Abstract
Reaction of nickel 5,15-di(o-methoxyphenyl)-2,8,12,18-tetramethyl-3,7,13,17-tetrabutylporphyrinate and 5,10,15,20-tetraphenylporphyrinate with dicumene peroxide in benzene at 295 K was investigated by spectrophotometric method. Kinetic parameters of the reaction were determined, and mechanism of the studied process was suggested. Comparative analysis of the oxidative and reductive properties of nickel porphyrinates in reaction with dicumene peroxide was accomplished. Effect of the electronic and conformation factors on the reaction kinetics was shown. The theoretical calculation of the geometric parameters of the reagents and intermediates of the reaction was performed by PM3 quantum-chemical method.
Similar content being viewed by others
References
Koifman, O.I. and Mamardashvili, N.Zh., Ross. Nanotechnol., 2009, vol. 4, nos. 5–6, p. 59.
Koifman, O.I., Ageeva, T.A., and Nikolaeva, O.I., Izv. Vuzov, Ser. Khim. Technol., 2004, vol. 47, no. 5, p. 91.
Beletskaya, I.P., Tyurin, V.S., Tsivadze, A.Y., Guilard, R., and Stern, C., Chem. Rev., 2009, vol. 109, no. 5, p. 1659. DOI: 10.1021/cr800247a.
Yashchuk, Yu.P., Tyurin, V.S., and Beletskaya, I.P., Makrogeterotsykly, 2012, vol. 5, nos. 4–5, p. 302.
Milaeva, E.R., Gerasimova, O.A., Jingwei, Zhangt, Shpakovsky, D.B., Syrbu, S.A., Semeykin, A.S., Koifman, O.I., Kireeva, E.G., Shevtsova, E.F., Bachurin, S.J., and Zefirov, N.S., J. Inorg. Biochem., 2008, vol. 102, p. 1348. DOI: 10.1016/j.jinorgbio.2008.01.022.
Lomova, T.N., Motorina, E.V., Ovchenkova, E.N., and Klyueva, M.E., Russ. Chem. Bull., 2007, vol. 56, no. 4, p. 660. DOI: 10.1007/s11172-007-0105-1.
Afanasiev, P., Millet, J.-M.M., Bouchu, D., Kudrik, E.V., and Sorokin A.B., Dalton Trans., 2011, vol. 40, p. 701. DOI: 10.1039/C0DT00958J.
Afanasiev, P., Bouchu, D., Kudrik, E.V., Millet, J.-M.M., and Sorokin A.B., Dalton Trans., 2009, p. 9828.
Zaitseva, S.V., Zdanovich, S.A., and Koifman, O.I., Russ. J. Gen. Chem., 2005, vol. 75, no. 5, p. 800. DOI: 1007/s11176-005-0321-z.
Simonova, O.R., Zaitseva, S.V., and Koifman, O.I., Russ. J. Gen. Chem., 2008, vol. 78, no. 6, p. 1260. DOI: 10.1134/S1070363208060285.
Simonova, O.R., Zaitseva, S.V., and Koifman, O.I., Russ. J. Coord. Chem., 2009, vol. 35, no. 5, p. 320. DOI: 10.1134/S1070328409050029.
Lomova, T.N., Tyulyaeva, E.Y., and Klyueva, M.E., Russ. J. Phys. Chem. (A), 2011, vol. 85, no. 6, p. 926. DOI: 10.1134/S0036024411060215.
Bichan, N.G., Tyulyaeva, E.Yu. and Lomova, T.N., Makrogeterotsykly, 2013, vol. 6, no. 2, p. 144.
Thies, S., Bornholdt, C., Kohler, F., Sonnichsen, F.D., Nather, C., Tuczek, F., and Herges, R., Chem. Eur. J., 2010, vol. 16, p. 10074.
Cheremenskaya, O.V., Solov’eva, A.B., Ponomarev, G.V., and Timashev, S.F., Russ. J. Phys. Chem. (A), 2001, vol. 75, no. 10, p. 1633.
Zaitseva, S.V., Zdanovich, S.A., and Golubchikov, O.A., Russ. J. Coord. Chem., 2002, vol. 28, no. 12, p. 843.
Simonova, O.R., Zaitseva, S.V., and Koifman, O.I., Russ. J. Gen. Chem., 2013, vol. 83, no. 1, p. 110. DOI: 10.1134/S1070363213010192.
Schidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., and Montgomeri, J.A., J. Comput. Chem., 1993, vol. 14, no. 11, p. 1347. DOI: 10.1002/jcc.540141112.
Stewart, J.J.P., J. Computer-Aided Mol. Design, 1990, vol. 4, p. 1. DOI: 10.1007/BF00128336.
Fletcher, R. Methods of Optimization. New York: John Wiley & Sons, 1980.
Eksperimental’nye metody khimicheskoi kinetiki (Experimental Methods of Chemical Kinetis), Emanuel’, N.M. and Sergeev, G.B., Eds., Moscow: Vysshaya Shkola, 1980.
Lindsey, J.S. and Woodford, J.N., Inorg. Chem., 1995, no. 34, p. 1063. DOI: 1021/ic00109a011.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © O.P. Simonova, S.V. Zaitseva, O.I. Koifman, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 12, pp. 2012–2019.
Rights and permissions
About this article
Cite this article
Simonova, O.P., Zaitseva, S.V. & Koifman, O.I. Kinetics of reaction between nickel porphyrinates and dicumene peroxide. Russ J Gen Chem 84, 2429–2435 (2014). https://doi.org/10.1134/S1070363214120135
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363214120135