The effect of remote substitution on formation of preferential geometrical isomer of cobalt(III)-tetrazolato complexes formed via [2 + 3] cycloaddition

Inorganic Chemistry Communications

Volumn 34, Issue , 2013, Pages 62-67

  Saha, Manideepa ^a   Nasani, Rajendar ^a   Mobin, Shaikh M ^a   Pathak, Biswarup ^a   Mukhopadhyay, Suman ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY INDORE   (India)

Author keywords

Cobalt complex; Cycloaddition; DFT; Geometrical isomers; Tetrazoles

Indexed keywords

EID: 84878240512     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2013.04.022     Document Type: Article

References (34)

1. In: V.A. Ostrovskii, G.I. Koldobskii, R.E. Trifonov, A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, R.J.K. Taylor (Eds.), Volume 6: other five-membered rings with three or more heteroatoms, and their fused carbocyclic derivatives, in comprehensive heterocyclic chemistry III, Elsevier, Oxford, 2008, pp. 257-423.
2. P.N. Gaponik, S.V. Voitekhovich, O.A. Ivashkevich, Metal derivatives of tetrazoles, Russ. Chem. Rev. 75 (2006) 507-539. (Pubitemid 44898374)
3. J.R. Anacona, P. Alvarez, Synthesis and antibacterial activity of metal complexes of cefazolin, Transit. Met. Chem. 27 (2002) 856-860;
4. (b) Z.H. Chohan, C.T. Supuran, A. Scozzafava, Metalloantibiotics: synthesis and antibacterial activity of cobalt(II), copper(II), nickel(II) and zinc(II) complexes of kefzol, J. Enzyme Inhib. Med. Chem. 19 (2004) 79-84. (Pubitemid 38239933)
5. E.A. Popova, R.E. Trifonov, V.A. Ostrovskii, Advances in the synthesis of the tetrazoles coordinated to metal ions and references therein, ARKIVOC (i) (2012) 45-65.
6. (a) Y. Qiu, Y. Li, G. Peng, J. Cai, L. Jin, Li Ma, H. Deng, M. Zeller, S.R. Batten, Cadmium metal-directed three-dimensional coordination polymers: in situ tetrazole ligand synthesis, structures, and luminescent properties, Cryst. Growth Des. 10 (2010) 1332-1340;
7. (b) Z. Li, M. Li, X.-P. Zhou, T. Wu, D. Li, S.W. Ng, Metal-directed supramolecular architectures: from mononuclear to 3D frameworks based on in situ tetrazole ligand synthesis, Cryst. Growth Des. 7 (2007) 1992-1998.
8. (a) S. Mukhopadhyay, J. Lasri, M.A.J. Charmier, M.F.C. Guedes da Silva, A.J.L. Pombeiro, Microwave synthesis of mono- and bis-tetrazolato complexes via 1,3-dipolar cycloaddition of organonitriles with platinum(II)-bound azides, Dalton Trans. (2007) 5297-5304; (Pubitemid 350115400)
9. (b) P. Smoleński, S. Mukhopadhyay, M.F.C. Guedes da Silva, M.A.J. Charmier, A.J.L. Pombeiro, New water-soluble azido- and derived tetrazolato-platinum(II) complexes with PTA. Easy metal-mediated synthesis and isolation of 5-substituted tetrazoles, Dalton Trans. (2008) 6546-6555;
10. (c) R. Nasani, M. Saha, S.M. Mobin, S. Mukhopadhyay, Microwave synthesis of mono- and bis-tetrazolato complexes via 1,3-dipolar cycloaddition of organonitriles with nickel(II)-bound azides: isolation of 5-substituted tetrazoles from parent complex, Polyhedron 55 (2013) 24-36.
11. (a) B.G. Mukhopadhyay, S. Mukhopadhyay, M.F.C. Guedes da Silva, M.A.J. Charmier, A.J.L. Pombeiro, Synthesis of mono- and bis-tetrazolato complexes of Ni(II), Pt(II) and Cu(II) via 1,3-dipolar cycloadditions of 2-cyanopyridines with metal ligated azides in N,N,O-aminoiminophenolato complexes, Dalton Trans. (2009) 4778-4785;
12. (b) P. Paul, K. Nag, Sulfur-nitrogen-bonded metal chelates. 18. 1,3-Dipolar cycloadditions to coordinated azide in nickel(II) complexes of the types [Ni(S-N-N)(N3)] and [S-N-N)Ni(N3)Ni(N-N-S)](ClO4), Inorg. Chem. 26 (1987) 2969-2974;
13. (c) T. Kemmerich, J.H. Nelson, N.E. Takach, H. Boebme, B. Jablonski, W. Beck, 1,3-Dipolar cycloadditions to coordinated azide in cobalt chelate complexes of the type LCo(chelate)N3, Inorg. Chem. 21 (1982) 1226-1232.
14. 2, Acta Crystallogr. 39 (1983) 567-570.
15. Yang Chen, You Song, Yong Zhang, Jian-Ping Lang, A tricobalt(II) coordination polymer incorporating in situ generated 5-methyltetrazolate ligands, Inorg. Chem. Commun. 11 (2008) 572-575.
16. M.E. Kastner, D.A. Smith, J.N. Cooper, A.G. Kuzmission, T. Tyree, M. Yearick, Structural trans effects in some bis(ethylenediamine)cobalt(III) complexes, Inorg. Chim. Acta 158 (1989) 185-199;
17. *-cis- dichlorobis(ethylenediamine)cobalt(III) base hydrolysis stereochemistry, J. Am. Chem. Soc. 90 (1968) 1468-1474.
18. 2 N,N') bis-(phenytoinato-κN)cobalt(II), Acta Crystallogr. E: Struct. Rep. Online 65 (2009) m1470.
19. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley, New Jersey, 2009.
20. 2], Inorg. Chem. 36 (1997) 2258-2266;
21. 4, J. Mol. Struct. 794 (2006) 341-347; (Pubitemid 44176029)
22. (c) D.A. House, J.W. Blunt, C-13 NMR as a technique for distinguishing between cis- and trans-dianionobis(ethylenediamine)cobalt(III) complexes, Inorg. Nucl. Chem. Lett. 11 (1975) 219-223.
23. (a) R.R. Fraser, K.E. Haque, Nuclear magnetic resonance and mass spectral properties of 5-aryltetrazoles, Can. J. Chem. 46 (17) (1968) 2855-2859;
24. (b) J. Ciarkowski, J. Kaczmarek, Z. Grzonka, A correlation of substituent effects with proton chemical shifts in aromatic tetrazolic acids, Org. Magn. Reson. 12 (11) (1979) 631-636.
25. R.P. Sharma, A. Singh, P. Brandão, V. Félix, P. Venugopalan, Syntheses, characterization, thermal properties and single crystal structure determination of cobalt(III) complexes with 2,2'-biimidazole and 1,10-phenanthroline ligands, Polyhedron 30 (2011) 2759-2767.
26. (a) C. Lee, W. Yang, R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B 37 (1988) 785-789;
27. (b) A.D. Becke, A new mixing of Hartree-Fock and local density-functional theories, J. Phys. Chem. 98 (1993) 1372-1377;
28. (c) A.D. Becke, D. Axel, Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys. 98 (1993) 5648-5652.
29. Gaussian 09, Revision A.1, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J.Normand,K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar,J.Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.
30. (a) G. Kresse, J. Hafner, Ab initio molecular dynamics for liquid metals, Phys. Rev. B 47 (1993) 558-561;
31. (b) G. Kresse, J. Hafner, Ab initio molecular-dynamics simulation of the liquid-metal-amorphous-semiconductor transition in germanium, Phys. Rev. B 49 (1994) 14251-14269;
32. (c) G. Kresse, D. Joubert, From ultrasoft pseudopotentials to the projector augmented-wave method, Phys. Rev. B 59 (1999) 1758-1775.
33. J.P. Perdew, J.A. Chevary, C. Fiolhais, Atoms, molecules, solids, and surfaces: applications of the generalized gradient approximation for exchange and correlation, Phys. Rev. B 46 (1992) 6671-6687.
34. S. Grimme, Semiempirical GGA-type density functional constructed with a long-range dispersion correction, J. Comput. Chem. 27 (2006) 1787-1799. (Pubitemid 44672561)