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Russian Chemical Reviews, 1979, Volume 48, Issue 9, Pages 854–867
DOI: https://doi.org/10.1070/RC1979v048n09ABEH002417
(Mi rcr3164)
 

This article is cited in 38 scientific papers (total in 38 papers)

Hydrogen Bonds and the Reactivity of Organic Compounds in Proton Transfer and Nucleophilic Substitution Reactions

L. M. Epshtein

A. N. Nesmeyanov Institute of Organoelement Compounds, USSR Academy of Sciences, Moscow
Abstract: Recent data on various relations between the characteristics (spectroscopic and thermodynamic) of hydrogen bonds in different classes of organic compounds and the acid–base properties of the latter are examined. The principal approaches to the study of the influence of hydrogen bonds on acid–base equilibria in various solvents are demonstrated. Fundamentally new results, obtained in combined studies of proton transfer reactions in the gas phase and in solution, are analysed and approaches to allowance for the influence of hydrogen bonds on the reactants and the transition state in nucleophilic substitution reactions as well as the role of hydrogen bonds in the alteration of the rates and modes of chemical reactions are discussed.
The bibliography includes 152 references.
Bibliographic databases:
Document Type: Article
UDC: 541.121; 541.127; 541.571
Language: English
Original paper language: Russian


Citation: L. M. Epshtein, “Hydrogen Bonds and the Reactivity of Organic Compounds in Proton Transfer and Nucleophilic Substitution Reactions”, Usp. Khim., 48:9 (1979), 1600–1624; Russian Chem. Reviews, 48:9 (1979), 854–867
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  • https://doi.org/10.1070/RC1979v048n09ABEH002417
  • https://www.mathnet.ru/eng/rcr/v48/i9/p1600
  • This publication is cited in the following 38 articles:
    1. Spyridon Koutsoukos, Julian Becker, Ana Dobre, Zhijie Fan, Farhana Othman, Frederik Philippi, Gavin J. Smith, Tom Welton, Nat Rev Methods Primers, 2:1 (2022)  crossref
    2. Serhii Tretiakov, Léon Witteman, Martin Lutz, Marc‐Etienne Moret, Angew Chem Int Ed, 60:17 (2021), 9618  crossref
    3. Serhii Tretiakov, Léon Witteman, Martin Lutz, Marc‐Etienne Moret, Angewandte Chemie, 133:17 (2021), 9704  crossref
    4. Christof Hannesschlaeger, Andreas Horner, Peter Pohl, Chem. Rev., 119:9 (2019), 5922  crossref
    5. M. P. Pasechnik, A. G. Matveeva, Z. S. Klemenkova, O. I. Artyushin, K. V. Tcarkova, N. A. Bondarenko, Russ J Gen Chem, 88:7 (2018), 1369  crossref
    6. Eduardo Martínez-González, Felipe J. González, José R. Ascenso, Paula M. Marcos, Carlos Frontana, J. Org. Chem., 81:15 (2016), 6329  crossref
    7. Christian Greve, Erik T. J. Nibbering, Henk Fidder, J. Phys. Chem. B, 117:49 (2013), 15843  crossref
    8. Boaz G. Oliveira, Regiane C. M. U. Araújo, J Mol Model, 18:6 (2012), 2845  crossref
    9. Daniel P. DeCollibus, Alexander Marin, Alexander K. Andrianov, Biomacromolecules, 11:8 (2010), 2033  crossref
    10. Solvents and Solvent Effects in Organic Chemistry, 2010, 587  crossref
    11. T.V. Kulik, N.A. Lipkovska, V.N. Barvinchenko, B.B. Palyanytsya, O.A. Kazakova, O.A. Dovbiy, V.K. Pogorelyi, Journal of Colloid and Interface Science, 339:1 (2009), 60  crossref
    12. Levinson F.S., Varganov R.V., Zakiev M.M., Shakirova I.M., Sheremetev A.B., Dmitriev D.E., Krivolapov D.B., Litvinov I.A., Sharafutdinova D.R., Efremov Yu.Ya., Mendeleev Commun., 18:6 (2008), 329–331  crossref  isi
    13. L. M. Antonik, A. G. Khabibulina, Russ J Gen Chem, 78:1 (2008), 123  crossref
    14. N. O. Mchedlov-Petrosyan, V. I. Kukhtik, S. I. Egorova, Russ J Gen Chem, 76:10 (2006), 1607  crossref
    15. I. A. Kuznetsova, M. N. Rodnikova, N. A. Chumaevskii, N. A. Minaeva, Russ. J. Inorg. Chem., 51:3 (2006), 504  crossref
    16. Irina Velikyan, Sandipta Acharya, Anna Trifonova, Andras Földesi, Jyoti Chattopadhyaya, J. Am. Chem. Soc., 123:12 (2001), 2893  crossref
    17. J. A. Kereselidze, Chem Heterocycl Compd, 35:6 (1999), 666  crossref
    18. Mary A. Reppy, Martin E. Cooper, Juston L. Smithers, Douglas L. Gin, J. Org. Chem., 64:11 (1999), 4191  crossref
    19. Ibon Alkorta, Nuria Campillo, Isabel Rozas, José Elguero, J. Org. Chem., 63:22 (1998), 7759  crossref
    20. Chip Nataro, Jiabi Chen, Robert J. Angelici, Inorg. Chem., 37:8 (1998), 1868  crossref
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