Abstract
Kinetics of N-chloromethylamine decomposition in an aqueous base medium and chloroform at different temperatures is studied. The decomposition of N-chloromethylamine is found to obey a second order equation in an aqueous base medium at an equimolar ratio of the reagents and a first order equation in chloroform with excess base. The activation energy of N-chloromethylamine decomposition in the both solvents is determined. A mechanism for the reaction is proposed. N-Chloromethylamine is shown to have approximately equal stability in these solvents within the studied temperature range.
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P. Kovacic, M. K. Lowery, and K. W. Field, Chem. Rev. 70, 639 (1970).
I. V. Koval’, Russ. J. Org. Chem. 34, 757 (1998).
A. N. Mirskova, T. I. Drozdova, G. G. Levkovskaya, and M. G. Voronkov, Russ. Chem. Rev. 58, 250 (1989).
W. H. Dennis, L. A. Hull, and D. H. Rosenblatt, Org. Chem. 32, 3783 (1967).
P. Kovacic and M. K. Lowery, Org. Chem. 34, 911 (1969).
J. M. Antelo, F. Arce, D. Casal, et al., Tetrahedron 45, 3955 (1989).
C. Grohmann, H. Wang, and F. Glorius, Org. Lett. 14, 656 (2012).
Ka-Ho Ng, Z. Zhou, and Wing-Yiu Yu, Chem. Commun. 49, 7031 (2013).
R. Cadoni, A. Porcheddu, G. Glacomelli, and L. de Luca, Org. Lett. 14, 5014 (2012).
R. Vanjari, T. Guntreddi, and K. N. Singh, Org. Lett. 15, 4908 (2013).
T. J. Barker and E. R. Jarvo, J. Am. Chem. Soc. 131, 15598 (2009).
J. M. Antelo, F. Arce, and M. Parajo, J. Phys. Org. Chem. 9, 447 (1996).
J. M. Antelo, F. Arce, M. C. Castro, et al., Int. J. Chem. Kinet. 27, 703 (1995).
R. Ohme, E. Schmitz, and P. Dolge, Chem. Ber. 99, 2104 (1966).
E. Schmitz, in Three-Membered Rings with Two Heteroatoms, Advances in Heterocyclic Chemistry, Vol. 24, Ed. by A. R. Katritzky (Academic, New York, San Francisco, Londo, 1979), p. 63.
V. V. Kuznetsov, N. N. Makhova, Yu. F. Strelenko, and L. I. Khmel’nitskii, Russ. Chem. Bull. 40, 2496 (1991).
V. V. Kuznetsov, N. N. Makhova, and L. I. Khmel’nitskii, Russ. Chem. Bull. 46, 1354 (1997).
N. N. Makhova, A. N. Mikhailyuk, V. V. Kuznetsov, et al., Mendeleev Commun., 182 (2000).
V. V. Kuznetsov, S. A. Kutepov, N. N. Makhova, K. A. Lyssenko, and D. E. Dmitriev, Russ. Chem. Bull. 52, 665 (2003).
V. V. Kuznetsov, N. N. Makhova, D. E. Dmitriev, et al., Mendeleev Commun., 116 (2005).
V. V. Kuznetsov, V. B. Ovchinnikova, V. P. Ananikov, and N. N. Makhova, Russ. Chem. Bull. 55, 2056 (2006).
N. N. Makhova, V. Yu. Petukhova, and V. V. Kuznetsov, ARKIVOC B, 128 (2008).
V. A. Shapovalova, Pharmaceutical Analysis of Drugs (Rubikon, Kharkov, 1995), p. 111 [in Russian].
T. Yoshitomo, WO Patent No. 2014069668 (2014).
H. Bock and R. Dammel, Chem. Ber. 120, 1961 (1987).
J.-C. Guillemin and J.-M. Denis, Tetrahedron 44, 4431 (1988).
V. V. Kuznetsov, J. S. Syroeshkina, D. I. Moskvin, et al., J. Heterocycl. Chem. 45, 497 (2008).
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Original Russian Text © V.V. Kuznetsov, M.D. Vedenyapina, M.I. Pleshchev, S.B. Gashev, N.N. Makhova, A.A. Vedenyapin, 2016, published in Zhurnal Fizicheskoi Khimii, 2016, Vol. 90, No. 3, pp. 350–354.
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Kuznetsov, V.V., Vedenyapina, M.D., Pleshchev, M.I. et al. Kinetics and mechanism of N-chloromethylamine decomposition in solutions. Russ. J. Phys. Chem. 90, 541–544 (2016). https://doi.org/10.1134/S0036024416030225
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DOI: https://doi.org/10.1134/S0036024416030225