Abstract
Dimeric porphyrin(2,6-bis[15′-(3″,5″-di-tert-butylphenol)-3′,7′,13′,17′-tetramethyl-2′,8′,12′,18-tetraethylporphin-5′-yl]-4-tert-buthylphenol) and its binuclear zinc complex were obtained from 4,4′-dimethyl-3,3′-diethyldipyrrolylmethane, 2,6-diformyl-4-tert-butylphenol and 3,5-di-tert-buthylbenzaldehyde. Coordina-tion properties of dimeric zincporphyrin in the intermolecular reaction with nitrogen-containing bases (imidazole, 2-methylimidazole, and pyridine) in benzene were studied. Geometry and electronic structure of the zincporphyrin and its molecular complexes were calculated by a quantum-chemical method. Energy characteristics of the intermolecular reaction of the dimeric zincporphyrin with bases were determined. The calculated energies of the central metal atom interaction with the nitrogen atom of an extra-ligand agree well with the stability of the Zn-porphyrin molecular complexes. The influence of the deformation distortions of the porphyrin ligand on the strength of the metal-extra-ligand σ-bond was established.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Askarov, K.A., Berezin, B.D., and Evstigneev, R.P., Porfiriny: struktura, svoistva, sintez (Porphyrins: Structure, Properties, Synthesis), Enikolopyan, N.S., Ed., Moscow: Nauka, 1985.
Scheidt, W.R., Porphyrin Stereochemistry. The Porphyrins, Dolphin, D., Ed., New York: Acad. Press, 1979, vol. 3, Ch. 10, p. 463.
Scheidt, W.R. and Lee, Y.J., Struct. Bonding, Berlin:: 1987, vol. 64, p. 1.
Wickramasinghe, A., Jaquinod, L., Nurco, D.J., and Smith, K.M., Tetrahedron, 2001, vol. 57, p. 4261.
Bulatov, M.I. and Kalinkin, I.P., Prakticheskoe rukovodstvo po fotokolorimetricheskim i spektrofotometricheskim metodam analiza (Manual on Photo-colorimetric and Spectrophotometric Methods of Analysis), Leningrad: Khimiya, 1968.
Zaitseva, S.V., Zdanovich, S.A., and Koifman, O.I., Koord. Khim., 2006, vol. 32, no. 7, p. 54.
Zaitseva, S.V., Zdanovich, S.A., Ageeva, T.A., Golubcikov, O.A., and Semeikin, A.S., Koord. Khim., 2001, vol. 27, no. 3, p. 168.
Zaitseva, S.V., Cand. Sci. (Chem.) Dissertation, Ivanovo, 1999.
Karmanova, T.V., Koifman, O.I., and Berezin, B.D., Koord. Khim., 1983, vol. 9, no. 6, p. 772.
Tipugina, M.Yu., Lomova, T.N., and Ageeva, T.A., Zh. Obshch. Khim., 1999, vol. 69, no. 3, p. 459.
Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, p. 209.
Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, p. 221.
Stewart, J.J.P., J. Computer-Aided Molecular Desing, 1990, vol. 4, p. 1.
Fletcher, R., Methods of Optimization, New York: J. Wiley, 1980, p. 45.
Treibs, A. and Haberle, N., Liebigs Ann., 1968, vol. 718, p. 183.
Mamardashvili, N.Z., Semeikin, A.S., and Golubchikov, O.A., Zh. Org. Khim., 1993, vol. 29, no. 6, p. 1213.
Mamardashvili, N.Zh., Semeikin, A.S., Berezin, B.D., and Golubchikov, O.A., USSR Inventor’s Certificate no. 1671665, 1991, Byul. Izobret., 1991.
Tablitsy constant skorostei i ravnovesii gomoliticheskikh organicheskikh reaktsii (Tables of Rate Constants and Equilibria of Homolytic Organic Reactions), Moscow: Viniti, 1976, vol. 2.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © S.V. Zaitseva, S.A. Zdanovich, A.S. Semeikin, O.I. Koifman, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 3, pp. 508–517.
Rights and permissions
About this article
Cite this article
Zaitseva, S.V., Zdanovich, S.A., Semeikin, A.S. et al. Synthesis and coordination properties of the zinc complex of dimeric porphyrin in reactions with imidazole, 2-methylimidazole, and the pyridine in benzene. Russ J Gen Chem 78, 493–502 (2008). https://doi.org/10.1134/S1070363208030250
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363208030250