Abstract
Main concepts of the Shilov–Ostwald theory of conjugate chemical reactions are analyzed from the standpoint of complex reaction kinetics, theory of reaction routes, and thermodynamics of irreversible processes. Classification of conjugate reactions and an algorithm of catalytic system design for conducting these processes are proposed.
Similar content being viewed by others
References
Shilov, N.A., Osopryazhennykh reaktsiyakh okisleniya (Conjugate Oxidation Reactions), Moscow: Tipografiya Mamontova, 1905.
Nagiev, T.M., Khimicheskoe sopryazhenie (Chemical Conjugation), Moscow: Nauka, 1989.
Nagiev, T.M., Mater. Sci. Appl., 2015, vol. 6, p. 152.
Nagiev, T.M., Vzaimodeistvie sinkhronnykh reaktsii v khimii i biologii (Interaction of Synchronous Reactions in Cnemistry and Biology), Baku: ELM, 2001.
Catalytic Asymmetric Conjugate Reactions, Cordova, A., Ed., Weinheim: Wiley–VCH, 2010.
Kessler, F., Poggendorff’s Ann., 1855, vol. 95, p. 224.
Khimicheskaya entsiklopediya (Encyclopedia of Chemistry), Moscow: Bol’shaya Rossiiskaya Entsiklopediya, 1995, vol. 4, p. 768.
Emanuel’, N.M. and Knorre, D.G., Kurs khimicheskoi kinetiki (Chemical Kinetics), Moscow: Khimiya, 1974.
Zelinski, N.D. and Pavlov, G.S., Berichte, 1933, vol. 66, p. 1420.
Gryaznov, V.M. and Smirnov, V.S., Dva protsessa v odnom reaktore (Two Processes in One Reactor), Moscow: Znanie, 1972.
Gryaznov, V.M., Smirnov, V.S., and Ivanova, L.K., Vestn. Akad. Nauk SSSR, 1971, no. 7, p. 142.
Vsesvyatskaya, N.Yu., Bruk, L.G., Stromnova, T.A., Alekseeva, N.F., and Temkin, O.N., Zh. Org. Khim., 1978, vol. 14, p. 473.
Moiseev, I.I., Vargaftik, M.N., Gentosh, O.N., Zhavoronkov, M.N., Pazderskii, Yu.A., Kalechits, I.V, Stromnova, T.A., and Shcherbakova, L.S., Dokl. Akad. Nauk SSSR, 1977, vol. 237, p. 645.
Stromnova, T.A., Vargaftik, M.N., and Moiseev, I.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1983, no. 1, p. 31.
De Donder, T. and van Rysselberghe, P., Affinity, Menlo Park, Calif.: Stanford Univ. Press, 1936.
Boudart, M., J. Phys Chem, 1983, vol. 87, p. 2786.
Krylov, O.V., Kinet. Katal., 1985, vol. 26, no. 2, p. 263.
Temkin, O.N., Homogeneous Catalysis with Metal Complexes: Kinetic Aspects and Mechanisms, Chichester, UK: Wiley, 2012.
Bazhin, N.M., Ivanchenko, V.A., and Parmon, V.N., Termodinamika dlya khimikov (Thermodynamics for Chemists), Moscow: Khimiya, KoloSS, 2004.
Lehninger, A.L., Biochemistry: The Molecular Basis of Cell Structure and Function, New York: Worth, 1972.
Christiansen, J.A., Adv. Catal., 1953, vol. 5, p. 311.
Fujiwara, Y., Takaki, K., and Takiguchi, Y., Synlett, 1996, p. 591.
Aoyama, Y., Tanaka, Y., Fujisawa, T., Watanabe, T., Toi, H., and Ogoshi, H., J. Org. Chem., 1987, vol. 52, p. 2555.
Yamado, N., Takai, T., Rhode, O., and Mukaiyama, T., Chem. Lett., 1991, p. 1.
Lin, Y., Murata, K., and Inaba, M., Chem. Commun., 2004, p. 582.
Abdullaeva, A.S., Griva, E.A., Oshanina, I.V., Bruk, L.G., and Temkin, O.N., Tezisy dokl. VI Ross. konf. “Mekhanizmy kataliticheskikh reaktsii” (Proc. VI Russian Conf. on Mechanisms of Catalytic Reactions), Moscow, 2002, vol. 2, p. 44.
Abdullaeva, A.S., Cand. Sci. (Chem.) Dissertation, Moscow: Moscow Inst. of Fine Chemical Technology, 2005.
Zudin, V.N., Likholobov, V.A., and Ermakov, Yu.I., Kinet. Katal., 1979, vol. 20, p. 1559.
Inoki, S., Kato, K., Takai, T., Isayama, S., Yamada, T., and Mukaiyama, T., Chem. Lett., 1989, p. 515.
Korol’kov, D.V. and Shchukarev, A.V., Vestn. SPbGU, Ser. 4: Phys., Chem., 1992, no. 4, p. 34.
Korol’kov, D.V., Teoreticheskaya khimiya (Theoretical Chemistry), vol. 1: Obshchie printsipy i kontseptsii (General Principles and Conceptions), Moscow: Akademkniga, 2007.
Beckett, M.A., Inorg. Chim. Acta, 1989, vol. 157, p. 171.
Goldman, A.S., Roy, A.H., Huang, Z., Ahuya, R., Schinski, W., and Brookhart, M., Science, 2006, vol. 312, p. 257.
Kuklin, S.A., Sheloumov, A.M., Dolgushin, F.M., Ezernitskaya, M.G., Peregudov, A.S., Petrovskii, P.V., and Koridze, A.A., Organometallics, 2006, vol. 25, no. 22, p. 5466.
Choi, J., MacArthur, A.H.R., Brookhart, M., and Goldman, A.S., Chem. Rev., 2011, vol. 111, no. 3, p. 1761.
Bobolev, A.V., Blyumberg, E.A., Norikov, Yu.D., and Emanuel’, N.M., Zh. Fiz. Khim., 1970, vol. 44, no. 1, p. 1028.
Skibida, I.P., Usp. Khim., 1975, vol. 44, no. 10, p. 1729.
Denisov, E.T., Sarkisov, O.P., and Likhtenshtein, G.I., Khimicheskaya kinetika (Chemical Kinetics), Moscow: Khimiya, 2000.
Temkin, O.N., Kinet. Catal., 2012, vol. 53, no. 3, p. 313.
Moiseev, I.I. and Pestrikov, S.V., Dokl. Akad. Nauk SSSR, 1966, vol. 171, p. 151.
Pestrikov, S.V., Moiseev, I.I., and Sverzh, L.M., Kinet. Katal., 1969, vol. 10, p. 74.
Bruk, L.G., Temkin, O.N., Goncharova, Z.V., Ustenko, I.S., and Flid, V.R., React. Kinet. Catal. Lett., 1978, vol. 9, no. 3, p. 303.
Shindoh, N., Takemoto, Y., and Takasu, K., Chem. Eur. J., 2009, vol. 15, p. 12168.
Ajamian, A. and Gleason, J.L., Angew. Chem., 2004, vol. 116, p. 3842.
Fogg, D.E. and Santos, E.N., Coord. Chem. Rev., 2004, vol. 248, p. 2365.
Multicomponent Reactions, Zhu, J. and Bienayme, H., Eds., Weinheim: Wiley–VCH, 2005.
Wasilke, J.C., Obrey, S.J., Baler, R.T., and Bazan, G.C., Chem. Rev., 2005, vol. 105, p. 1001.
Tietze, L.F., Brasche, G., and Gericke, K.M., Domino Reactions in Organic Chemistry, Weinheim: Wiley–VCH, 2007.
Bruk L.G., Oshanina I.V., Gorodskii S.N., and Temkin O.N., Ross. Khim. Zh., 2006, vol. 50, no. 11, p. 103.
Parmon, V.N., Thermodinamics of Non-Equilibrium Processes for Chemists with a Particular Application to Catalysis, Amsterdam: Elsevier, 2010.
Kiperman, S.L., Osnovy khimicheskoi kinetiki v geterogennom katalize (Principles of Chemical Kinetics in Heterogeneous Catalysis), Moscow: Khimiya, 1979.
Prigogine, I. and Defay, R., Chemical Thermodynamics, London: Longmans, 1954.
Kondepudi, D. and Prigogine, I., Modern Thermodynamics: From Heat Engines to Dissipative Systems, Chichester, UK: Wiley, 1998.
Bruk, L.G., Flid, V.R., Belova, T.B., and Temkin, O.N., in Khimicheskaya kinetika v katalize: Kineticheskie modeli zhidkofaznykh reaktsii (Chemical Kinetics in Catalysis: Kinetic Models of Liquid-Phase Reactions), Chernogolovka, Moscow oblast: Inst. Probl. Khim. Fiz., 1985, p. 120.
Bruk, L.G., Doctoral (Chem.) Dissertation, Moscow: Moscow Inst. of Fine Chemical Technology, 1996.
Bruk, L.G., Oshanina, I.V., Kozlova, A.P., and Temkin, O.N., J. Mol. Catal. A: Chem., 1995, vol. 104, p. 9.
Bruk, L.G., Oshanina, I.V., Kozlova, A.P., Temkin, O.N., and Odintsov, K.Yu., Russ. Chem. Bull., 1998, vol. 47, no. 6, p. 1071.
Temkin, O.N., Bruk, L.G., and Bonchev, D., Teor. Eksp. Khim., 1988, no. 3, p. 282.
Moiseev, I.I., p-Kompleksy v zhidkofaznom okislenii olefinov (p-Complexes in Liquid-Phase Olefin Oxidations), Moscow: Nauka, 1970.
Zudin, V.N., Likholobov, V.A., and Ermakov, Yu.I., Kinet. Katal., 1979, vol. 20, no. 3, p. 805.
Zudin, V.N., Chinakov, V.D., Nekipelov, V.M., Likholobov, V.A., and Yermakov, Y.I., J. Organomet. Chem., 1985, vol. 289, no. 3, p. 425.
Zudin, V.N., Chinakov, V.D., Nekipelov, V.M., Rogov, V.A., Likholobov, V.A., and Yermakov, Y.I., J. Mol. Catal., 1989, vol. 52, no. 1, p. 27.
Danilyuk, A.F., Likholobov, V.A., and Ermakov, Yu.I., Kinet. Katal., 1977, vol. 18, no. 1, p. 252.
Likholobov, V.A. and Ermakov, Yu.I., Kinet. Katal., 1980, vol. 21, no. 4, p. 904.
Bianchi, D., Bortolo, R., D’Aloisio, R., and Rocci, M., J. Mol. Catal. A: Chem., 1999, vol. 150, p. 87.
Cavinato, G. and Toniolo, L., J. Mol. Catal., 1981, vol. 10, no. 2, p. 161.
Petrov, E.S. and Noskov, Yu.G., Ross. Khim. Zh., 1998, vol. 42, no. 4, p. 149.
Bruk, L.G., Temkin, O.N., Abdullaeva, A.S., Timashova, E.A., Bukina, E.Yu., Odintsov, K.Yu., and Oshanina, I.V., Kinet. Catal., 2010, vol. 51, no. 5, p. 678.
Putin, A.Yu., Bukina, E.Yu., Katsman, E.A., Trunilina, K.V., Oshanina, I.V., Bruk, L.G., and Temkin, O.N., Russ. J. Phys. Chem. A, 2013, vol. 87, no. 3, p. 465.
Timashova E.A., Putin A.Yu., Bychkova E.Yu., Bruk L.G., Temkin O.N., and Oshanina, I.V., Vestn. MITKhT, 2014, vol. 9, no. 3, p. 57.
Putin, A.Yu., Bychkova, E.Yu., Trunilina, K.V., Zakgeim, A.Yu., Katsman, E.A., Shishilov, O.N., Akhmadulina, N.S., Oshanina, I.V., Temkin, O.N., and Bruk, L.G., Russ. J. Phys. Chem. A, 2015, vol. 89, no. 3, p. 359.
Smit, W.A. Bochkov, A.F., and Caple, R., Organic Synthesis: The Science behind the Art, London: The Royal Society of Chemistry, 1998.
Zeigarnik, A.V., Bruk, L.G., Temkin, O.N., Likholobov, V.A., and Maier, L.I., Russ. Chem. Rev., 1996, vol. 65, no. 2, p. 117.
Shalgunov, S.I., Zeigarnik, A.V., Bruk, L.G., and Temkin, O.N., Russ. Chem. Bull., 1999, vol. 48, no. 10, p. 1867.
Dong, G., Teo, P., Wickens, K., and Grubbs, R.H., Science, 2011, vol. 333, no. 6049, p. 1609.
Hayashi, T., Tanaka, K., and Haruta, M., J. Catal., 1998, vol. 178, p. 566.
Sinha, A.K., Seelan, S., Tsubota, S., and Haruta, M., Angew. Chem., Int. Ed. Engl., 2004, vol. 43, p. 1546.
Chowdhury, B., Bravo-Suárez, J.J., Date, M., Tsubota, S., and Haruta, M., Angew. Chem., Int. Ed. Engl., 2006, vol. 45, p. 412.
Taylor, B., Lauterbach, J., and Delgass, W.N., Appl. Catal., A, 2005, vol. 291, p. 188.
Cumaranatunge, L. and Delgass, W.N., J. Catal., 2005, vol. 232, p. 38.
Bravo-Suárez, J.J., Bando, K.K., Lu, J., Haruta, M., Fujitani, T., and Oyama, S.T., J. Phys. Chem., 2008, vol. 112, p. 1115.
Lu, J.Q., Zhang, X., Bravo-Suárez, J.J., Tsubota, S., Gaudet, J., and Oyama, S.T., Catal. Today, 2007, vol. 123, p. 189.
Sobolev, V.I. and Koltunov, K.Y., Catal. Commun., 2013, vol. 40, p. 103.
Chepaikin, E.G. and Borshch, V.N., J. Organomet. Chem., 2015, vol. 793, p. 78.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © L.G. Bruk, O.N. Temkin, 2016, published in Kinetika i Kataliz, 2016, Vol. 57, No. 3, pp. 275–296.
Rights and permissions
About this article
Cite this article
Bruk, L.G., Temkin, O.N. Conjugate reactions: New potentials of an old idea. Kinet Catal 57, 277–296 (2016). https://doi.org/10.1134/S0023158416030022
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0023158416030022