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2010 | 8 | 3 | 486-493
Tytuł artykułu

Adduct formed by chromium trioxide and zwitterionic quinolinic acid

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Chromium trioxide forms an adduct with zwitterionic quinolinic acid. The structure of the product was found to be (quinolinium-3-carboxylato-O)trioxidochromium(VI), determined by single-crystal X-ray diffraction methods. To evaluate the bonding properties of the compound, its structure was optimized at the B3LYP/6-311G* level of theory. The electronic characteristics were investigated by topological methods applied to the total charge density in various model compounds including the title compound, title compound with a HF molecule presenting a hydrogen bonding and anionic moiety. Calculated aromaticity indices indicate that the quinolinic rings tend to conserve their degree of aromaticity against hydrogen bonding. However, when there is hydrogen bonding involving an N-H bond or when the quinolinium zwitterion is deprotonated, there are clear changes in the interaction between chromium trioxide and the quinolinic moiety. [...]
Wydawca

Czasopismo
Rocznik
Tom
8
Numer
3
Strony
486-493
Opis fizyczny
Daty
wydano
2010-06-01
online
2010-04-25
Twórcy
  • Department of Chemistry, Laboratory of Inorganic Chemistry, University of Helsinki, PO Box 55, FIN-00014, Helsinki, Finland, markku.sundberg@helsinki.fi
autor
  • Department of Chemistry, Laboratory of Inorganic Chemistry, University of Helsinki, PO Box 55, FIN-00014, Helsinki, Finland
  • Department of Chemistry, Laboratory of Inorganic Chemistry, University of Jyväskylä, PO Box 35, FIN-40351, Jyväskylä, Finland
  • Faculty of Chemistry, Jagiellonian University, 30-060, Kraków, Poland
  • Department of Chemistry and Industrial Chemistry, University of Pisa, 56126, Pisa, Italy
  • Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, PO Box 55, FIN-00014, Helsinki, Finland
autor
  • Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, PO Box 55, FIN-00014, Helsinki, Finland
autor
  • Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, PO Box 55, FIN-00014, Helsinki, Finland
Bibliografia
  • [1] G. Cainelli, G. Cardillo, Chromium Oxidations in Organic Chemistry (Springer-Verlag, Berlin, 1984)
  • [2] G.P. Haight, D.C. Richardson, N.H. Coburn, Inorg. Chem. 3, 253 (1963)
  • [3] S.A. Frenneson, J.K. Beattie, G.P. Haight, J. Am. Chem. Soc. 90, 6018 (1968) http://dx.doi.org/10.1021/ja01024a014[Crossref]
  • [4] (a) V. Amirthalingam, D.F. Grant, A. Senol, Acta Crystallogr. B. 28, 1340 (1972) [Crossref]
  • [5] M. Dobler, J.D. Dunitz, B. Gubler, H.P. Weber, G. Buchi, J.O. Padilla, Proc. Chem. Soc., London, 383 (1963)
  • [6] P. Stavropoulos, N. Bryson, M.-T. Youinou, J.A. Osborn, Inorg. Chem. 29, 1807 (1990) http://dx.doi.org/10.1021/ic00335a009[Crossref]
  • [7] C. Lopez, A. Gonzalez, F.P. Cossio, C. Palomo, Synth. Commun. 15, 1197 (1985) http://dx.doi.org/10.1080/00397918508077265[Crossref]
  • [8] S. Patel, B. K. Mishra, Tetrahedron 63, 4367 (2007) http://dx.doi.org/10.1016/j.tet.2007.02.073[Crossref]
  • [9] D.C. McCain, J. Phys. Chem. 79, 1102 (1975) http://dx.doi.org/10.1021/j100578a014[Crossref]
  • [10] (a) J.K.T. Matikainen, S.A.A. Kaltia, T.A. Hase, M.R. Sundberg, R. Kivekäs, J. Chem. Research (S) 150 (1990)
  • [11] J.K.T. Matikainen, S.A.A. Kaltia, T.A. Hase, M.R. Sundberg, R. Kivekäs, J. Chem. Research (M), 1117 (1990)
  • [12] K.V. Gothelf, K.A. Jorgensen, Chem. Rev. 98, 863 (1998) http://dx.doi.org/10.1021/cr970324e[Crossref]
  • [13] T.S. Cameron et al., Can. J. Chem. 81, 612 (2003) http://dx.doi.org/10.1139/v03-042[Crossref]
  • [14] J. Matikainen, S. Kaltia, T. Hase, P. Kuronen, J. Natur. Prod. 58, 1622 (1995) http://dx.doi.org/10.1021/np50124a026[Crossref]
  • [15] J. Matikainen, S. Kaltia, T. Hase, I. Kilpeläinen, T. Drakenberg, A. Annila, Tetrahedron 49, 8007 (1993) http://dx.doi.org/10.1016/S0040-4020(01)88024-8[Crossref]
  • [16] J. Matikainen, S. Kaltia, T. Hase, Synth. Commun. 25, 195 (1995) http://dx.doi.org/10.1080/00397919508010807[Crossref]
  • [17] (a) M. Torrent, L. Deng, M. Duran, M. Sola, T. Ziegler, Can. J. Chem. 77, 1476 (1999)
  • [18] T. Ziegler, J. Li, Organometallics 14, 214 (1995) http://dx.doi.org/10.1021/om00001a033[Crossref]
  • [19] A.C.T. North, D.C. Phillips, F.S. Mathews, Acta Cryst. A 24, 467, (1968) http://dx.doi.org/10.1107/S0567739468000707[Crossref]
  • [20] G.M. Sheldrick, Acta Cryst. A 64, 112 (2008) http://dx.doi.org/10.1107/S0108767307043930[Crossref]
  • [21] L.J. Farrugia, J. App. Cryst., 30, 565 (1997) http://dx.doi.org/10.1107/S0021889897003117[Crossref]
  • [22] M.J. Frisch et al., Gaussian 03, Revision D.02 (Gaussian, Inc., Wallingford CT, 2004)
  • [23] (a) R.F.W. Bader, Atoms in Molecules: A Quantum Theory (Oxford University Press, New York, 1990)
  • [24] P.L.A. Popelier, Atoms in Molecules: An Introduction (Pearson Education, Harlow, 2000)
  • [25] H. Martinez-Garcia, J.A. Dobado, J. Molina, M.R. Sundberg, J. Am. Chem. Soc. 120, 8461 (1998) http://dx.doi.org/10.1021/ja980141p[Crossref]
  • [26] P.L.A. Popelier with a contribution from R.G.A. Bone, program MORPHY98 (UMIST: Manchester, England, 1998)
  • [27] F. Biegler-König, J. Schönbohm, AIM2000, Version 2.0, http://www.aim2000.de
  • [28] F.W. Biegler-König, R.W.W. Bader, T-H. Tang, J. Comput. Chem. 3, 317 (1982) http://dx.doi.org/10.1002/jcc.540030306[Crossref]
  • [29] S. Noury, X. Krokidis, F. Fuster and B. Silvi, Comput. Chem. 23 (1999) 597 http://dx.doi.org/10.1016/S0097-8485(99)00039-X[Crossref]
  • [30] I. Alkorta, O. Picazo, Arkivoc ix, 305 (2005)
  • [31] A.L. Spek, Acta Cryst. A 46, 34 (1990); A.L. Spek PLATON - A Multipurpose Crystallographic Tool (Utrecht University, Utrecht, The Netherlands, 2003)
  • [32] T.M. Krygowski, M.K. Cyranski, Z. Czarnocki, G. Hafelinger, A.R. Katritzky, Tetrahedron 56, 1783 (2000) http://dx.doi.org/10.1016/S0040-4020(99)00979-5[Crossref]
  • [33] T.M. Krygowski, J. Chem. Inf. Comput. Sci. 33, 70 (1993) [Crossref]
  • [34] P.R. von Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N.J.R. Hommes, J. Am. Chem. Soc. 118, 6317 (1996) http://dx.doi.org/10.1021/ja960582d[Crossref]
  • [35] P.R. von Schleyer et al., Org. Lett. 3, 2465 (2001) http://dx.doi.org/10.1021/ol016217v[Crossref]
  • [36] K. Woliński, J.F. Hilton, P. Pulay, J. Am. Chem. Soc. 112, 8251 (1990) http://dx.doi.org/10.1021/ja00179a005[Crossref]
  • [37] http://www.webelements.com
  • [38] G.B. Deacon, R.J. Phillips, Coord. Chem. Rev. 33, 227 (1980) http://dx.doi.org/10.1016/S0010-8545(00)80455-5[Crossref]
  • [39] H.L. Krauss, Angew. Chem. 70, 502 (1958) http://dx.doi.org/10.1002/ange.19580701605[Crossref]
  • [40] X. Fradera, M.A. Austen, R.F. Bader, J. Phys. Chem. A, 103, 304 (1999) http://dx.doi.org/10.1021/jp983362q[Crossref]
  • [41] Z. Chen, C.S. Wannere, C. Corminboeuf, R. Puchta, P.R. von Schleyer, Chem. Rev. 105, 3842 (2005) http://dx.doi.org/10.1021/cr030088+[Crossref]
  • [42] T.M. Krygowski, M.K. Cyranski, Tetrahedron 52, 10255 (1996) http://dx.doi.org/10.1016/0040-4020(96)00560-1[Crossref]
  • [43] A.R. Katritzky, K. Jug, D.C. Oniciu, Chem. Rev. 101, 1421 (2001) http://dx.doi.org/10.1021/cr990327m[Crossref]
  • [44] H. Masui, Coord. Chem Rev. 219–221, 957 (2001) http://dx.doi.org/10.1016/S0010-8545(01)00389-7[Crossref]
  • [45] K. Zborowski, L.M. Proniewicz, Pol. J. Chem. 78, 2219 (2004)
  • [46] M. Kalinowska, E. Siemieniuk, A. Kostro, W. Lewandowski, J. Mol. Struct. THEOCHEM 761, 129 (2006) http://dx.doi.org/10.1016/j.theochem.2006.01.005[Crossref]
  • [47] M.K. Milcic, B.D. Ostojic, S.D. Zaric, Inorg. Chem. 46, 7109 (2007) http://dx.doi.org/10.1021/ic062292w[Crossref]
  • [48] H. Szatylowicz, T.M. Krygowski, Pol. J. Chem. 78, 1719 (2004)
  • [49] T.M. Krygowki, H. Szatylowicz, J.E. Zachara, J. Chem. Inf. Comp. Sci. 44, 2077 (2004) [Crossref]
  • [50] T.M. Krygowski, K. Ejsmont, B.T. Stepien, M.K. Cyranski, J. Poater, M. Sola, J. Org. Chem. 69, 6634 (2004) http://dx.doi.org/10.1021/jo0492113[Crossref]
  • [51] T.M. Krygowski, M.A. Dobrowolski, K. Zborowski, M.K. Cyranski, J. Phys. Org. Chem. 19, 889 (2006) http://dx.doi.org/10.1002/poc.1039[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-010-0033-z
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