Conclusions
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1.
Electron-donor substituants in an aryl radical of symmetric diaryltriazenes (DAT's) accelerate the prototropic process in these compounds, while electron-acceptor substituents have the opposite effect.
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2.
In solutions of DAT's prototropic transfer is realized according to a bimolecular mechanism with the formation of a cyclic transition state with delocalized bonds in THF and according to an intramolecular mechanism with the formation of solvated ion pairs in Py.
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D. N. Kravtsov, A. N. Nesmeyanov, L. A. Fedorov, é. I. Fedin, A. S. Peregudov, E. V. Borisov, P. O. Okulevich, and S. A. Postovoi, Dokl. Akad. Nauk SSSR,242, 347 (1978).
A. N. Nesmeyanov, E. V. Borisov, A. S. Peregudov, D. N. Kravtsov, L. A. Fedorov, é. I. Fedin, and S. A. Postovoi, Dokl. Akad. Nauk SSSR,247, 1154 (1979).
G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley, New York (1972).
N. P. Marullo, C. B. Mayfield, and E. H. Wagener, J. Am. Chem. Soc.,90, 510 (1968).
L. A. Yanovskaya, Modern Theoretical Principles of Organic Chemistry [in Russian], Khimiya (1978), pp. 104–106.
L. Hunter, J. Chem. Soc.,1937, 320.
Z. Beneš, V. Beranek, J. Zimprich, and P. Vetešnic, Collect. Czech. Chem. Commun.,42, 702 (1977).
I. P. Gragerov, V. K. Pogorelyi, and I. F. Franchuk, Hydrogen Bonding and Fast Organic Exchange [in Russian], Naukova Dumka, Kiev (1978), p. 206.
P. K. Glasoe, S. Halloer, M. Hose, and J. M. Duke, Spectrochim. Acta,27A, 2309 (1971).
V. Zverina, M. Remes, J. Divis, J. Marhold, and M. Matrika, Collect. Czech. Chem. Commun.,38, 251 (1973).
P. Miles and H. Suschitzky, Tetrahedron,19, 385 (1963).
J. C. Earl, Chem. Ind.,1936, 192.
I. I. Arnold, Phys. Rev.,102, 136 (1956).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 110–116, January, 1981.
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Nesmeyanov, A.N., Borisov, E.V., Kravtsov, D.N. et al. Influence of the nature of the substituents and the medium on the mechanism and rate of proton transfer in diaryltriazenes. Russ Chem Bull 30, 89–94 (1981). https://doi.org/10.1007/BF00962260
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DOI: https://doi.org/10.1007/BF00962260