Abstract
Data are surveyed on cross correlations for nucleophilic substitution at benzoyl, benzyl, and benzhydryl carbon atoms. The cross correlation coefficients and isoparametric points are used to interpret the reaction mechanisms.
Similar content being viewed by others
References
Yu. N. Molin and I. V. Melikhov,Zh. Vsesoyus. Khim. Obshch. im. D. I. Mendeleeva,35, No. 2, 223–228 (1990).
V. A. Legasov and A. L. Buchachenko,Usp. Khim.,55, No. 12, 1949–1978 (1986).
A. I. Lesnikovich and S. V. Levchik,Correlations in Modern Chemistry [in Russian], Universitetskoe, Minsk (1989).
V. A. Pal'm,Principles of Quantitative Organic Reaction Theory [in Russian], Khimiya, Leningrad (1967).
V. A. Pal'm,Principles of Quantitative Organic Reaction Theory [in Russian], Khimiya, Leningrad (1977).
Yu. A. Zhdanov and V. I. Minkin,Correlation Analysis in Organic Chemistry [in Russian], Izd. Rostov Univ., Rostov-on-Don (1966).
J. E. Leffler and E. Grunwald,Rates and Equilibria of Organic Reactions, Wiley, New York and London (1963).
C. Hansch, A. Leo, and R. W. Taft,Chem. Rev.,91, No. 2, 165–195 (1991).
I. V. Trushkov, N. D. Chuvylkin, A. S. Koz'min, and N. S. Zefirov,Izv. Akad. Nauk, Ser. Khim., No. 5, 804–826 (1995).
J.-E. Dubois, M.-F. Ruasse, and A. Argile,J. Am. Chem. Soc.,106, No. 17, 4840–4845 (1984).
W. P. Jencks,Chem. Rev.,85, No. 6, 511–527 (1985).
I. Lee,Chem. Soc. Rev.,19, 317–333 (1990).
I. Lee,Adv. Phys. Org. Chem.,27, 57–117 (1992).
I. V. Shpan'ko,Mendeleev Commun., 119–120 (1991).
Ya. Kh. Riikoya, Kh. R. Timotkheus, and V. A. Pal'm,Reakts. Sposobnost' Org. Soedin.,14, No. 4, 522–540 (1977).
V. Palm, V. Timotheus, H. Pooga, et al.,Org. React.,30, No. 1, 69–72 (1996).
V. Palm and S. Kaasik,Org. React.,30, No. 1, 73–83 (1996).
B. V. Gidaspov, P. A. Ivanov, S. A. Pivovarov, and V. F. Selivanov,Reakts. Sposobnost' Org. Soedin.,8, No. 1, 49–61 (1971).
S. A. Pivovarov, V. F. Selivanov, and B. V. Gidaspov,Reakts. Sposobnost' Org. Soedin.,12, No. 2, 307–328 (1975).
S. A. Pivovarov, V. F. Selivanov, B. I. Istomin, and B. V. Gidaspov,Reakts. Sposobnost' Org. Soedin.,12, No. 2, 367–382 (1975).
V. A. Pal'm and B. I. Istomin,Reakts. Sposobnost' Org. Soedin.,6, No. 2, 427–437 (1969).
I. V. Shpanko, S. I. Kim, H. J. Koh, and I. Lee,Bull. Korean Chem. Soc.,16, No. 6, 533–538 (1995).
B. I. Istomin, S. A. Pivovarov, V. F. Selivanov, et al.,Reakts. Sposobnost' Org. Soedin.,12, No. 2, 289–300 (1975).
C. Johnson,Hammet's Equation [Russian translation], Mir, Moscow (1977).
D. J. McLennan,Tetrahedron,34, No. 15, 2331–2341 (1978).
I. V. Shpan'ko, G. D. Titskii, L. M. Litvinenko, and M. A. Eremeev,Reakts. Sposobnost' Org. Soedin.,10, No. 1, 187–202 (1973).
I. V. Shpan'ko, A. N. Goncharov, E. V. Chetverova, and E. E. Likhomanenko,Zh. Org. Khim.,22, No. 7, 1432–1438 (1986).
I. V. Shpan'ko, A. N. Goncharov, and L. M. Litvinenko,Zh. Org. Khim.,13, No. 4, 761–766 (1977).
G. D. Titskii, I. V. Shpan'ko, L. M. Litvinenko, and V. M. Shuliko,Reakts. Sposobnost' Org. Soedin.,8, No. 1, 39–47 (1971).
A. N. Goncharov, I. V. Shpan'ko, E. V. Chetverova, and E. E. Likhomanenko,Ukr. Khim. Zh.,52, No. 10, 1077–1082 (1986).
A. N. Goncharov, I. V. Shpan'ko, and A. P. Korostylev,Zh. Org. Khim.,17, No. 5, 972–978 (1981).
I. V. Shpanko,Org. React.,31, No. 1, 177–180 (1997).
I. V. Shpan'ko, L. M. Litvinenko, A. P. Korostylev, et al.,Dokl. Akad. Nauk SSSR,234, No. 6, 1358–1361 (1977).
I. M. Serebryakov, I. V. Shpanko, and N. M. Oleinik,Org. React.,28, No. 1, 6–11 (1993).
A. Pross,Adv. Phys. Org. Chem.,14, 69–132 (1977).
C. D. Johnson,Chem. Rev.,75, No. 6, 755–765 (1975).
M. Štrasak,Chem. Listy,76, No. 9, 911–943 (1982).
I. V. Shpan'ko and I. M. Serebryakov,Ukr. Khim. Zh.,60, No. 11, 793–796 (1994).
I. M. Serebryakov, N. M. Oleinik, and I. V. Shpanko,Org. React.,28, No. 1, 12–17 (1993).
I. V. Shpanko, I. M. Serebryakov, N. M. Oleinik, and B. V. Panchenko,Org. React.,30, No. 1, 3–6 (1996).
I. V. Shpanko and I. M. Serebryakov,Org. React.,30, No. 1, 7–11 (1996).
R. Schmid and V. N. Sapunov,Informal Kinetics [Russian translation], Mir, Moscow (1985).
Additional information
Donetsk State University, 24 Universitetskaya ul., Donetsk 340055, Ukraine. Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 35, No. 2, pp. 67–78, March–April, 1999.
Rights and permissions
About this article
Cite this article
Shpan'ko, I.V. Structure-reactivity cross correlations in nucleophilic substitution: Isoparametricity and transition-state structure. Theor Exp Chem 35, 63–74 (1999). https://doi.org/10.1007/BF02511491
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02511491