The kinetics of the hydrolysis of benzohydroxamic acid have been investigated in hydrochloric, sulphuric and perchloric acids in 10% (v/v) dimethyl sulphoxide—water at 55 °C. Activation parameters were also determined. Rate correlation by the Cox—Yates excess acidity method shows an A-2 mechanism involving rapid pre-equilibrium protonation of the substrate followed by rate-limiting attack of water at the carbonyl carbon atom to form a tetrahedral intermediate which collapses, in a fast step, to the products.

References

1 W. Lenk and M. Riedl, Proc. 9th IUPAC Conf. Phys. Org. Chem., Abstr. No. P. 69, 203 (1988).
Google Scholar
2 H. A. J. Schut and A. Castonguay, Drug Metab. Rev. 15, 753–839 (1984).
10.3109/03602538409041079
CAS PubMed Web of Science® Google Scholar
3 F. Di Furia, G. Modena, P. Scrimin, G. M. Gasparini and G. Grossi, Sep. Sci. Technol. 17, 1451–1468 (1982), and references cited therein.
10.1080/01496398208055633
CAS Google Scholar
4 P. C. Parekh and Y. K. Agrawal, J. Chem. Soc., Perkin Trans. II, 479–482 (1987), and references cited therein.
Google Scholar
5 K. K. Ghosh and S. G. Tandon, React. Kinet. Catal. Lett. 45, 79–84 (1991).
10.1007/BF02078612
CAS Web of Science® Google Scholar
6 K. K. Ghosh and S. G. Tandon, Bull. Chem. Soc. Jpn. 62, 1304–1307 (1989).
10.1246/bcsj.62.1304
CAS Web of Science® Google Scholar
7 M. Novak, G. A. Bonham, L. K. Mohler and K. M. Peet, J. Org. Chem. 53, 3903–3908 (1988).
10.1021/jo00252a003
CAS Web of Science® Google Scholar
8 A. J. Buglass, M. Dorr and M. Juffkins, Tetrahedron Lett. 28, 3283–3284 (1987).
10.1016/S0040-4039(00)95493-5
CAS Web of Science® Google Scholar
9 K. K. Ghosh and S. G. Tandon, Indian J. Chem. 23A, 1004–1007 (1984).
CAS Google Scholar
10 F. Di Furia, G. Modena and P. Scrimin, Nouv. J. Chim. 8, 45–49 (1984).
CAS Google Scholar
11 R. A. Cox, Acc. Chem. Res. 20, 27–31 (1987).
10.1021/ar00133a004
CAS Web of Science® Google Scholar
12 A. J. Buglass, K. Hudson and J. G. Tillett, J. Chem. Soc. B 123–126 (1971).
Google Scholar
13 R. A. Cox and K. Yates, Can. J. Chem. 57, 2944–2951 (1981).
10.1139/v79-479
Web of Science® Google Scholar
14 R. A. Cox and K. Yates, Can. J. Chem. 59, 2853–2863 (1981).
10.1139/v81-414
CAS Web of Science® Google Scholar
15 R. A. Cox and K. Yates, Can. J. Chem. 62, 1613–1617 (1984).
10.1139/v84-277
CAS Web of Science® Google Scholar
16 P. Lemetais and J. M. Carpentier, J. Chem. Res. (S) 34; 0358 (1983).
Google Scholar
17 C. A. Bunton, J. H. Crabtree, and L. Robinson, J. Am. Chem. Soc. 90, 1958–1265 (1968).
Google Scholar
18 J. F. Bunnett and F. P. Olsen, Can. J. Chem. 44, 1917–1931 (1966).
10.1139/v66-287
CAS Web of Science® Google Scholar
19 K. Yates and R. A. McClelland, J. Am. Chem. Soc. 89, 2686–2692 (1967).
10.1021/ja00987a033
CAS Web of Science® Google Scholar
20 V. Lucchini, G. Modena, G. Scorrano and U. Tonellato, J. Am. Chem. Soc. 99, 3387–3392 (1977), and references cited therein.
10.1021/ja00452a033
CAS Web of Science® Google Scholar
21 N. C. Marziano, P. G. Traverso, A. Tomasin and R. C. Passerini, J. Chem. Soc., Perkin Trans. 2 309–313 (1977).
Google Scholar
22 J. T. Edward, G. D. Derdall and S. C. Wong, J. Am. Chem. Soc. 102, 1023–1027 (1978).
Google Scholar
23 R. A. Cox and K. Yates, Can. J. Chem. 60, 3061–3070 (1982).
10.1139/v82-438
CAS Web of Science® Google Scholar
24 U. Priyadarshini and S. G. Tandon, J. Chem. Eng. Data 12, 143 (1967).
10.1021/je60032a046
CAS Web of Science® Google Scholar

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Volume5, Issue1

January 1992

Pages 39-43

Kinetic model for acid-catalysed hydrolysis of benzohydroxamic acid^†

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Kinetic model for acid-catalysed hydrolysis of benzohydroxamic acid†

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Kinetic model for acid-catalysed hydrolysis of benzohydroxamic acid^†