Change of the tautomeric preference for radical cation of pyruvic acid. DFT studies in the gas phase
Subject Areas : Journal of the Iranian Chemical Research
Ewa Daniela
Raczyńska
1
(Department of Chemistry, Warsaw University of Life Sciences, 02-776 Warszawa, Poland)
Malgorzta
Hallmann
2
(Department of Chemistry, Warsaw University of Life Sciences, 02-776 Warszawa, Poland)
Kinga
Duczmal
3
(Department of Chemistry, Warsaw University of Life Sciences, 02-776 Warszawa, Poland)
Keywords:
Abstract :
[1] (a) A.J. Kresge, Pure Appl. Chem. 63 (1991) 213, (b) A.J. Kresge, Chem. Soc. Rev. 25 (1996) 275.
[2] (a)Z. Rappoport, The Chemistry of Enols, Wiley, Chichester, 1990, (b) Z. Rappoport, J. Fre, M. Sigalo, E. Rochli, Pure Appl. Chem. 69 (1997) 1933, (c) F.G. Bordwell, S. Zhang, I. Eventova, Z. Rappoport, J. Org. Chem. 62 (1997) 5371, (d) M. Mishima, Mustanir, I. Eventova, Z. Rappoprt, J. Chem. Soc. Perkin Trans. 2 (2000) 1505, (e) Z. Rappoport, The Chemistry of Phenols, Wiley, Chichester, 2003.
[3] (a) A. Fontana, P. de Maria, G. Siani, M. Pierini, S. Cerritelli, R. Ballini, Eur. J. Org. Chem. (2000) 1637, (b) E. Iglesias, Current Org. Chem. 8 (2004) 1.
[4] (a) P. Tarakeshwar, S. Manogaran, J. Mol. Struct. (Theochem) 430 (1998) 51, (b) Z. Zhou, D. Du, A. Fu, Vib. Spectrosc. 23 (2000) 181, (c) C. Chen, S.F. Shyu, J. Mol. Struct. (Theochem) 503 (2000) 201, (d) I.D. Reva, S.G. Stephanian, L. Adamowicz, R. Fausto, J. Phys. Chem. A 105 (2001) 4773, (e) X.Yang, X.J. Orlova, X.J. Zhou, K.T. Leung, Chem. Phys. Lett. 380 (2003) 34.
[5] (a) E.D. Raczyńska, K. Duczmal, M. Darowska, Pol. J. Chem. 79 (2005) 689, (b) E.D. Raczyńska, K. Duczmal, M. Darowska, Vibr. Spectrosc. 39 (2005) 37, (c) R. Kakkar, M. Pathak, N.P. Radhika, Org. Biomol. Chem. 4 (2006) 886.
[6] W.J. Ray, J.E. Katon, D.B. Philips, J. Mol. Struct. 74 (1981) 75.
[7] (a) M.C. Pirrung, J. Chen, E.G. Rowley, A.T. McPhail, J. Am. Chem. Soc. 115 (1993) 7103, (b) T. Tatai, H. Senda, H.H. Lee, A. Kuwae, K. Hanai, Spectrosc. Lett. 31 (1998) 379, (c) A.J.M. Carpy, P.P. Haasbroek, J. Ouhabi, D.W. Oliver, J. Mol. Struct. 520 (2000) 191, (d) B. Bartolini, C. Corniello, F. Sella, V. Somma, V. Politi, Dev. Tryptophan Serotonin Metab. 527 (2003) 527, (e) A. Evidente, A. Andolfi, M.A. Abouzeid, M. Vurro, M.C. Zonna, A. Motta , Phytochemical 65 (2004) 475.
[8] U. Weiss, J.M. Edwards, The Biosynthesis of Aromatic Compounds, Wiley, New York, 1980.
[9] (a) S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin, W.G. Mallard, J. Phys. Ref. Data Suppl. 1 (1988) 17, (b) W. Bertrand, G. Bouchoux, Rapid Commun. Mass Spectrom., 12 (1998) 1697, (c) G. van der Rest, T.B. Mourgues, J. Tortajada, H.E. Audier, Int. J. Mass Spectrom. 179-180 (1998) 293, (d) G. van der Rest, H. Nedev, P. Chamot-Rooke, T.B. Mourgues, T.B. McMahonm, E.H. Audier, Int. Mass Spectrom. 202 (2000) 161, (e) D.J. McAdoo, J. Mass Spectrom. Rev. 19 (2000) 38.
[10] R.G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
[11] (a) C. Lee, W. Yang, R.G. Parr, Phys. Rev. 37 (1988) 785, (b) A.D. Becke, Phys. Rev. B 38 (1988) 3098.
[12] L. Rodríguez-Santiago, O. Vendrell, I. Tejero, M. Sodupe, J. Bertran, Chem. Phys. Lett. 334 (2001) 112.
[13] (a) W.J. Hehre, L. Radom, P.v.R. Schleyer, J.A. Pople, Ab initio Molecular Theory, Wiley, New York, 1986, (b) D.E. Woon, T.H. Dunning, J. Chem. Phys. 98 (1993) 1358, (c) F. Jensen, Introduction to Computational Chemistry, Wiley, New York, 1999.
[14] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Jr. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Oritz, A.G. Baboul, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople Gaussian 98, Gaussian, Inc., Pittsburgh PA, 1998.
[15] (a) C.C. Wu, M.H. Lien, J. Phys. Chem. 100 (1996) 594, (b) C.C. Su, C.K. Lin, C.C. Wu, M.H. Lien, J. Phys. Chem. A 103 (1999) 3289.
[16] (a) E.D. Raczyńska, Anal. Chim. Acta 348 (1997) 431, (b) E.D. Raczyńska, R. Gawinecki, Trends Org. Chem. 7 (1998) 85, (c) E.D. Raczyńska, Pol. J. Chem. 73 (1999) 1863, (d) E.D. Raczyńska, Pol. J. Chem. 74 (2000) 1283, (e) E.D. Raczyńska, T. Rudka, M. Darowska, J. Mol. Struct. (Theochem) 574 (2001) 221, (f) E.D. Raczyńska, M. Darowska, M.K. Cyrański, M. Makowski, T. Rudka, J.F. Gal, P.C. Maria, J. Phys. Org. Chem. 16 (2003) 783, (g) E.D. Raczyńska, T. Krygowski, J.E. Zachara, B. Ośmiałowski, R. Gawinecki, J. Phys. Org. Chem. 18 (2005) 892.
[17] (a) B.J. Smith, M.T. Nguyen, W.J. Bouma, L. Radom, J. Am. Chem. Soc. 113 (1991) 6452, (b) B.J. Smith, L. Radom, J. Am. Chem. Soc. 112 (1990) 7525.
[18] E.D. Raczyńska, T.M. Krygowski, K. Duczmal, M. Hallmann, XVIII International Conference on Physical Organic Chemistry, Warsaw, 2006.
[19] T.M. Krygowski, J. Chem. Inf. Comput. Sci. 33 (1993) 70.
[20] (a) J. Kruszewski, T.M. Krygowski, Bull. Acad. Pol. Sci., Ser. Sci. Chim. 20 (1972) 907, (b) J. Kruszewski, T.M. Krygowski, Tetrahedron Lett. (1972) 3839, (c) T.M. Krygowski, J. Kruszewski, Bull. Acad. Pol. Sci., Ser. Sci. Chim. 21 (1973) 409, (d) T.M. Krygowski, J. Kruszewski, Bull. Acad. Pol. Sci., Ser. Sci. Chim. 22 (1974) 871.
