Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access April 25, 2010

Adduct formed by chromium trioxide and zwitterionic quinolinic acid

Markku Sundberg EMAIL logo , Rolf Uggla , Reijo Sillanpää , Krzysztof Zborowski , Angel Sánchez-González , Jorma Matikainen , Seppo Kaltia and Tapio Hase
From the journal Open Chemistry


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.

[1] G. Cainelli, G. Cardillo, Chromium Oxidations in Organic Chemistry (Springer-Verlag, Berlin, 1984) 10.1007/978-3-642-69362-5Search in Google Scholar

[2] G.P. Haight, D.C. Richardson, N.H. Coburn, Inorg. Chem. 3, 253 (1963) 10.1021/ic50022a028Search in Google Scholar

[3] S.A. Frenneson, J.K. Beattie, G.P. Haight, J. Am. Chem. Soc. 90, 6018 (1968) in Google Scholar

[4] (a) V. Amirthalingam, D.F. Grant, A. Senol, Acta Crystallogr. B. 28, 1340 (1972) 10.1107/S0567740872004261Search in Google Scholar

[5] M. Dobler, J.D. Dunitz, B. Gubler, H.P. Weber, G. Buchi, J.O. Padilla, Proc. Chem. Soc., London, 383 (1963) Search in Google Scholar

[6] P. Stavropoulos, N. Bryson, M.-T. Youinou, J.A. Osborn, Inorg. Chem. 29, 1807 (1990) in Google Scholar

[7] C. Lopez, A. Gonzalez, F.P. Cossio, C. Palomo, Synth. Commun. 15, 1197 (1985) in Google Scholar

[8] S. Patel, B. K. Mishra, Tetrahedron 63, 4367 (2007) in Google Scholar

[9] D.C. McCain, J. Phys. Chem. 79, 1102 (1975) in Google Scholar

[10] (a) J.K.T. Matikainen, S.A.A. Kaltia, T.A. Hase, M.R. Sundberg, R. Kivekäs, J. Chem. Research (S) 150 (1990) Search in Google Scholar

[11] J.K.T. Matikainen, S.A.A. Kaltia, T.A. Hase, M.R. Sundberg, R. Kivekäs, J. Chem. Research (M), 1117 (1990) Search in Google Scholar

[12] K.V. Gothelf, K.A. Jorgensen, Chem. Rev. 98, 863 (1998) in Google Scholar PubMed

[13] T.S. Cameron et al., Can. J. Chem. 81, 612 (2003) in Google Scholar

[14] J. Matikainen, S. Kaltia, T. Hase, P. Kuronen, J. Natur. Prod. 58, 1622 (1995) in Google Scholar

[15] J. Matikainen, S. Kaltia, T. Hase, I. Kilpeläinen, T. Drakenberg, A. Annila, Tetrahedron 49, 8007 (1993) in Google Scholar

[16] J. Matikainen, S. Kaltia, T. Hase, Synth. Commun. 25, 195 (1995) in Google Scholar

[17] (a) M. Torrent, L. Deng, M. Duran, M. Sola, T. Ziegler, Can. J. Chem. 77, 1476 (1999) 10.1139/v99-148Search in Google Scholar

[18] T. Ziegler, J. Li, Organometallics 14, 214 (1995) in Google Scholar

[19] A.C.T. North, D.C. Phillips, F.S. Mathews, Acta Cryst. A 24, 467, (1968) in Google Scholar

[20] G.M. Sheldrick, Acta Cryst. A 64, 112 (2008) in Google Scholar PubMed

[21] L.J. Farrugia, J. App. Cryst., 30, 565 (1997) in Google Scholar

[22] M.J. Frisch et al., Gaussian 03, Revision D.02 (Gaussian, Inc., Wallingford CT, 2004) Search in Google Scholar

[23] (a) R.F.W. Bader, Atoms in Molecules: A Quantum Theory (Oxford University Press, New York, 1990) Search in Google Scholar

[24] P.L.A. Popelier, Atoms in Molecules: An Introduction (Pearson Education, Harlow, 2000) Search in Google Scholar

[25] H. Martinez-Garcia, J.A. Dobado, J. Molina, M.R. Sundberg, J. Am. Chem. Soc. 120, 8461 (1998) in Google Scholar

[26] P.L.A. Popelier with a contribution from R.G.A. Bone, program MORPHY98 (UMIST: Manchester, England, 1998) Search in Google Scholar

[27] F. Biegler-König, J. Schönbohm, AIM2000, Version 2.0, Search in Google Scholar

[28] F.W. Biegler-König, R.W.W. Bader, T-H. Tang, J. Comput. Chem. 3, 317 (1982) in Google Scholar

[29] S. Noury, X. Krokidis, F. Fuster and B. Silvi, Comput. Chem. 23 (1999) 597 in Google Scholar

[30] I. Alkorta, O. Picazo, Arkivoc ix, 305 (2005) 10.3998/ark.5550190.0006.926Search in Google Scholar

[31] A.L. Spek, Acta Cryst. A 46, 34 (1990); A.L. Spek PLATON — A Multipurpose Crystallographic Tool (Utrecht University, Utrecht, The Netherlands, 2003) Search in Google Scholar

[32] T.M. Krygowski, M.K. Cyranski, Z. Czarnocki, G. Hafelinger, A.R. Katritzky, Tetrahedron 56, 1783 (2000) in Google Scholar

[33] T.M. Krygowski, J. Chem. Inf. Comput. Sci. 33, 70 (1993) 10.1021/ci00011a011Search in Google Scholar

[34] P.R. von Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N.J.R. Hommes, J. Am. Chem. Soc. 118, 6317 (1996) in Google Scholar

[35] P.R. von Schleyer et al., Org. Lett. 3, 2465 (2001) in Google Scholar

[36] K. Woliński, J.F. Hilton, P. Pulay, J. Am. Chem. Soc. 112, 8251 (1990) in Google Scholar

[37] Search in Google Scholar

[38] G.B. Deacon, R.J. Phillips, Coord. Chem. Rev. 33, 227 (1980) in Google Scholar

[39] H.L. Krauss, Angew. Chem. 70, 502 (1958) in Google Scholar

[40] X. Fradera, M.A. Austen, R.F. Bader, J. Phys. Chem. A, 103, 304 (1999) in Google Scholar

[41] Z. Chen, C.S. Wannere, C. Corminboeuf, R. Puchta, P.R. von Schleyer, Chem. Rev. 105, 3842 (2005) in Google Scholar

[42] T.M. Krygowski, M.K. Cyranski, Tetrahedron 52, 10255 (1996) in Google Scholar

[43] A.R. Katritzky, K. Jug, D.C. Oniciu, Chem. Rev. 101, 1421 (2001) in Google Scholar

[44] H. Masui, Coord. Chem Rev. 219–221, 957 (2001) in Google Scholar

[45] K. Zborowski, L.M. Proniewicz, Pol. J. Chem. 78, 2219 (2004) Search in Google Scholar

[46] M. Kalinowska, E. Siemieniuk, A. Kostro, W. Lewandowski, J. Mol. Struct. THEOCHEM 761, 129 (2006) in Google Scholar

[47] M.K. Milcic, B.D. Ostojic, S.D. Zaric, Inorg. Chem. 46, 7109 (2007) in Google Scholar PubMed

[48] H. Szatylowicz, T.M. Krygowski, Pol. J. Chem. 78, 1719 (2004) Search in Google Scholar

[49] T.M. Krygowki, H. Szatylowicz, J.E. Zachara, J. Chem. Inf. Comp. Sci. 44, 2077 (2004) 10.1021/ci049817sSearch in Google Scholar PubMed

[50] T.M. Krygowski, K. Ejsmont, B.T. Stepien, M.K. Cyranski, J. Poater, M. Sola, J. Org. Chem. 69, 6634 (2004) in Google Scholar PubMed

[51] T.M. Krygowski, M.A. Dobrowolski, K. Zborowski, M.K. Cyranski, J. Phys. Org. Chem. 19, 889 (2006) in Google Scholar

Published Online: 2010-4-25
Published in Print: 2010-6-1

© 2010 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Downloaded on 30.1.2023 from
Scroll Up Arrow