Abstract
Additive nature of the combined effect of the structure (X, Y substituents) and temperature on the rate and free activation energy has been established for the reactions of phenyloxirane with Y-substituted N-aroylbenzenesulfonamides catalyzed by X-substituted pyridines. The cross reaction series is isoenthalpic with respect to the structural effects. The mechanism of the catalytic process has been discussed.
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Bespalko, Y.N. and Shved, E.N., React. Kinet. Mech. Cat., 2019, vol. 126, no. 2, p. 903. https://doi.org/10.1007/s11144-018-01524-2
Deshpande, N., Parulkar, A., Joshi, R., Diep, B., Kulkarni, A., and Brunelli, N.A., J. Catal., 2019, vol. 370, p. 46. https://doi.org/10.1016/j.jcat.2018.11.038
Ly, U.Q., Pham M.-P., Marks, M.J., and Truong, T.N., J. Comput. Chem., 2017, vol. 38, no. 14, p. 1093. https://doi.org/10.1002/jcc.24779
Meninno, S. and Lattanzi, S., Chem. Eur. J., 2016, vol. 22, no. 11, p. 3632. https://doi.org/10.1002/chem.201504226.
Shpan’ko, I.V., Sadovaya, I.V., and Kulikova, N.V., Russ. J. Org. Chem., 2011, vol. 47, no. 5, p. 687. https://doi.org/10.1134/S107042801105006X
Shpan’ko, I.V. and Sadovaya, I.V., Kinet. Catal., 2014, vol. 55, no. 1, p. 56. https://doi.org/10.1134/S002315841401011X
Shpan’ko, I.V. and Sadovaya, I.V., Russ. J. Gen. Chem., 2016, vol. 86, no. 11, p. 2418. https://doi.org/10.1134/S1070363216110037
Shpan’ko, I.V. and Sadovaya, I.V., Theor. Exp. Chem., 2010, vol. 46, no. 3, p. 176. https://doi.org/10.1007/s11237-010-9136-z
Shpan’ko, I.V. and Sadovaya, I.V., Russ. J. Gen. Chem., 2017, vol. 87, no. 11, p. 2552. https://doi.org/10.1134/S107036321711007X
Palm, V.A., Fundamentals of the Quantitative Theory of Organic Reactions, Leningrad: Khimiya, 1977.
Liu, L. and Guo, Q.-X., Chem. Rev., 2001, vol. 101, no. 3, p. 673. https://doi.org/10.1021/cr990416z
Sharp, K., Protein Sci., 2001, vol. 10, no. 3, p. 661. https://doi.org/10.1110/ps.37801
Cornish-Bowden, A., J. Biosci., 2002, vol. 27, no. 2, p. 121. https://doi.org/10.1007/BF02703768
Starikov, E.B. and Norden, B., J. Phys. Chem. (B), 2007, vol. 111, no. 51, p. 14431. https://doi.org/10.1021/jp075784i
Parmon, V.N., React. Kinet. Mech. Cat., 2016, vol. 118, no. 1, p. 165. https://doi.org/10.1007/s11144-016-1005-x
Zuniga-Hansen, N., Silbert, L.E., and Calbi, M.M., Phys. Rev. (E), 2018, vol. 98, no. 3, p. 032128. https://doi.org/10.1103/PhysRevE.98.032128
Shpan’ko, I.V. and Sadovaya, I.V., Ukr. Khim. Zh., 2004, vol. 70, no. 4, p. 104.
Shpan’ko, I.V. and Sadovaya, I.V., Ukr. Khim. Zh., 2015, vol. 81, no. 10, p. 124.
Dneprovskii, A.S. and Temnikova, T.I., Teoreticheskie osnovy organicheskoi khimii (Theoretical Foundations of Organic Chemistry), Leningrad: Khimiya, 1991.
Derkach, G.I., Dregval’, G.F., and Kirsanov, A.V., Zh. Obshch. Khim., 1960, vol. 30, no. 10, p. 3402.
Shpan’ko, I.V., Sadovaya, I.V., and Kitaigorodskii, A.M., Ukr. Khim. Zh., 2003, vol. 69, no. 6, p. 111.
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Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 12, pp. 1835–1841.
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Shpanko, I.V., Sadovaya, I.V. Isoenthalpy Catalytic Effects of Pyridines in Reactions of Phenyloxyrane with N-Aroylbenzenesulfonamides. Russ J Gen Chem 89, 2358–2363 (2019). https://doi.org/10.1134/S1070363219120053
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DOI: https://doi.org/10.1134/S1070363219120053