Reactions of aryl chlorothionoformates with quinuclidines. A kinetic study

Journal of Physical Organic Chemistry

Volumn 21, Issue 2, 2008, Pages 102-107

  Castro, Enrique A ^a,c   Aliaga, Margarita ^a   Campodonico, Paola R ^a   Leis, J Ramón ^b   García Río, Luis ^b   Santos, José G ^a,c  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

^b UNIVERSIDAD DEL DESARROLLO   (Chile)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Aminolysis; Aryl chlorothionoformates; Bronsted plots; Kinetics; Mechanism

Indexed keywords

HYDROLYSIS; IONIC STRENGTH; NITROGEN COMPOUNDS; SUBSTRATES;

CHLOROTHIONOFORMATES; PSEUDOFIRST-ORDER RATE COEFFICIENTS; ZWITTERIONIC TETRAHEDRAL INTERMEDIATE;

REACTION KINETICS;

EID: 39349115653     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1286     Document Type: Article

References (22)

1. E. A. Castro, Chem. Rev. 1999, 99, 3505-3524 and references therein.
2. D. N. Kevill, M. J. D'Souza, Can. J. Chem. 1999, 77, 1118-1122.
3. H. K. Oh, J. S. Ha, D. D. Sung, I. Lee, J. Org. Chem. 2004, 69, 8219-8223.
4. a) E. A. Castro, M. Cubillos, J. G. Santos, J. Org. Chem. 1997, 62, 4395-4397;
5. b) E. A. Castro, M. Cubillos, J. G. Santos, J. Org. Chem. 2004, 69, 4802-4807.
6. H. R. Al-Kazimi, D. S. Tarbell, D. Plant, J. Am. Chem. Soc 1955, 77, 2479-2482.
7. R. P. Bell, The Proton in Chemistry. Methuen, London, 1959. p. 159.
8. E. A. Castro, M. Aliaga, P. R. Campodónico, J. R. Leis, L. García-Río, J. G. Santos, J. Phys. Org. Chem. 2006, 19, 683-688.
9. [81 M. J. Gresser, W. P. Jencks, J. Am. Chem. Soc. 1977, 99, 6963-6970.
10. E. A. Castro, M. G. Ruiz, J. G. Santos, Int. J. Chem. Kinet. 2001, 33, 281-287.
11. A. Albert, E. P. Serjeant, The Determination of Ionization Constants. Chapman and Hall Ltd, London, 1971. p. 87.
12. E. A. Castro, M. G. Ruiz, S. Salinas, J. G. Santos, J. Org. Chem. 1999, 64, 4817-4820.
13. a) R. G. Pearson, J. Chem. Educ. 1968, 45, 581-587;
14. b) R. G. Pearson, J. Org. Chem. 1989, 54, 1423-1430;
15. c) Eds.: K. D. Sen, D. M. P. Mingos, Chemical Hardness, Structure and Bonding. Springer-Verlag, Berlin, 1993;
16. d) R. G. Pearson, Coord. Chem. Rev. 1990, 700, 403-425;
17. e) Ed.: R. G. Pearson, Hard and Soft Acids and Bases. Dowden, Hutchinson and Ross, Stroudsburg, PA, 1973.
18. a) R. G. Pearson, J. Chem. Educ. 1987, 64, 561-567;
19. b) R. G. Parr, P. K. Chattaraj, J. Am. Chem. Soc 1991, 237, 1854-1855;
20. c) P. K. Chattaraj, G. H. Liu, R. G. Parr, Chem. Phys. Lett. 1995, 237, 171-176.
21. M. J. Frisch, GAUSSIAN 98. Pittsburg, PA, 1998.
22. R. G. Parr, L. V. Szentpály, S. Liu, J. Am. Chem. Soc 1999, 121, 1922-1924.