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Induced aromaticity

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Abstract

The influence of counterions on the stabilization of three-, five-, and six-membered cyclic organic and organoboron systems was studied by the ab initio (MP2(full)/6-311+G**) and density functional (B3LYP/6-311+G**) methods. The structures of molecular charge-transfer molecular complexes formed by the interaction with counterions are predicted. A crucial role of counterions in the stabilization of aromatic systems that are unstable in themselves was revealed. Stabilization of these systems involves both charge transfer and covalent bonding.

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References

  1. V. I. Minkin, M. N. Glukhovtsev, and B. Ya. Simkin, Aromaticity and Antiaromaticity: Electronic and Structural Aspects, Wiley, New York, 1994.

    Google Scholar 

  2. S. Masamune, Pure Appl. Chem., 1975, 44, 861.

    Google Scholar 

  3. D. W. Kohn and P. Chen, J. Am. Chem. Soc., 1993, 115, 2844.

    Google Scholar 

  4. R. Lefebre and N. Moiseyev, J. Am. Chem. Soc., 1990, 112, 5052.

    Google Scholar 

  5. G. V. Zandwijk, R. A. J. Janssen, and H. M. Buck, J. Am. Chem. Soc., 1990, 112, 4155.

    Google Scholar 

  6. M. Balci, M. L. McKee, and P. v. R. Schleyer, J. Phys. Chem., A, 2000, 104, 1246.

    Google Scholar 

  7. A. Sekiguchi, T. Matsuo, and H. Watanabe, J. Am. Chem. Soc., 2000, 122, 5652.

    Google Scholar 

  8. M. Traetteberg, Acta Chem. Scand., 1966, 20, 1724.

    Google Scholar 

  9. L. A. Paquette, Tetrahedron, 1975, 31, 2855; Pure Appl. Chem., 1982, 54, 987.

    Google Scholar 

  10. F. A. L. Anet, J. Am. Chem. Soc., 1962, 84, 671.

    Google Scholar 

  11. J. F. M. Oth, Pure Appl. Chem., 1971, 25, 573.

    Google Scholar 

  12. D. A. Hrovat and W. T. Borden, J. Am. Chem. Soc., 1992, 114, 5879.

    Google Scholar 

  13. S. W. Staley, R. A. Grimm, P. Boman, and B. Eliasson, J. Am. Chem. Soc., 1999, 121, 7182.

    Google Scholar 

  14. Ions and Ion Pairs in Organic Reaction, Ed. M. Szwarc, Wiley-Interscience, New York, 1972.

    Google Scholar 

  15. A. Streitwieser, S. M. Bachrach, A. Dorigo, and P. v. R. Schleyer, in Lithium Chemistry, Eds. A.-M. Sapse and P. v. R. Schleyer, Wiley, New York, 1995, P. 1.

    Google Scholar 

  16. Charge Transfer Complexes in Biological Systems, Eds. F. Gutman, C. Johnson, H. Keyzer, and J. Molar, Marcel Dekker, New York, 1997.

    Google Scholar 

  17. C. C. Sines, L. McFail-Isom, S. B. Howerton, D. VanDerveer, and L. D. Williams, J. Am. Chem. Soc., 2000, 122, 11048.

    Google Scholar 

  18. S. R. Gadre and S. S. Pingale, J. Am. Chem. Soc., 1998, 120, 7056.

    Google Scholar 

  19. O. P. Charkin, Stabil'nost' i struktura gazoobraznykh neorganicheskikh molekul, radikalov i ionov [Stability and Structure of Inorganic Molecules, Radicals, and Ions in the Gas Phase], Nauka, Moscow, 1980, 278 (in Russian).

    Google Scholar 

  20. R. M. Minyaev, Zh. Neorg. Khim., 2000, 45, 1182 [Russ. J. Inorg. Chem., 2000, 45 (Engl. Transl.)].

    Google Scholar 

  21. H. Jiao, P. v. R. Schleyer, Y. Mo, M. A. McAllister, and T. T. Tidwell, J. Am. Chem. Soc., 1997, 119, 7075.

    Google Scholar 

  22. D. B. Grotjahn, T. C. Pesch, M. A. Brewster, and L. M. Ziarys, J. Am. Chem. Soc., 2000, 122, 4735.

    Google Scholar 

  23. V. I. Minkin, R. M. Minyaev, and Yu. A. Zhdanov, Nonclassical Structures of Organic Compounds, Mir Publishers, Moscow, 1987.

    Google Scholar 

  24. R. Breslow, G. Ryan, and J. T. Groves, J. Am. Chem. Soc., 1970, 92, 4735.

    Google Scholar 

  25. R. Curci, J. Org. Chem., 1973, 38, 3149.

    Google Scholar 

  26. G. A. Dushenko, I. E. Mikhailov, I. V. Dorogan, R. M. Minyaev, N. Hakam, A. Zschunke, and V. I. Minkin, Mendeleev Commun., 1995, 213.

  27. P. Piotrowiak and J. R. Miller, J. Phys. Chem., 1993, 97, 13052 (this is a special issue of J. Phys. Chem. concerning charge transfer studies).

    Google Scholar 

  28. Introduction to Molecular Electronics, Eds. M. S. Petty, M. R. Bryce, and D. Bloor, Oxford University Press, New York, 1995, 387 pp.

    Google Scholar 

  29. M. Essefar, W. Bouab, A. Lamsabhi, J.-L. M. Abboud, R. Notario, and M. Yanez, J. Am. Chem. Soc., 2000, 122, 2300.

    Google Scholar 

  30. J. B. Foresman and E. Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed., Gaussian, Inc., Pittsburgh (PA), 1996, 302 pp.

    Google Scholar 

  31. M. J. Frish, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, GAUSSIAN-94, Revision B.3, Gaussian, Inc., Pittsburgh (PA), USA, 1995.

    Google Scholar 

  32. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, and J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347 (GAMESS, Version 1996).

    Google Scholar 

  33. R. M. Minyaev, Usp. Khim., 1994, 63, 939 [Russ. Chem. Rev., 1994, 63, 883 (Engl. Transl.)].

    Google Scholar 

  34. PC MODEL, Selena Software, Bloomington (IN), USA, 1987.

  35. P. J. Garrat, Aromaticity, Wiley, New York, 1986.

    Google Scholar 

  36. E. D. Jemmis, G. Subramania, and S. N. Srinivas, J. Am. Chem. Soc., 1992, 114, 7939.

    Google Scholar 

  37. M. W. Wong and L. Radom, J. Am. Chem. Soc., 1989, 111, 6976 (cited therein are references to earlier studies).

    Google Scholar 

  38. F. H. Allen, Tetrahedron, 1982, 38, 645.

    Google Scholar 

  39. M. Hargittai and I. Hargittai, The Molecular Geometries of Coordination Compounds in Vapour Phase, Akademiai Kiado, Budapest, 1975.

    Google Scholar 

  40. K. S. Krasnov, N. V. Filippenko, V. A. Bobkova, N. L. Lebedeva, E. V. Morozov, T. I. Ustinova, and G. A. Romanova, Molekulyarnye postoyannye neorganicheskikh soedinenii [Molecular Constants of Inorganic Compounds], Khimiya, Leningrad, 1979, 446 pp. (in Russian).

    Google Scholar 

  41. Yu. V. Zefirov and P. M. Zorkii, Usp. Khim., 1995, 64, 446 [Buss. Chem. Rev., 1995, 64 (Engl. Transl.)].

    Google Scholar 

  42. L. V. Gurvich, G. V. Karachevtsev, V. N. Kondrat'ev, Yu. F. Lebedev, V. A. Medvedev, V. K. Potapov, and Yu. S. Khodeev, Energii razryva khimicheskikh svyazei. Potentsialy ionizatsii i srodstvo k elektronu [Chemical Bond Cleavage Energies. Ionization Potentials and Electron Affinity], Nauka, Moscow, 1974 (in Russian).

    Google Scholar 

  43. V. I. Minkin, I. V. Dorogan, and R. M. Minyaev, J. Mol. Struct. (THEOCHEM), 1997, 398–399, 237.

    Google Scholar 

  44. M. E. Volpin, Yu. D. Koreshkov, V. G. Dulova, and D. N. Kursanov, Tetrahedron, 1962, 18, 107.

    Google Scholar 

  45. K. Krogh-Jespersen, D. Cremer, J. D. Dill, J. A. Pople, and P. v. R. Schleyer, J. Am. Chem. Soc., 1981, 103, 2589.

    Google Scholar 

  46. J. J. Eisch, B. Shafii, J. D. Odom, and A. L. Rheingold, J. Am. Chem. Soc., 1990, 112, 1847.

    Google Scholar 

  47. D. V. Lanzisera, P. Hassanzadeh, Y. Hannachi, and L. Andrews, J. Am. Chem. Soc., 1997, 119, 12402.

    Google Scholar 

  48. N. Balucani, O. Asvany, Y. T. Lee, R. I. Kaiser, N. Galland, and Y. Hannachi, J. Am. Chem. Soc., 2000, 122, 11234.

    Google Scholar 

  49. R. Wehrmann, H. Meyer, and A. Berndt, Angew. Chem., Int. Ed. Engl., 1985, 24, 788.

    Google Scholar 

  50. H. Meyer, G. Schmidt-Lukasch, G. Baum, W. Massa, and A. Berndt, Z. Naturforsch., Teil B, 1988, 43, 801.

    Google Scholar 

  51. P. Power, Inorg. Chim. Acta, 1992, 198–200, 443.

    Google Scholar 

  52. A. F. Wells, Structural Inorganic Chemistry, Clarendon Press, Oxford, 1986.

    Google Scholar 

  53. J. Emsley, The Elements, Clarendon Press, Oxford, 1991.

    Google Scholar 

  54. J. J. Eisch, J. E. Galle, and S. Kozima, J. Am. Chem. Soc., 1986, 108, 379.

    Google Scholar 

  55. G. E. Herberich, G. Gress, and H. F. Heil, Angew. Chem., Int. Ed. Engl., 1970, 9, 805.

    Google Scholar 

  56. G. E. Herberich, in Comprehensive Ogranometalic Chemistry II, Eds. E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon Press, Oxford, 1995, 1, p. 197.

    Google Scholar 

  57. B. Y. Lee, S. Wang, M. Putzer, G. P. Bartholomew, X. Bu, and G. C. Bazan, J. Am. Chem. Soc., 2000, 122, 3969.

    Google Scholar 

  58. G. E. Herberich, B. Schmidt, U. Unglert, and T. Wagner, Organometallics, 1993, 12, 2891.

    Google Scholar 

  59. J. S. Rogers, R. J. Lachicotte, and G. C. Bazan, J. Am. Chem. Soc., 1999, 121, 1288.

    Google Scholar 

  60. J. M. Schulman, R. L. Disch, and M. L. Sabio, J. Am. Chem. Soc., 1982, 104, 3785.

    Google Scholar 

  61. J. Cioslowski and P. J. Hay, J. Am. Chem. Soc., 1990, 112, 1707.

    Google Scholar 

  62. R. E. Williams, Chem. Rev., 1992, 92, 177.

    Google Scholar 

  63. T. Onak, M. Diaz, and M. Barfield, J. Am. Chem. Soc., 1995, 117, 1403.

    Google Scholar 

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Minyaev, R.M., Minkin, V.I., Starikov, A.G. et al. Induced aromaticity. Russian Chemical Bulletin 50, 2325–2335 (2001). https://doi.org/10.1023/A:1015067025720

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