PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2010 | 8 | 3 | 486-493
Article title

Adduct formed by chromium trioxide and zwitterionic quinolinic acid

Content
Title variants
Languages of publication
EN
Abstracts
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. [...]
Publisher
Journal
Year
Volume
8
Issue
3
Pages
486-493
Physical description
Dates
published
1 - 6 - 2010
online
25 - 4 - 2010
References
  • [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]
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-010-0033-z
Identifiers
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.