EFFECT OF ASSOCIATION ON NUCLEOPHILIC ADDITION
645
Compd., 1998, vol. 370, no. 4, p. 547. doi 10.1002/
chin.199841152
Steric and inductive effects of the substituents at
nitrogen atom in the molecules of tertiary amines 4–6
were characterized by parameters ΣRS and Σσ*
calculated from Eqs. (4) and (5) using the Galkin–
Cherkasov method [22, 23].
8. Kazantsev, O.A., Kazakov, S.A., Shirshin, K.V., and
Danov, S.M., Russ. J. Org. Chem., 2000, vol. 36, no. 3,
p. 343. doi 10.1002/chin.200051078
9. Shirshin, K.V., Kazantsev, O.A., Kazakov, S.A., and
Danov, S.M., J. Appl. Chem., 1999, vol. 72, no. 2,
p. 278.
10. Kazantsev, O.A., Baruta, D.S., Shirshin, K.V., Sivo-
khin, A.P., and Kamorin, D.M., Russ. J. Phys. Chem.,
2010, vol. 84, no. 12, p. 2071. doi 10.1134/
s0036024410120113
(σA)i
n
σ* = Σ –—— ,
(4)
(5)
ri2
i=1
Ri2
RS = 30log 1 – nΣ —— .
4ri2
i=1
11. Kazantsev, O.A., Baruta, D.S., Shirshin, K.V., Sivo-
khin, A.P., and Kamorin, D.M., Russ. J. Phys. Chem.,
2011, vol. 85, no. 3, p. 413. doi 10.1134/
s0036024411030162
12. Kazantsev, O.A., Shirshin, K.V., Kazakov, S.A., and
Danov, S.M., Zh. Obshch. Khim., 1996, vol. 66, no. 12,
p. 2014.
13. Suminov, S.I. and Kost, A.N., Russ. Chem. Rev., 1969,
vol. 38, no. 11, p. 1933. doi 10.1070/
rc1969v038n11abeh001860
where (σА)i denotes the ability of the ith atom of the
substituent to manifestation of inductive effect (by the
Taft’s scale of inductive constants; inductive effect of
alkyl substituents was taken to be zero), Ri is the
covalent radius of the ith atom, Å, ri is the distance of
the ith atom from the reaction center, Å.
ACKNOWLEDGMENTS
14. Le Berre, A. and Delacroix, A., Bull. Soc. Chim. Fr.,
1973, vols. 7–8, p. 2404.
15. Shirshin, K.V., Kazantsev, O.A., and Sivokhin A.P.,
Plastmassy, 2009, no. 11, p. 14.
16. Bondarenko S.P., Tiger R.P., and Jentelis, S.G., Zh. Fiz.
Khim., 1981, vol. 55, no. 7, p. 1716.
This work was performed with the financial support
from the Ministry of Education and Science (State
contract 10.2326.2017/PCh) and the Program of
development of R.E. Alekseev Nizhny Novgorod State
Technical University.
17. Stul’, B.Ya. and Chesnokov, B.B., Kinet. Catal., 2002,
REFERENCES
vol. 43, no. 5, p. 741. doi 10.1023/a:1020620500591
18. Kulagina, T.P. and Smirnov, L.P., Doklady Chem.,
2009, vol. 427, no. 2, p. 136. doi 10.1134/
s0012501609080028
1. Yang, J., Curr. Opinion Colloid Interface Sci., 2002,
vol. 7, p. 276. doi 10.1016/S1359-0294(02)00071-7
2. Gui, Z., Qian, J., An, Q., Xu, H., and Zhao, Q., Eur.
Polym. J., 2009, vol. 45, no. 5, p. 1403. doi 10.1016/
j.eurpolymj.2009.02.010
19. Kabanov, V.A. and Topchiev, D.A., Polimerizatsiya
ionizuyushchikhsya monomerov (Polymerization of
Ionizing Monomers), Мoscow: Nauka, 1975.
3. Hoover, M.F., J. Macromol. Sci. (A), 1970, vol. 4, no. 6,
20. Kolomeitseva, O.P. and Kuznetsova, N.N., Zh. Prikl.
Khim., 1972, vol. 45, p. 1978.
p. 1327. doi 10.1080/00222337008081733
4. Sadiku, E., J. Appl. Pol. Sci., 2006, vol. 102, no. 1,
21. Shirshin, K.V., Kazantsev, O.A., Zil’berman, E.N.,
Salov, V.N., and Molotkov, V.A., Zh. Prikl. Khim.,
1990, vol. 63, no. 12, p. 1978.
22. Galkin, V.I., Cherkasov, A.R., Sayakhov, R.D., and
Cherkasov, R.A., Russ. J. Gen. Chem., 1995, vol. 65,
no. 3, p. 404.
23. Sayakhov, R.D., Cherkasov, R.A., and Galkin, V.I.,
Russ. Chem. Rev., 1991, vol. 60, no. 8, p. 815. doi
10.1070/rc1991v060n08abeh001113
p. 166. doi 10.1002/app.23407
5. Shachat, N., Haggard, R.A., and Lewis, S.N., USA
Patent 3689470A, 1972.
6. Kazantsev, O.A., Zil’berman, E.N., Salov, V.N., and
Krasnov, V.L., Zh. Prikl. Khim, 1987, vol. 60, no. 9,
p. 2142.
7. Kazantsev, O.A., Kazakov, S.A., Shirshin, K.V., Da-
nov, S.M., and Krasnov, V.L., Chem. Heterocycl.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 4 2018