Kinetic and mechanistic aspects of acid-catalysed hydrolysis of hydroxamic acids

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 36, Issue 12, 1997, Pages 1089-1102

  Ghosh, Kallol K ^a  

^a PT RAVISHANKAR SHUKLA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0642363738     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (122)

1. Lossen W, Ann Chem, 176, 1895, 281.
2. Bamberger E, Ber, 51, 1918, 636.
3. Yale H L, Chem Rev, 33, 1943, 209.
4. Shome S C, Analyst, 75, 1950, 27.
5. Yost Y & Gutmann H R, J Chem Soc C, 1969, 345.
6. Tandon S G & Bhattacharya S C, J Chem Engng Data, 7, 1962, 533, Anal Chem, 33, 1961, 1267.
7. Tandon S G & Bhattacharya S C, J Chem Engng Data, 7, 1962, 533, Anal Chem, 33, 1961, 1267.
8. Miyauchi M, Takou Y, Watanabe M & Uematsu T, Chem Biol Interact, 51, 1984, 49.
9. Matlin S A, Sammes P G & Upton R M, J Chem Soc Perkin Trans-I 1979, 2481.
10. (a) Sakamoto Y, Yoshioka T, Uematsu T, J Org Chem, 54, 1989, 4449.
11. (b) Sakamoto T & Kikugawa Y, J Org Chem, 59, 1994, 929.
12. Gupta V K & Tandon S G, J Indian Chem Soc, 46, 1969, 831.
13. Corbett M D & Corbett B R, J Org Chem, 45, 1980, 2834.
14. Sandler S R & Karo W, Hydroxamic acid in organic functional group preparations, Vol. III, (Academic Press) 1983, 482.
15. Nikam S S, Kornberg B E, Johnson D R & Doherty A M, Tetrahedron Lett, 36, 1995, 197.
16. Koshti N M, Jacobs H K, Martin P A, Smith P H & Gopalan A S, Tetrahedron Lett, 35, 1994, 5157.
17. (a) Thomas A & Rajappa S, Tetrahedron, 51, 1995, 10571.
18. (b) Chittari P, Thomas A & Rajappa S, Tetrahedron Lett, 35, 1994, 3793.
19. Lipczynska-Kochany E, Chem Rev, 91, 1991, 477.
20. Parekh P C & Agrawal Y K, J Chem Soc Perkin Trans-II, 1987, 479.
21. Monyk B & Crumbliss A L, J Org Chem, 45, 1980, 4670.
22. Brink C P & Crumbliss A L, J Org Chem, 7, 1982, 1171.
23. Brink C P, Fish L L & Crumbliss A L, J Org Chem, 50, 1985, 2277.
24. Hrzit J & Pande R, J Indian Chem Soc, 71, 1994, 161.
25. (a) Agrawal Y K & Roshania R D, Thermochim Acta, 42, 1980, 1
26. (b) Agrawal Y K & Shukla J P, Aust J Chem, 26, 1973, 913.
27. Bordwell F G, Fried H E, Hughes D L, Lynch T Y & Satish A V & Whang Y E, J Org Chem, 55, 1990, 3330.
28. Lipczynska-Kochany E & Iwamura H, J Org Chem, 47, 1982, 5277.
29. Decouon M, Exner O, Ga J F & Maria P C, J Org Chem, 55, 1990, 3980.
30. Turi L, Dannengerg J J, Rama J & Ventura O N, J Phys Chem, 96, 1992, 3709.
31. (a) Exner O, Hardil M & Mollin J, Collect Czech Chem Commun, 58, 1993, 1109.
32. (b) Agrawal Y K, Russ Chem (Engl Transl), 48, 1979, 948.
33. (a) Remko M, Mach P, Schleyer P V R & Exner O, J Mol Struct (Theochem), 279, 1993, 139.
34. (b) Chatterjee B, Coord chem Rev, 26, 1978, 281.
35. (a) Bagno A, Comuzzi C & Sccrrano G, J Am Chem Soc, 116, 1994, 916.
36. (b) Agrawal Y K & Patel S A, Rev Anal Chem, 4, 1980, 237.
37. Majumdar A K, Int Ser Monogr Anal Chem, 50, 1971.
38. Raymond K N, Muller G & Matzanke B F, Top Curr Chem, 123, 1984, 49.
39. Liu C Y, Chen M J, Lee N M, Hwang H C, Jou S T & Hsu J C, Polyhydron, 11, 1192, 551.
40. Shrivastava A K, Tandon S G, Ind Environ Health, 24, 1982, 89.
41. Nanewar R R & Tandon U, Talanta, 25, 1978, 352.
42. Abbasi S A & Hameed S A, Analyst, 113, 1988, 1561.
43. Kurzak B, Kozlowski H & Farkas E, Coord Chem Rev, 1992.
44. (a) Bergeron R J, Wiegand J, McManis J S & Perumal P T, J Med Chem, 35, 1992, 4739.
45. (b) Bergeron R J, Liu Z R, McManis J S & Weigand J, J Med Chem, 35, 1992, 4739.
46. (a) Buu-Hoi N P, Lambelin G, Lepoivre C, Gillet G, Gautier M & Thiriaux J, Com Rend, 261, 1965, 2259.
47. (b) Grady R W, Graziano J H, Akerz A H & Gerami A, J Pharmacol Exp Ther, 196, 1976, 478.
48. Powers J C & Harper J W, Review on hydroxamic acid as metalloprotease inhibitors in protease inhibitors, edited by A J Barrett and G Salvesan, 1986, 219.
49. Crumbliss A L, Garrison J M, Book C R, Schaff A & Bonaventura C J, Bonaventura, J Inorg Chem Acta, 133, 1987, 281.
50. Miller M J, Chem Rev, 89, 1989, 1563.
51. Crumbliss A L, Coord Chem Rev, 105, 1990, 155.
52. Miller M J & Malouin F, In: The development of iron chelaros for clinical use, edited by R J Bergeron and Britteham (CRC Press, Boca Raton) 1994, 275.
53. Raymond K N, Coord Chem Rev, 105, 1990, 1353.
54. Neiland J B & Valenta J R, Metal ions in biological systems, edited by H Sigel (Marcel Dekker, NY) 1985.
55. Nagasaki T & Shinkai S J, Chem Soc Perkin Trans-II, 1991, 689.
56. Waid L S, Hydroxamic acids in soil systems; Soil Biochemistry, edited by E A Paul and A D McLaren (Marcel Dekker, NY) 1975, 65.
57. Hase J, Kobashi K, Kawaguchi N & Sakamoto K, Chem Pharm Bull, 19, 1971, 363.
58. Lipczynska-Kochany E, Iwamura H, Takahashi K, Hakura A & Kawazoe Y, Mutat Res, 135, 1984, 139 and references cited therein.
59. (a) Ritter C L & Malejka Giganti D, Biochem Biophys Res Commun, 131, 1985, 174.
60. (b) Malejka-Giganti D, Ritter C L, Dekker R W & Suliman J M, Cancer Res, 46, 1986, 6200.
61. Malejka-Giganti D & Ritter C L, In: Carcinogenic and mutagenic responses to aromatic amines and nitroarenes, edited by C M King, L J Romano and D Schuetle (Elsevier) 1988, 199.
62. Helmick J S, Martin K A, Heinrich J L & Nokak M, J Am Chem Soc, 113, 1991, 3459.
63. (a) Hashimoto S & Nakumura Y, J Chem Soc Chem Commun, 1995, 1413.
64. (b) Hashimoto S, Yamashita R & Nakamura Y, Chem Lett, 1992, 1639.
65. (a) Joshi R R & Ganesh K N, Proc Indian Acad Sci (Chem Sci), 106, 1994, 1089.
66. (b) Joshi R R & Ganesh K N, Biochem Biophys Res Commun, 1982, 1992, 588.
67. Schut H A J & Castonguay A, Drug Metab Rev, 15, 1984, 753.
68. Miller M J & Malouin F, Ace Chem Res, 26, 1993, 26.
69. (a) Kehl H, Chemistry & biology of hydroxamic acids, (Karger, New York) 1982.
70. (b) Bauer L & Exner O, Angew Chem Int Ed Engl, 13, 1974, 376.
71. Golenser J, Tsafack A, Amichai Y, Libman J, Shanzer A, Cobant C & Ioav Z, Antimicrob Agents Chemother, 39, 1995, 61.
72. Mane B S & Jagdale M H, React Kinet Catal Lett, 6, 1977, 417.
73. Berndt D C & Sharp K, J Org Chem, 38, 1973, 396.
74. Mollin J & Kucerova T, Collect Czech Chem Commun, 41, 1976, 2885.
75. Di Furia F, Modena G & Scrimin P, Nouv J de Chim, 8, 1984, 45.
76. Di Furia F, Modena G, Scrimin P, Gasparini G M & Grossi G, Sept Science and Tech, 17, 1982, 1451.
77. Mane B S & Jagdale M H, J Indian Chem Soc, 54, 1977, 615.
78. Buglass A J, Dorr M & Juffkins M, Tetrahedron Letters, 28, 1987, 3283.
79. Mane B S & Jagdale M H, Indian J Chem, 16A, 1977, 1086.
80. Berndt D C & Fuller R L, J Org Chem, 31, 1966, 3312.
81. Buglass A J, Hudson K & Tillett J G, J Chem Soc (B), 1977, 123.
82. Ahmad A, Socha J & Vecera M, Collect Czech Chem Commu, 39, 1974, 3293.
83. Ghosh K K & Tandon S G, React Kinet Catal Lett, 45, 1991, 79.
84. Ghosh K K, Rajput S K & Krishnani K K, J Phys Org Chem, 5, 1992, 39.
85. Berndt D C & Ward I E, J Org Chem, 39, 1974, 841.
86. Ghosh K K, Rajput S K & Krishnani K K, New J Chem, 17, 1993, 363.
87. Ghosh K K, Rajput S K & Krishnani K K, Indian J Chem, 32A, 1993, 139.
88. Berndt D C, J Org Chem, 39, 1974, 840.
89. Ghosh K K, Ghosh S & Thakur S S, Indian J Chem, 35B 1996, 121.
90. Novak M, Bonham G A, Mohler L K & Peet K M, J Org Chem, 53, 1988, 3903.
91. Rao C S & Tandon S G, Indian J Chem, 14A, 1976, 766.
92. Berndt D C & Ward I E, J Org Chem, 43, 1978, 13.
93. Berndt D C & Ward I E, J Org Chem, 41, 1976, 3297.
94. Ghosh K K & Tandon S G, Indian J Chem, 23A, 1984, 1004.
95. Ghosh K K & Ghosh S, Indian J Chem, 33B, 1994, 1369.
96. Ghosh K K & Krishnani K K, J Chem Res, 1993, (S), 469 (M), 3143.
97. Ghosh K K & Tandon S G, Bull Chem Soc Jpn, 62, 1989, 1304.
98. Ghosh K K, Rajput S K & Sar S K, J Indian Chem Soc, (in Press).
99. Ghosh K K, Rajput S K & Sar S K, J Indian Chem Soc, (in Press).
100. Taft R W (Jr), Steric effects in organic chemistry, edited by M S Newman (Wiley, New York), 1956, Chapter 13.
101. Shorter J, in Advances in linear free energy relationships, edited by J Shorter and N B Champman (Plenum Press, New York) 1972, Chap 2.
102. Lametais P & Carpentier J M, J Chem Res, 1981, (S), 282 (M), (3369).
103. (a) Yates K, Acc Chem Res, 4, 1971, 136.
104. (b) Yates K & McClelland R A, J Am Chem Soc, 89, 1967, 2686.
105. Edward J T & Wong S C, J Am Chem Soc, 99, 1977, 7224.
106. (a) Bunnett J F & Olsen F P, Can J Chem, 44, 1966, 1917.
107. (b) Edward J T, Derdall G D & Wong S C, J Am Chem Soc, 102, 1978, 1023.
108. (a) Cox R A, Ace Chem Re, 20, 1987, 27.
109. (b) Cox R A & Yates K, J Am Chem Soc, 100, 1978 3861.
110. Berndt D C, J Org Chem, 39, 1974, 840.
111. Ghosh K K & Krishnani K K, React Kinet Catal Lett, 49, 1993, 403.
112. McCoy L L & Riecke E E, J Am Chem Soc, 95, 1973, 7407.
113. Cox R A & Yates K, Can J Chem, 57, 1979, 2944.
114. Bagno A, Scorrano G & More O'Ferrall R A, Rev Chem Intermed, 7, 1987, 313.
115. Lobo A M, Prabhakar S & Fonseca M T C & Rodriguez A M B, Tetrahedron Lett, 36, 1977, 3167.
116. (a) Liler M, J Chem Soc Perkin Trans-II, 1979, 71.
117. (b) Liler M & Markovic D, J Chem Soc Perkin Trans-II, 1982, 551.
118. Liler M & Thwaites M M, J Chem Soc Perkin Trans-II, 1983, 201.
119. (a) Pande R & Tandon S G, Talanta, 38, 1991, 1015.
120. (b) Paul M & Pande R, Fresenius J Anal Chem, 1992, 193.
121. Decouon M, Exner O, Gal J F & Maria P C, J Org Chem, 57, 1992, 1621.
122. Ghosh K K & Ghosh S, J Indian Chem Soc. 73, 1996, 79.