Rate-limiting step and micellar catalysis of the non-classical nitro group nucleophilic substitution by thiols in 4-nitro-N-n-butyl-1,8-naphthalimide

Journal of Physical Organic Chemistry

Volumn 16, Issue 6, 2003, Pages 311-317

  Triboni, E R ^a   Politi, M J ^a   Cuccovia, I M ^a   Chaimovich, H ^a   Berci Filho, P ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Kinetics; Micellar catalysis; Nitronaphthalimides; Nucleophilic substitution; Thiol substitution

Indexed keywords

CATALYSIS; COLUMN CHROMATOGRAPHY; CRITICAL MICELLE CONCENTRATION; FLUORESCENCE; GAS CHROMATOGRAPHY; MICELLES; NITROGEN COMPOUNDS; REACTION KINETICS; SPECTROPHOTOMETERS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

RATE-LIMITING STEPS;

AROMATIC COMPOUNDS;

EID: 0037937612     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.618     Document Type: Article

References (33)

1. Laubenheimer A. Chem. Ber. 1876; 9: 768-774.
2. Laubenheimer A. Chem. Ber. 1876; 9: 1826-1829.
3. Gorvin JH. Chem. Ind. (London) 1967; 36: 1525-1526.
4. Beck JR. Tetrahedron, 1978; 34: 2057-2068.
5. (a) Rusanov AL, Takekoshi T. Russ. Chem Rev. 1991; 60: 738-750;
6. (b) Takekoshi T. Polym. J. 1987; 19: 191-202;
7. (c) Takekoshi T, Kochanowski JE, Manello JS, Webber MJ. J. Polym. Sci. A Polym. Chem. 1985; 23: 1759-1769;
8. (d) White DM, Takekoshi T, Williams FJ, Relles HM, Donahue PE, Klopfer HJ, Loucks GR, Manello JS, Matthews RO, Schluenz RW. J. Polym. Sci. A Polym. Chem. 1981; 19: 1635-1658.
9. Williams FJ, Donahue PE. J. Org. Chem. 1977; 42: 3414-3419.
10. Bartoli G, Todesco PE. Acc. Chem. Res. 1977; 10: 125-132.
11. Miller J, Moran JS. J. Chem. Res. (S), 1980; 62.
12. (a) Alexiou MS, Tyman JHP. J. Chem. Res. (S) 2000; 208-210;
13. (b) Alexiou M, Tyman JHP. J. Chem. Res. (M) 2000; 0632-0652.
14. Alexiou M, Tyman, J. Tetrahedron Lett. 1981; 22: 2303-2306.
15. Montanari S, Paradisi C, Scorrano G. J Org. Chem. 1991; 56: 4274-4279.
16. Middleton RW, Parrick J. J. Heterocycl. Chem. 1985; 22: 1567-1572.
17. (a) Middleton RW, Parrick J. Clarke ED. J. Heterocycl. Chem. 1986; 23: 849-855;
18. (b) Alexiou MS, Tychopoulos V, Ghorbanian S, Tyman JHP, Brown RG, Brittain PI. J. Chem. Soc., Perkin Trans. 2 1990; 837-842.
19. Hodgkiss RJ, Middleton RW, Stratford MRL, DelBuono R. Biochem. Pharmacol. 1987; 36: 1483-1487.
20. (a) Dubey KK, Singh RK, Misra, K. Indian J. Chem. 1995; 34B: 876-878;
21. (b) Grayshan PH, Mak KHR, Peters ST. J. Appl. Chem. Biotechnol. 1974; 24: 121-130;
22. (c) Ghorbanian, S, Tyman JHP, Tychopoulos V. J. Chem. Technol. Biotechnol. 2000; 75: 1127-1134.
23. Ellman GL. Arch. Biochem. Biophys. 1959; 82: 70-77.
24. Schales O, Schales SS. J. Biol. Chem. 1941; 140: 879-884.
25. Fendler JH. Catalysis in Micellar and Macromolecular Systems. Academic Press: New York, 1975.
26. Barros TC, Molinari OR, Berci Filho P, Toscano VG, Politi MJ. J. Photochem. Photobiol. 1993; 76: 55-60.
27. Yabroff DL. Ind. Eng. Chem. 1940; 32: 257-262.
28. Correia WR, Cuccovia IM, Chaimovich H. J. Phys. Org. Chem. 1993; 6: 7-14.
29. Weast RC (ed). CRC Handbook of Chemistry and Physics (52nd edn). Chemical Rubber Co.: Cleveland, OH, 1971-72.
30. Quina FH, Chaimovich H. J. Phys. Chem. 1979; 83: 1844-1850.
31. Chaimovich H, Bonilha JBS, Zanette D, Cuccovia IM. In Surfactants in Solution, vol. 2, Mittal KL, Lindman B (eds). Plenum Press, New York, 1984; 1121-1138.
32. (a) Chaimovich H, Bonilha JBS, Politi MJ, Quina FH. J. Phys. Chem. 1979; 83: 1851-1854;
33. (b) Bonilha JBS, Chiericato G Jr, Martins-Franchetti SM, Ribaldo EJ, Quina FH. J. Phys. Chem. 1982; 86: 4941-4947.