Kinetics and mechanism of the reactions of S-4-nitrophenyl 4-methylthiobenzoate with secondary alicyclic amines and pyridines

Journal of Physical Organic Chemistry

Volumn 19, Issue 8-9, 2006, Pages 555-561

  Castro, Enrique A ^a   Aguayo, Raul ^a   Bessolo, Jorge ^a   Santos, José G ^a  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

Aminolysis; Br nsted plot; Kinetics and mechanism; Pyridinolysis; Tetrahedral intermediate; Thiobenzoate

Indexed keywords

BINARY MIXTURES; ETHANOL; IONIC STRENGTH; REACTION KINETICS; WATER;

AMINOLYSIS; PYRIDINES; PYRIDINOLYSIS; TETRAHEDRAL INTERMEDIATE; THIOBENZOATE;

AMINES;

EID: 33846535285     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1055     Document Type: Conference Paper

References (43)

1. (a) Akahori Y. Chem. Pharm. Bull. 1965; 13: 368;
2. (b) Kirsch JF, Kline A. J. Am. Chem. Soc. 1969; 91: 1841;
3. (c) Menger FM, Smith JH. J. Am. Chem. Soc. 1972; 94: 3824;
4. (d) O'Leary MH, Marlier JF. J. Am. Chem. Soc. 1979; 101: 3300;
5. (e) Sawada M, Ichihara M, Ando T, Yukawa Y. Tetrahedron Lett. 1981; 22: 4733;
6. (f) Khan MN. J. Org. Chem. 1983; 48: 2046;
7. (g) Ciuffarin E, Loi A. J. Org. Chem. 1983; 48: 1047;
8. (h) Bell KH. Aus. J. Chem. 1987; 40: 1723;
9. (i) Um IH, Kwon HJ, Kwon DS, Park JY. J. Chem. Res. (S) 1995; 301;
10. (j) Lee JP, Yoon JH, Um IH. Bull. Korean Chem. Soc. 1999; 20: 805.
11. Koh HJ, Lee HC, Lee HW, Lee I. Bull. Korean Chem. Soc. 1995; 16: 839.
12. (a) Um IH, Min JS, Lee HW. Can. J. Chem. 1999; 77: 659;
13. (b) Um IH, Min JS, Ahn JA, Han HJ. J. Org. Chem. 2000; 65: 5659.
14. (a) Um IH, Back MH, Han HJ. Bull. Korean Chem. Soc. 2003; 24: 1245;
15. (b) Um IH, Park HR, Kim EY. Bull. Korean Chem. Soc. 2003; 24: 1251;
16. (c) Um IH, Kim KH, Park HR, Fujio M, Tsuno Y. J. Org. Chem. 2004; 69: 3937.
17. (a) Castro EA, Santander CL. J. Org. Chem. 1985; 50: 3595;
18. (b) Castro EA, Valdivia JL. J. Org. Chem. 1986; 51: 1668;
19. (c) Castro EA, Steinfort GB. J. Chem. Soc. Perkin Trans. 2 1983; 453;
20. (d) Castro EA, Hormazabal A, Santos JG. Int. J. Chem. Kinet. 1998; 30: 267.
21. Castro EA. Chem. Rev. 1999; 19: 3505, and references therein.
22. (a) Urn IH, Lee S-E, Kwon HJ. J. Org. Chem. 2002; 67: 8999;
23. (b) Um IH, Seok JA, Kim HT, Bae S-K. J. Org. Chem. 2003; 68: 7742.
24. Oh HK, Ku MH, Lee HW, Lee I. J. Org. Chem. 2002; 67: 8995.
25. (a) Lee I, Shim CS, Lee HW. J. Chem. Res. (S) 1992; 90;
26. (b) Lee I, Koo HJ. New J. Chem. 1996; 20:131;
27. (c) Koo HJ, Han KL, Lee I. J. Org. Chem. 1999; 64: 4783.
28. (a) Castro EA, Bessolo J, Aguayo R, Santos JG. J. Org. Chem. 2003; 68: 8157;
29. (b) Castro EA, Vivanco M, Aguayo R, Santos JG. J. Org. Chem. 2004; 69: 5399;
30. (c) Castro EA, Aguayo R, Bessolo J, Santos JG. J. Org. Chem. 2005; 70: 3530.
31. Grosser MJ, Jencks WP. J. Am. Chem. Soc. 1977; 99: 6970.
32. Castro EA, Araneda CA, Santos JG. J. Org. Chem. 1997; 62: 126.
33. (a) Bond PM, Castro EA, Moodie RB. J. Chem. Soc. Perkin Trans. 2 1976; 68;
34. (b) Castro EA, Ureta C. J. Org. Chem. 1989; 54: 2153.
35. Bunton CA, Foroudian HF, Kumar A. J. Chem. Soc. Perkin Trans. 2 1995; 33.
36. Kanaoka Y, Tanizawa K, Sato E, Yonemitsu O, Ban Y. Chem. Pharm. Bull. 1967; 15: 593.
37. (a) Satterthwait AC, Jencks WP. J. Am. Chem. Soc. 1974; 96:7018;
38. (b) Ba-Saif S, Luthra AK, Williams A. J. Am. Chem. Soc. 1987; 109: 6362.
39. Bell RP. The Proton in Chemistry. Methuen: London, 1959; 159.
40. Castro EA, Ureta C. J. Chem. Soc. Perkin Trans. 2 1991; 63.
41. Gresser MJ, Jencks WP. J. Am. Chem. Soc. 1977; 99: 6963.
42. Song BD, Jencks WP. J. Am. Chem. Soc. 1989; 111: 8479.
43. Hammond GS. J. Am. Chem. Soc. 1955; 77: 334.