Aromatic properties of 8-hydroxyquinoline and its metal complexes

• Autorzy: Krzysztof Zborowski , Miquel Solá , Jordi Poater , Leonard Proniewicz
• Języki publikacji: EN

Abstrakty

EN

Chelatoaromaticity (aromaticity of chelate complexes) has been recently recognized as an important property influencing the stability of chelate compounds. In this paper, aromaticity of various forms of 8-hydroxyquinoline (anion, neutral molecule, zwitterion and cation) as well as its chelate complexes with magnesium and aluminium ions are investigated. Aromatic properties of these compounds are analyzed using several aromaticity indices based on energetic, geometric, magnetic and electronic physical manifestations of this phenomenon. Results of performed calculations have shown different aromatic properties for the two rings (pyridine and benzene) occurring in the studied ligand. Aromaticity of these rings in metal complexes of 8-hydroxyquinoline is significantly higher than that in corresponding ligand anion. This means that during complexation the aromaticity of the ligand increases and the chelatoaromatic effect stabilizes the studied metal complexes. In contrast, metallocyclic rings of studied metal complexes have non-aromatic properties, and, consequently, the metallocyclic ring is not stabilized by chelatoaromaticity. We conclude that, in the complex, every 8-hydroxyquinoline unit and the metal ion are separated p-electronic systems. [...]

Słowa kluczowe

EN

8-hydroxyquinoline; Aromaticity; Chelatocomplexes; Chelatoaromaticity

• Czasopismo: Open Chemistry
• Rocznik: 2013
• Tom: 11
• Numer: 5
• Strony: 655-663

Daty

wydano

2013-05-01

online

2013-02-27

Twórcy

autor

Krzysztof Zborowski

• Faculty of Chemistry, Jagiellonian University, 30-060, Kraków, Poland,

autor

Miquel Solá

• Institute of Computational Chemistry and Department of Chemistry, Girona University, 17071, Girona, Catalonia, Spain

autor

Jordi Poater

• Institute of Computational Chemistry and Department of Chemistry, Girona University, 17071, Girona, Catalonia, Spain

autor

Leonard Proniewicz

Bibliografia

• [1] S. Chabereck, A.E. Martell, Organic Sequestering Agents (Wiley, New York, 1959)
• [2] A.E. Martell, M. Calvin, Chemistry of the Metal Chelate Compounds (Prentice Hall, Englewood Cliffs, 1959)
• [3] C.W. Tang, S.A. Van Slyke, Appl. Phys. Lett. 51, 913 (1987) http://dx.doi.org/10.1063/1.98799[Crossref]
• [4] R.E. Bambury, Burger’s Medicinal Chemistry, Part II (John Wiley, New York, 1979)
• [5] U.S. Department of Health and Human Resources, Toxicology and Carcinogenesis Studies of 8-hydroxyquinoline in F344/N Rats and B6C3F1 Mice, CAS NO. 149-24-3 (1985)
• [6] M.L. Thakur, J.P. Lavender, R.N. Arnot, D.J. Silvester, A.W. Segal, J. Nucl. Med. 18, 1012 (1977)
• [7] M.L. Thakur, A.W. Segar, L. Louis, M.J. Welch, J. Hopkins, T.J. Peters, J. Nucl. Med. 18, 1020 (1977)
• [8] P.M. Chrisholm, H.J. Danpure, G. Healey, S. Osman, J. Nucl. Med. 20, 1308 (1979)
• [9] A.I. Kassis, S.J. Adelstein, J. Nucl. Med. 26, 187 (1985)
• [10] I. Kartsonakis, I. Daniilidis, G. Kordas, J. Sol-Gel. Sci. Technol. 48, 24 (2008) http://dx.doi.org/10.1007/s10971-008-1810-4[Crossref]
• [11] M. Calvin, K.W. Wilson, J. Am. Chem. Soc. 67, 2003 (1945) http://dx.doi.org/10.1021/ja01227a043[Crossref]
• [12] M. Kuhr, H. Musso, Angew. Chem. 81, 150 (1969) http://dx.doi.org/10.1002/ange.19690810408[Crossref]
• [13] M.K. Milčić, B.D. Ostojić, S.D. Zarić, Inorg. Chem. 46, 7109 (2007) http://dx.doi.org/10.1021/ic062292w[Crossref]
• [14] H. Masui, Coord. Chem. Rev. 219–221, 957 (2001) http://dx.doi.org/10.1016/S0010-8545(01)00389-7[Crossref]
• [15] A.D. Becke, J. Chem. Phys. 98, 5648 (1993) http://dx.doi.org/10.1063/1.464913[Crossref]
• [16] C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 37, 785 (1988) http://dx.doi.org/10.1103/PhysRevB.37.785[Crossref]
• [17] P.J. Stevens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, J. Phys. Chem. 98, 11623 (1994) http://dx.doi.org/10.1021/j100096a001[Crossref]
• [18] A.D. McLean, G. S. Chandler, J. Chem. Phys. 72, 5639 (1980) http://dx.doi.org/10.1063/1.438980[Crossref]
• [19] K.K. Zborowski, M. Solà, J. Poater, L.M. Proniewicz, J. Phys. Org. Chem. 24, 499 (2011) http://dx.doi.org/10.1002/poc.1794[Crossref]
• [20] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian’ 03 (Gaussian, Inc., Pittsburgh PA, 2003)
• [21] M.K. Cyrański, T.M. Krygowski, A.R. Katritzky, P.v.R. Schleyer, J. Org. Chem. 67, 1333 (2002) http://dx.doi.org/10.1021/jo016255s[Crossref]
• [22] F. Feixas, E. Matito, J. Poater, M. Solà, J. Comput. Chem. 29, 1543 (2008) http://dx.doi.org/10.1002/jcc.20914[Crossref]
• [23] T.M. Krygowski, J. Chem. Inf. Comput. Sci. 33, 70 (1993) http://dx.doi.org/10.1021/ci00011a011[Crossref]
• [24] P.v.R. Schleyer, C. Marker, A. Dransfeld, H.J. Jiao, N.J.R. van Eikema Hommes, J. Am. Chem. Soc. 118, 6317 (1996) http://dx.doi.org/10.1021/ja960582d[Crossref]
• [25] P.v.R. Schleyer, H. Jiao, N.J.R. van Eikema Hommes, V.G. Malkin, O.L. Malkina, J. Am. Chem. Soc. 119, 12669 (1997) http://dx.doi.org/10.1021/ja9719135[Crossref]
• [26] P.v.R. Schleyer, M. Monohar, Z. Wang, B. Kiran, H. Jiao, R. Puchta, N.J.R. van Eikema Hommes, Org. Lett. 3, 2465 (2001) http://dx.doi.org/10.1021/ol016217v[Crossref]
• [27] Z. Chen, C.S. Wannere, C. Corminboeuf, R. Puchta, P.v.R. Scheyer, Chem. Rev. 105, 3842 (2005) http://dx.doi.org/10.1021/cr030088+[Crossref]
• [28] H. Fallah-Bagher-Shaidaei, C.S Wannere, C. Corminboeuf. R. Puchta, P.v.R. Schleyer, Org. Lett. 8, 863 (2006) http://dx.doi.org/10.1021/ol0529546[Crossref]
• [29] M. Palusiak, T.M. Krygowski, Chem. Eur. J. 13, 7996 (2007) http://dx.doi.org/10.1002/chem.200700250[Crossref]
• [30] J. Poater, X. Fradera, M. Duran, M. Solà, Chem. Eur. J. 9, 400 (2003) http://dx.doi.org/10.1002/chem.200390041[Crossref]
• [31] E. Matito, M. Duran, M. Solà, J. Chem. Phys 122, 014109 (2005) http://dx.doi.org/10.1063/1.1824895[Crossref]
• [32] M. Gambiagi, M. Segre de Gambiagi, C.D. dos Santos Silva, A. Paiva de Figueiredo, Phys. Chem. Chem. Phys. 2, 3381 (2000) http://dx.doi.org/10.1039/b002009p[Crossref]
• [33] P. Bultinck, R. Ponec, S. van Damme, J. Phys. Org. Chem. 18, 706 (2005) http://dx.doi.org/10.1002/poc.922[Crossref]
• [34] P. Bultinck, M. Rafat, R. Ponec, B. van Gheluve, R. Carbó-Dorca, P. Popelier, J. Phys. Chem. A 110, 7642 (2006) http://dx.doi.org/10.1021/jp0609176[Crossref]
• [35] P.v.R. Schleyer (Ed.), Chem. Rev. 101, 1115 (2001) [Crossref]
• [36] P.v.R. Schleyer (Ed.), Chem. Rev. 105, 3433 (2005) [Crossref]
• [37] K. Woliński, J.F. Hilton, P. Pulay, J. Am. Chem. Soc. 112, 8251 (1990) http://dx.doi.org/10.1021/ja00179a005[Crossref]
• [38] R.F.W. Bader, Atoms in molecules. A quantum theory (Oxford University, New York, 1990)
• [39] F.W. Biegler-König, R.F.W Bader, T.H. Tang, J. Comput. Chem. 3, 317 (1982) http://dx.doi.org/10.1002/jcc.540030306[Crossref]
• [40] M.K. Cyrański, P.v.R. Schleyer, T.M. Krygowski, H. Jiao, G. Hohlneicher, Tetrahedron 59, 1657 (2003) http://dx.doi.org/10.1016/S0040-4020(03)00137-6[Crossref]
• [41] P.v.R. Schleyer, F. Pűhlhofer, Org. Lett. 2, 2873 (2002) http://dx.doi.org/10.1021/ol0261332[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] F. Feixas, E. Matito, J. Poater, M. Solà J. Phys. Chem. A 111, 4513 (2007) http://dx.doi.org/10.1021/jp0703206[Crossref]
• [44] H. SzatyŁowicz, T. M. Krygowski, M. Palusiak, J. Poater, M. Solà, J. Org. Chem. 76, 550 (2011) http://dx.doi.org/10.1021/jo102065e[Crossref]
• [45] M.K. Cyrański, M. Gilski, M. Jaskolski, T.M. Krygowski, J. Org. Chem. 68, 8607 (2003) http://dx.doi.org/10.1021/jo034760e[Crossref]
• [46] M. Palusiak, S. Simon, M. Solà, J. Org. Chem. 71, 5241 (2006) http://dx.doi.org/10.1021/jo060591x[Crossref]
• [47] A.R. Katritzky, K. Jug, D.C. Oniciu, Chem. Rev. 101, 1421 (2001) http://dx.doi.org/10.1021/cr990327m[Crossref]
• [48] T.M. Krygowski, M.K. Cyranski, Chem. Rev. 101, 1385 (2001) http://dx.doi.org/10.1021/cr990326u[Crossref]
• [49] J. Poater, I. García-Cruz, F. Illas, M. Solà, Phys. Chem. Chem. Phys. 6, 314 (2004) http://dx.doi.org/10.1039/b309965b[Crossref]

Identyfikatory

DOI

10.2478/s11532-013-0215-6