Zjawiska dysocjacji i asocjacji towarzyszące reakcjom przeniesienia protonu między C-kwasami i zasadami organicznymi w rozpuszczalnikach aprotonowych

Nowak, I.; Binkowska, I.; Stańczyk-Dunaj, M.; Jarczewski, A.

Artykuł - szczegóły

Tytuł artykułu

Zjawiska dysocjacji i asocjacji towarzyszące reakcjom przeniesienia protonu między C-kwasami i zasadami organicznymi w rozpuszczalnikach aprotonowych

Autorzy

Nowak I. , Binkowska I. , Stańczyk-Dunaj M. , Jarczewski A.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Dissociation and association effects in proton transfer reactions between C-acids and organic bases in aprotic solvents

Języki publikacji

Abstrakty

The proton transfer reactions in solutions have attracted the attention of a number of laboratories for many years. These processes seem to be quite simple as they proceed without perturbation of bounding electrons and have low steric demands what enables study of their mechanism. However, many factors influences the mechanisms of these reactions. Among them and not the trifling ones, are dissociation-association effects accompanying them. The definition, behavior and reactivity of carbon acids (C-acids) depending on the type of electron withdrawing group are given [1-57]. Also the values of dissociation constants of C-acids in protic and aprotic solvents are collated in Tables 4, 5 and 7 [11, 38, 49]. The nature of products, free ions and ion pairs, of proton transfer reactions of various C-acids and strong organic bases are carefully discussed. Also their spectral characteristics are given. The equilibria and the possible routes between the substrates and the products of these reactions are also shown [58-66]. The reasons of the homoconjugation effects as a result of an association of the ionic products of the proton transfer reactions in different solvents are discussed in the context of their solvation abilities [67-86]. The formation constants of the homoconjugation complexes of amidine and guanidine bases in relation to their pK? values are quoted in Table 6 [87-95]. The nature of heteroconjugation complexes formed as the result of hydrogen bonding of different entities in the system of proton transfer reactions is discussed [96-116]. The pK? values of a number of C-acids, derivatives of nitromethane, measured in acetonitrile by potentiometric method, are given in Table 7. The pK? values of these derivatives measured in DMSO/H2O systems are compared with those obtained in acetonitrile [18, 38]. The general view of these problems is discussed and carefully reviewed.

Słowa kluczowe

przeniesienie protonu C-kwasy silne zasady organiczne dysocjacja asocjacja stałe homo i heterokoniugacji

proton transfer C-acids strong organic bases dissociation association homo and heteroconjugation constants

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2008

Tom

[Z] 62, 1-2

Strony

67--95

Opis fizyczny

bibliogr. 131, tab., wykr.

Twórcy

autor

Nowak I.

autor

Binkowska I.

autor

Stańczyk-Dunaj M.

autor

Jarczewski A.

Zakład Chemii Ogólnej, Wydział Chemii, Uniwersytet im A.Mickiewicza ul. Grunwaldzka 6, 60-780 Poznań

Bibliografia

[1] R.G. Pearson, J. Am. Chem. Soc. 1948, 70, 204.
[2] A. Hantzsch, Ber., 1899,32, 575.
[3] A. Hantzsch, Ber., 1925, 58, 953.
[4] B. Brzeziński, A. Jarczewski, J. Olejnik, G. Schroeder, J. Chem. Soc, PerkinTrans. 2. 1992,2257.
[5] G. Moutiers, V. Thuet, F. Terrier, J. Chem. Soc. Perkin Trans. 2, 1997, 1479 i cytowane tam prace.
[6] G. Moutiers, B. El Fahid, A.G. Collot, F. Terrier, J. Chem. Soc, Perkin Trans. 2, 1996, 49.
[7] R.P. Bell, The Proton in Chemistry, 2nd edn. Chapman and Hall. London 1973.
[8] K.T. Leffek in E. Buncel, C.C. Lee, Isotopes in Organic Chemistry, vol. 2 , Elsevier Pub. Co. Amsterdam, 1976.
[9] O. Exner, T.M. Krygowski, Chem. Soc Rev., 1996, 71.
[10] E.F. Caldin, The Mechanisms of Fast Reactions in Solution, IOS Press, Ohmsha, 2001.
[11] K.T. Leffek, Isot. Org. Chem. 2, 1976, 89, (Isot. Hydrogen Transfer).
[12] E.F. Caldin, A. Jarczewski, K.T. Leffek, Trans. Faraday Soc, 1971. 67. 110.
[13] E.F. Caldin, V. Gold, Proton Transfer Reactions, Chapman and Hall. London. 1975.
[14] E.F. Caldin, Chem. Rev., 1969. 69. 135.
[15] N. Agmon, J. Am. Chem. Soc, 1980, 102, 2164.
[16] CD. Ritchie, .J. Am. Chem. Soc, 1969, 91, 6749.
[17] A. Jarczewski, J. Koput, 1. Nowak. J. Mol. Struct.. 2006, 788, 138.
[18] M. Stańczyk-Dunaj, W. Gałęzowski, A. Jarczewski, Can. J. Chem.. 2002. 80. 1259.
[19] F.G. Bordwell, J.E. Bartmess, J.A. Hautala, J. Org. Chem., 1978, 43. 3095.
[20] J.R. Keeffe. J. Morey. C.A. Palmer, J.C. Lee, J. Am. Chem. Soc, 1979. 101, 1295.
[21] C.F. Bernasconi, Pure and Appl. Chem.. 1982, 54, 2335
[22] A..J. Kresge, Can. J Chem., 1974, 52, 1897.
[23] C.F. Bernasconi, Ace. Chem. Res., 1992, 25, 9.
[24] I. Grześkowiak, W. Gałęzowski. A. Jarczewski, Can. J. Chem., 2001, 79, 1128.
[25] R Schwesinger, Angew. Chem., 1994, 105. 1420.
[26] Ż. Wisłocka, 1. Nowak, A. Jarczewski, J. Mol. Struct., 2006, 788, 152.
[27] K. Minksztym, A. Jarczewski, J. Mol. Struct., 2004, 691, 203.
[28] P. Pruszyński, A. Jarczewski, J. Chem. Soc, Perkin Trans. 2, 1989. 117.
[29] M. Hojatti, K.T. Leffek, Can. J. Chem., 1984, 62,2653.
[30] K.B. Wiberg, H. Castejon, J. Org. Chem., 1995, 60, 6327.
[31] A. Abbotto, S. Bradamante, G.A. Pagani, J. Org. Chem., 1993, 58, 449.
[32] A. Jarczewski, P. Pruszyński, K.T. Leffek, Can. J. Chem., 1979, 57, 669.
[33] A. Jarczewski. P. Pruszyński, K.T. Leffek, Can. J. Chem.. 1983. 61, 2029.
[34] A. Jarczewski, P. Pruszyński, Pol. J. Chem., 1984, 58,1175.
[35] C.F. Bernasconi. Tetrahedron, 1985.41,3219.
[36] C.F. Bernasconi. Acc. Chem. Res., 1987, 20, 301.
[37] C.F. Bernasconi, M.W. Stronach. .J. Am. Chem. Soc.,1990, 112, 8448.
[38] W. Gałęzowski, M. Stańczyk-Dunaj, A. Jarczewski, Can. J. Chem., 1997, 75, 285.
[39] F. Aiken, B.G. Cox, P.E. S0rensen, J. Chem. Soc. Perkin Trans. 2, 1993, 783.
[40] K.P. Ang, W.S. Lee, Aust. J. Chem., 1977, 30. 521.
[41] J. Binkowska, A. Jarczewski, Centr. Eur. J. Chem., 2004, 2, 648.
[42] J. Binkowska, A. Jarczewski, A. Katrusiak, G. Wojciechowski. B. Brzeziński, J. Mol. Struct., 2001, 597,101.
[43] A. Jarczewski, J. Binkowska, Pol. J. Chem., 2001, 75,1895.
[44] J. Binkowska, A. Jarczewski, J. Mol. Struct., 2006, 797, 61.
[45] M. Ludwig, J. Petrzilek, J.Kulhanek, O. Pytela, Collect. Czech. Chem. Commun., 1994, 59. 391.
[46] W. Gałęzowski, I. Grześkowiak, A. Jarczewski, Can. J. Chem., 1999, 77, 1042.
[47] W. Gałęzowski, A. Jarczewski, Can. J. Chem., 1992, 70,935.
[48] W. Gałęzowski, I. Grześkowiak, A. Jarczewski, J. Chem. Soc, Perkin Trans. 2, 1998, 1607.
[49] F. Terrier, E. Kizilian, R. Gaumont, N. Fauchner, C. Wakselman, J. Am. Chem. Soc, 1998, 120, 9496.
[50] R. Goumont. E. Magnier. E. Kizilian, F. Terrier, J. Org. Chem., 2003, 68. 6566.
[51] S. Wolfe, A. Stolow, L. Lajohn, Tetrahedron Lett., 1983, 24, 4071 i przypisy w publikacji.
[52] D.A. Bors, A. Streitwieser, J. Am. Chem. Soc, 1986, 108. 1397 i przypisy w publikacji.
[53] K.B. Wiberg, H. Castejon, J. Am. Chem. Soc, 1994, 116, 10489 i przypisy w publikacji.
[54] G. Schroeder, B. Leska, A. Jarczewski, B. Nowak-Wydra, B. Brzeziński. J. Mol. Struct.. 1995, 344, 77.
[55] R. Schwesinger, Chimia. 1985, 39, 269.
[56] R. Goumont, E. Kizilian, E. Buncel, F. Terrier, Org. Biomol. Chem., 2003. 1, 1741.
[57] F. Terrier, E. Magnier, E. Kizilian, C. Wakselman, E. Buncel. J. Am. Chem. Soc. 2005, 127, 5563.
[58] H.A. Benesi, J.H. Hildebrand, J. Am. Chem. Soc, 1949, 71.2703.
[59] E.F. Caldin. S. Mateo, J. Chem. Soc. Farady Trans. 1. 1975. 1876.
[60] N. Sugimoto, M. Sasaki, J. Osugi, .J. Chem. Soc, Perkin Trans. 2, 1984, 655.
[61] K.T. Leffek, P. Pruszyński, Can. J. Chem.. 1982, 60. 1982.
[62] W. Gałęzowski, A. Jarczewski, J. Chem. Soc, Perkin Trans. 2, 1989. 1647.
[63] l.M. Kolthoff, M.K. Chantooni, J. Am. Chem. Soc, 1967, 90, 3005.
[64] W. Gałęzowski, M. Stańczyk, 1. Grześkowiak, A. Jarczewski. J. Chem. Soc, PerkinTrans. 2, 1996 2647.
[65] B. Brzeziński, P. Radziejewski, G. Zundel, J. Chem. Soc, Faraday Trans., 1995, 91, 3141.
[66] M.K. Chantooni, Jr., I.M. Kolthoff. J. Am. Chem. Soc, 1967. 90, 3005.
[67] D.H. Aue, H.M. Webb, M.T. Bowers, J. Am. Chem. Soc. 1976, 98. 318.
[68J D.H. Aue, H.M. Webb. M.T. Bowers, J. Am. Chem. Soc. 1976, 98, 854.
[69] C. Reichardt, Solvents and Solvent Effects in Organic Chemistry. Wiley-VCH, Weinheim, 2003.
[70] A.A. Maryott, I. Res. Natl. Bur. Stand.. 1947,38, 527.
[71] H.B. Van der Heijde, Anal. Chim. Acta., 1957, 16, 392.
[72] G.A. Harlow. D.B. Bruss, Anal. Chem., 1958, 30, 392.
[73] D.H. Morman, G.A. Harlow. Anal. Chem., 1967. 39, 1869.
[74] I.M. Kolthoff, M.K. Chantooni, .1. Am. Chem. Soc, 1963. 85. 2195.
[75] I-M. Kolthoff, Anal. Chem.. 1974. 46, 1992.
[76] I.M. Kolthoir, M.K. Chantooni, Jr.. J. Am. Chem. Soc. 1965, 87, 4428.
[77] I.M. Kolthoff; Pure and Appl. Chem.. 1971. 25. 305.
[78] J.F. Coetzce. Prog. Phys. Org. Chem., 1967. 4, 45.
[79] M. Roses, Anal. Chim. Acta, 1994. 285. 391.
[80] Z. Pawlak, J. Magoński, F. Strohbusch. J. Chem. Soc. Faraday Trans. 1. 1985. 81, 2021.
[81] .J. Magoński, Z. Pawlak, T. Jasiński. .J. Chem. Soc, Faraday Trans.. 1993, 89, 119.
|82] B.A. Korolev, E.I. Kashkovskaja, Журн. Общ. Химии, 1979. 49, 909.
[83] I.M. Kolthoff, M.K. Chantooni Jr., S. Bhowmik, J. Am. Chem. Soc. 1968. 90, 23.
[84] R.L. Benoit. C. Buisson, Electrochim. Acta, 1973, 18, 105.
[85] Z. Pawlak. Roczniki Chemii, 1973. 47, 347.
[86] M. Persin, J.Y. Gal, Can. J. Chem., 1981, 59, 2491.
[87] B. Brzeziński, M. Szafran, Pol. J. Chem., 1978, 52, 1833.
[88] B. Brzeziński, M. Szafran, Ann. Soc Chim. Polonorum, 1977, 51, 1779.
[89] J.F. Coetzee, G.R. Padmanabhan, J. Am. Chem. Soc, 1965. 87. 5005.
[90] M. Staiiczyk-Dunaj, A. Jarczewski, Pol. J. Chem.. 2005. 79, 1025.
[91] D.D. Perrin, The Dissociation Constants for Organic Bases in Aqueous Solution. Butterworths. London, 1965.
[92] L.A. Kurasov, A.F. Pozharski. V.V. Kuzmenko, Zh. Org. Khim., 1983, 19, 859.
[93] K.T. Leffek, P. Pruszyiiski, K. Thanapaalasingham. Can. J. Chem., 1989, 67, 590.
[94] G. Schroeder. B. Leska, A. Jarczewski, B. Nowak-Wydra, B. Brzeziński. J. Mol. Struct., 1995. 344, 77.
[95] W. Gałęzowski, A. Jarczewski. M. Slańczyk, B. Brzeziński. F. Bartl, G. Zundel, J. Chem. Soc. Faraday Trans.. 1997, 93, 2515.
[96] A.A. Maryott, J. Res. Nat. Bur. Stand.. 1947. 38. 527.
[97] G. Zundel, A. Nagyreci, J. Phys. Chem., 1978, 82, 685.
[98] G. Albrecht, G. Zundel, .1. Chem. Soc. Faraday Trans. 1, 1984, 80. 553.
[99] H. Baba, A. Matsuyama, H. Kokubun, Spectrochim. Acta. 1969, 25A, 1709.
[100] Th. Zeegers-Huyskens. Spectrochim. Acta, 1965,21,221.
[101] R. Lindemann, G. Zundel, .J. Chem. Soc, Faraday Trans. 2, 1972. 68, 979.
[102] Z. Dega-Szafran, A. Hrynio, M. Szafran, J. Mol. Struct., 1990, 240. 159.
[103] M.H. Abraham. P.P. Duce. D.V. Prior, D.G. Barrat, J.J. Morris, P.J. Taylor. J. Chem. Soc, Perkin Trans. 2, 1989, 10, 1355.
[104] P. Adamek, P. Endrle, Z. Ksandr, Collect. Czechoslov. Chem. Commun., 1971. 36. 3539.
[105] S.F. Bureiko, N.S. Golubev, J. Mattinen, K. Pihlaya, J. Mol. Liquids, 1990, 45, 139.
[106] T. Gramstad, L..I. Stangeland. Acta. Chem. Scand., 1993. 47, 605.
[107] V.A. Barbash, Yu.Ya. Fiatkov. N.N. Shapetko, Zh. Obshch. Khim.. 1983. 53, 2178.
[108] O.L. Chapman. R.W. King, .J. Am. Chem. Soc. 1964, 86. 1256.
[109] RS. Drago. B.B. Wayland. R.L. Carlson. J. Am. Chem. Soc. 1963, 85. 3125.
[110] T. Gramstad. Spectrochim. Acta, 1963, 19, 829.
[111] J. Hine. S. Hahn, D.F.. Miles, J. Org. Chem.. 1986. 51. 577.
[112] H. Fritzsche, Z. Chem.. 1973, 13, 35.
[113] J.D. Morris, R.M. Salinger, F.L. Pilar, J. Org. Chem., 1969. 34, 1497.
[114] A. Massat, A. Cosse-Barbi, J.P. Doucet, J. Chem. Phys., 1985. 82, 821.
[115] A. Massat. A. Cosse-Barbi, J.P. Doucet, J. Mol. Stmct., 1989. 13,212.
[116] O.A. Ponomarev, A.O. Doroshenko, O.E. Bondarenko, V.G. Mitina. Zh. Obshch. Khim 1989 59 1475
[117] L. Sobczyk, Ber. Bunsen-Ges. Phys. Chem. Chem. Phys. 1998. 102, 377.
[118] M. Rospenk, L. Sobczyk, A. Rabold, G. Zundel, Speetroch. Acta A., 1999. 55, 855.
[119| B. Tremillon, Chemistry in Non-Aqeuos Solvents, Reidel Publishing Company, Dordrecht. Boston 1974
[120] I.M. Kolthoff. Anal. Chem., 1974. 46, 1992.
[121] L.P. Hammet.A.J. Deyrup, J.Am. Chem. Soc, 1932,54,2721.
[122] CV. Speller, M. Meor-Ner. J. Phys. Chem.. 1985. 89, 5217.
[123] C. Reichardt, Solvent Effects in Organic Chemistry, Verlag Chemie. Weinheim-New York, 1979.
[124] Y. Marcus, The Properties of Solvents, Wiley, West Sussex. 1998.
[125] F.G. Bordwell. J.C. Brauca, D.L. Huges, W.V. Olmstead, J. Org. Chem.. 1980, 45. 3311.
[126] M. Fujio, R.T. Mclver, R.W. Taft. J.Am. Chem. Soc. 1981, 103. 4017.
[127] F.G. Bordwell, J.C. Branca, D.L. Hughes. W.N. Olmstead, J. Org. Chem., 1980. 56, 3305.
[128] F.W. Westheimer, Chem. Rev.. 1996, 61, 265.
[129] A. Jarczewski, CD. Hubbard, J. Mol. Struct., 2003, 649. 287.
[130] R. Schwesinger, Angew. Chem. Int. Ed. Engl., 1987, 26, 1164 .
[131] W.S. Matthews, J.E. Bares, .I.E. Bartmess i in., J. Am. Chem. Soc, 1975. 97, 7006.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS5-0011-0003