Micellar charge effects as mechanistic criteria in spontaneous hydrolyses of acid chlorides

Journal of Physical Organic Chemistry

Volumn 18, Issue 2, 2005, Pages 115-120

  Bunton, Clifford A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Acyl chlorides; Micellar rate effects; Nucleophilic substitution; Reaction mechanism; Spontaneous hydrolysis; Sulfonyl chlorides

Indexed keywords

CHLORINE COMPOUNDS; DISSOCIATION; HYDROLYSIS; POSITIVE IONS; REACTION KINETICS; SOLVENTS; SUBSTITUTION REACTIONS;

ACYL CHLORIDES; MICELLAR RATE EFFECTS; NUCLEPHILIC SUBSTITUTION; SPONTANEOUS HYDROLYSIS; SULFONYL CHLORIDES;

MICELLES;

EID: 12444316057     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.747     Document Type: Conference Paper

References (46)

1. Tascioglu S. Tetrahedron 1996; 52: 1113-11152.
2. Romsted LS, Bunton CA, Yao J. Curr. Opin. Colloid Interface Sci. 1997; 2: 622-626.
3. Sepulveda L, Lissi E, Quina F. Adv. Colloid Interface Sci. 1986; 35: 1-57.
4. (a) Romsted LS. In Surfactants in Solution, Mittal KL, Lindman B (eds). Plenum Press: New York, 1984; 1015-1068;
5. (b) Bunton CA, Nome F, Romsted LS, Quina F, Acc. Chem. Res. 1991; 24:357-363.
6. (a) Rodenas E, Ortega F. J. Phys. Chem. 1987; 91: 837-840;
7. (b) Bunton CA, Moffatt JR. J. Phys. Chem. 1986; 90: 538-541.
8. Chaudhuri A, Romsted LS. J. Am. Chem. Soc. 1991; 113: 5052-5053.
9. Savelli G, Gemani R, Brinchi L. In Reactions and Synthesis in Surfactant Systems, Texter J (ed). Marcel Dekker: New York, 2001; 175-246.
10. Menger FM, Portnoy CE. J. Am. Chem.Soc. 1967; 89:4698-4703.
11. Germani R, Ponti PP, Romeo T, Savelli G, Spreti N, Cerichelli G, Luchetti L, Mancini G, Bunton CA. J. Phys. Org. Chem. 1989; 2: 553-558.
12. Del Rosso F, Bartoletti A, DiProfio P, Savelli G, Blasko A, Bunton CA. J. Chem. Soc., Perkin Trans. 2 1995; 673-678.
13. (a) Zachariasse KA, Phuc NY, Kosankiewicz C. J. Phys. Chem. 1981; 85:2676-2683;
14. (b) Ramachandran C, Pyter RA, Mukerjee P. J. Phys. Chem. 1982; 86: 3198-3205;
15. (c) Novaki LP, El Seoud OA. Phys. Chem. Chem. Phys. 1991; 1: 1957-1964;
16. (d) Novaki LP, El Seoud OA. Langmuir 2000; 16: 35-41.
17. (a) Ingold CK. Structure and Mechanism in Organic Chemistry (2nd edn). Cornell University Press: Ithaca, NY, 1969; Chapt. 7;
18. (b) Lowry TH, Richardson KS. Mechanism and Theory in Organic Chemistry (3rd edn). Harper and Row: New York, 1987; Chapt. 4.
19. (a) Bunton CA, Perry SG. J. Chem. Soc. 1960; 3070-3079;
20. (b) Song SB, Jencks WP. J. Am. Chem. Soc. 1989; 111: 8470-8479.
21. (a) Kevill DN. In The Chemistry of Acyl Halides, Patai S (ed). Wiley: Chichester, 1972; Chapt. 12;
22. (b) Kevill DN, D'Souza MJ. J. Chem. Soc., Perkin Trans. 2 1997; 1721-1724;
23. (c) Kevill DN, Wang WFK. J. Chem. Soc., Perkin Trans. 2 1998; 2631-2638;
24. (d) Kevill DN, D'Souza MJ. J. Phys. Org. Chem. 2002; 15: 881-888, and references cited therein.
25. Cramer CJ. Essentials of Computational Chemistry. Wiley: New York, 2002; Chapt. 9.
26. Bunton CA, Gillitt ND, Mhala MM, Moffatt JR, Yatsimirsky AK. Langmuir 2000; 16: 8595-8603.
27. Bunton CA, Mhala MM, Moffatt JR. J. Org. Chem. 1985; 50: 4921-4924.
28. (a) Buurma NJ, Herranz AM, Engberts JBFN. J. Chem. Soc. Perkin Trans. 2 1999; 113-119;
29. (b) Possidonio S, Siviero F, El Seoud OA. J. Phys. Org. Chem. 1999; 12: 325-332;
30. (c) Possidonio S, El Seoud OA. J Mol. Liq. 1999; 80: 231-251.
31. (a) Al-Lohedan H, Bunton CA, Mhala MM. J. Am. Chem. Soc. 1982; 104: 6654-6660;
32. (b) Bunton CA. In Nucleophilicity, Harris JM, McManus SP (eds). Advances in Chemistry Series 215. American Chemical Society: Washington, DC, 1987; Chapt. 29;
33. (c) Bunton CA, Ljunggren S. J. Chem. Soc., Perkin Trans. 2 1984; 355-361;
34. (d) Bunton CA, Gillitt ND, Mhala MM, Moffatt JR. Croat. Chem. Acta 2001; 74: 559-573;
35. (e) Brinchi L, Di Profio P, Micheli F, Germani R, Savelli G, Bunton CA. Eur. J. Org. Chem. 2001; 1115-1120.
36. (a) Bunton CA, Mhala MM, Moffatt JR. J. Phys. Chem. 1989; 93: 854-858;
37. (b) Di Profio P, Germani R, Savelli G, Cerichelli G, Chiarini M, Mancini G, Bunton CA, Gillitt ND. Langmuir 1998; 14: 2662-2669.
38. Baptista daSilva M, Cuccovia I, Chaimovich H, Politi MJ, Reed WF. J. Phys. Chem. 1992; 96: 6442-6449.
39. Johnson SL. Adv. Phys. Org. Chem. 1967; 5: 237-330.
40. (a) Hudson RF, Moss G. J. Chem. Soc. 1969; 3599-3604;
41. (b) Hudson RF, Moss G. J. Chem. Soc. 1964; 1040-1045.
42. Fernandez MS, Fromherz P. J. Phys. Chem. 1977; 81: 1755-1761.
43. (a) Almgren M, Rydholm R. J. Phys. Chem. 1979; 83: 360-364;
44. (b) Drummond CJ, Grieser F, Healy TW. J. Chem. Soc., Faraday Trans. 1 1989:85:551-560.
45. (a) Kice JL. Adv. Phys. Org. Chem. 1980; 17: 65-181;
46. (b) Kevill DN, D'Souza MJ. Collect. Czech. Chem.Commun. 1999; 64: 1790-1796.