Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access October 6, 2009

A theoretical study of the neutral and the double-charged cation of cyclo[8]pyrrole and its interaction with inorganic anions

  • Ibon Alkorta EMAIL logo , Fernando Blanco and José Elguero
From the journal Open Chemistry

Abstract

A theoretical study of the complexation of cyclo[8]pyrrole dication, 2, and the corresponding system in neutral form, 3, with six anionic molecules has been carried out up to the B3LYP/6–311++G(2d,2p) computational level. The effect of the water solvation has been taken into account by means of the PCM method. The gas phase results correspond to the very large interaction energies expected for the interaction of molecules of opposite charge. In all the complexes, the analysis of the electron density by means of the Atoms In Molecules (AIM) methodology shows the presence of eight intermolecular interactions between the individual molecules. The results, using the water solvent model, indicate that the 2:SO42− complex is more stable than the 2:NO3−, in agreement with experimental results.

[1] L.R. Eller, M. Stepien, C.J. Fowler, J.T. Lee, J.L. Sessler, B.A. Moyer, J. Am. Chem. Soc. 129, 11020 (2007) http://dx.doi.org/10.1021/ja074568k10.1021/ja074568kSearch in Google Scholar

[2] R. Dagani, Chem. Eng. News, Aug. 27, 11 (2007) 10.1021/cen-v085n009.p011Search in Google Scholar

[3] D. Seidel, V. Lynch, J.L. Sessler, Angew. Chem. Int. Ed. 41, 1422 (2002) http://dx.doi.org/10.1002/1521-3773(20020415)41:8<1422::AID-ANIE1422>3.0.CO;2-O10.1002/1521-3773(20020415)41:8<1422::AID-ANIE1422>3.0.CO;2-OSearch in Google Scholar

[4] M. Stepien, B. Donnio, J.L. Sessler, Angew. Chem. Int. Ed. 46, 1431 (2007) http://dx.doi.org/10.1002/anie.20060389310.1002/anie.200603893Search in Google Scholar

[5] R. Custalcean, B.A. Moyer, Eur. J. Inorg. Chem. 1321 (2007) 10.1002/ejic.200700018Search in Google Scholar

[6] C.J. Fowler et al., J. Am. Chem. Soc. 130, 14386 (2008) http://dx.doi.org/10.1021/ja806511b10.1021/ja806511bSearch in Google Scholar

[7] F. Hofmeister, Arch. Exp. Pathol. Pharmakol. 24, 247 (1888) http://dx.doi.org/10.1007/BF0191819110.1007/BF01918191Search in Google Scholar

[8] F. Hofmeister, Arch. Exp. Pathol. Pharmakol. 25, 1 (1888) http://dx.doi.org/10.1007/BF0196467010.1007/BF01964670Search in Google Scholar

[9] W. Kunz, J. Henle, B.W. Ninham, Curr. Opin. Colloid Interface Sci. 9, 19 (2004) http://dx.doi.org/10.1016/j.cocis.2004.05.00510.1016/j.cocis.2004.05.005Search in Google Scholar

[10] K.D. Collins, M.W. Washabaugh, Q. Rev. Biophys. 18, 323 (1985) http://dx.doi.org/10.1017/S003358350000536910.1017/S0033583500005369Search in Google Scholar

[11] W. Kunz, P. Lo Nostro, B.W. Ninham, Curr. Opin. Colloid Interface Sci. 9, 1 (2004) http://dx.doi.org/10.1016/j.cocis.2004.05.00410.1016/j.cocis.2004.05.004Search in Google Scholar

[12] W. Kunz, Pure Appl. Chem. 78, 1611 (2006) http://dx.doi.org/10.1351/pac20067808161110.1351/pac200678081611Search in Google Scholar

[13] W. Kunz, P. Lo Nostro, B.W. Ninham, Curr. Opin. Colloid Interface Sci. 9, 7 (2004) 10.1016/S1359-0294(04)00059-7Search in Google Scholar

[14] H. Zhao, S.M. Campbell, L. Jackson, Z. Song, O. Olubajo, Tetrahedron Asym. 17, 377 (2006) http://dx.doi.org/10.1016/j.tetasy.2006.01.01510.1016/j.tetasy.2006.01.015Search in Google Scholar

[15] A. Stace, Science 294, 1292 (2001) http://dx.doi.org/10.1126/science.106673110.1126/science.1066731Search in Google Scholar PubMed

[16] N.V. Nucci, J.M. Vanderkooi, J. Mol. Liq. 143, 160 (2008) http://dx.doi.org/10.1016/j.molliq.2008.07.01010.1016/j.molliq.2008.07.010Search in Google Scholar PubMed PubMed Central

[17] A.D. Becke, Phys. Rev. A 38, 3098 (1988) http://dx.doi.org/10.1103/PhysRevA.38.309810.1103/PhysRevA.38.3098Search in Google Scholar

[18] A.D. Becke, J. Chem. Phys. 98, 5648 (1993) http://dx.doi.org/10.1063/1.46491310.1063/1.464913Search in Google Scholar

[19] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988) http://dx.doi.org/10.1103/PhysRevB.37.78510.1103/PhysRevB.37.785Search in Google Scholar

[20] P.A. Hariharan, J.A. Pople, Theor. Chim. Acta 28, 213 (1973) http://dx.doi.org/10.1007/BF0053348510.1007/BF00533485Search in Google Scholar

[21] M.J. Frisch et al., Gaussian 03, Gaussian, Inc., Pittsburgh PA, 2003 Search in Google Scholar

[22] S. Miertus, E. Scrocco, J. Tomasi, J. Chem. Phys. 55, 117 (1981) http://dx.doi.org/10.1016/0301-0104(81)85090-210.1016/0301-0104(81)85090-2Search in Google Scholar

[23] R. Cammi, J. Tomasi, J. Comput. Chem. 16, 1449 (1995) http://dx.doi.org/10.1002/jcc.54016120210.1002/jcc.540161202Search in Google Scholar

[24] R.F.W. Bader, Atoms in Molecules. A Quantum Theory (Oxford University, New York, 1990) Search in Google Scholar

[25] P.L.A. Popelier, with a contribution from R.G.A. Bone, MORPHY98, a topological analysis program (1999) (UMIST, Engl, EU) Search in Google Scholar

[26] F.W. Biegler-König, J. Schönbom, AIM2000, 2.0 edition (Bielefeld, Germany, 2002) Search in Google Scholar

[27] I. Alkorta, O. Picazo, Arkivoc ix, 305 (2005) 10.3998/ark.5550190.0006.926Search in Google Scholar

[28] J. Barrett, Inorganic Chemistry in Aqueous Solution (Royal Society of Chemistry, Cambridge 2004) 184 Search in Google Scholar

[29] I. Alkorta, F. Blanco, J. Elguero, Tetrahedron 64 (2008) 3826 http://dx.doi.org/10.1016/j.tet.2008.01.14110.1016/j.tet.2008.01.141Search in Google Scholar

[30] I. Rozas, I. Alkorta, J. Elguero, J. Am. Chem. Soc. 122, 11154 (2000) http://dx.doi.org/10.1021/ja001786410.1021/ja0017864Search in Google Scholar

[31] I. Alkorta, L. Barrios, I. Rozas, J. Elguero, Theochem. 496, 131 (2000) http://dx.doi.org/10.1016/S0166-1280(99)00177-310.1016/S0166-1280(99)00177-3Search in Google Scholar

[32] O. Picazo, I. Alkorta, J. Elguero, J. Org. Chem. 68, 7485 (2003) http://dx.doi.org/10.1021/jo035026y10.1021/jo035026ySearch in Google Scholar PubMed

[33] I. Mata, I. Alkorta, E. Espinosa, E. Molins, J. Elguero, In: C.F. Matta, R.J. Russell (Eds.), The Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design (Wiley, New York, 2007) 425 Search in Google Scholar

Published Online: 2009-10-6
Published in Print: 2009-12-1

© 2009 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Downloaded on 4.2.2023 from https://www.degruyter.com/document/doi/10.2478/s11532-009-0090-3/html
Scroll Up Arrow