[47] A. Nangia, K. Biradha, G.R. Desiraju, J. Chem. Soc., Perkin Trans. 2, 943 (1996) 10.1039/P29960000943Search in Google 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/S010827019400304510.1107/S0108270194003045Search in Google Scholar

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

Published Online: 2010-12-16
Published in Print: 2011-2-1

© 2011 Versita Warsaw

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