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http://dx.doi.org/10.5012/bkcs.2005.26.7.1037

Unexpected Rate Retardation in the Formation of Phthalic Anhydride from N-Methylphthalamic Acid in Acidic H2O-CH3CN Medium  

Ariffin, Azhar (Department of Chemistry, Faculty of Science, University Malaya)
Khan, M. Niyaz (Department of Chemistry, Faculty of Science, University Malaya)
Publication Information
Bulletin of the Korean Chemical Society / v.26, no.7, 2005 , pp. 1037-1043 More about this Journal
Abstract
Kinetic study on the cleavage of N-methylphthalamic acid (NMPA) in mixed acidic aqueous-acetonitrile solvent reveals the formation of both phthalic anhydride (PAn) (through O-cyclization) and N-methylphthalimide (NMPT) (through N-cyclization). The formation of NMPT varies from $\sim$20% to $\sim$3% with the increase in the content of acetonitrile from 2 to 70% v/v. Pseudo first-order rate constants for the formation of PAn are more than 4-fold larger than those for the formation of NMPT at 2% v/v $CH_3CN$ in mixed aqueous solvents. Pseudo first-order rate constants for alkaline hydrolysis of NMPT reveal a nonlinear decrease with increase in the content of $CH_3CN$ in mixed aqueous solvents.
Keywords
Phthalic anhydride; Kinetics; Hydrolysis; O-Cyclization and N-cyclization of N-methylphthalamic acid;
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1 Bender, M. L. J. Am. Chem. Soc. 1957, 79, 1258   DOI
2 Bender, M. L.; Chow, Y.-L.; Choluopek, F. J. Am. Chem. Soc. 1958, 80, 5380   DOI
3 ldersley, M. F.; Kirby, A. J.; Lancaster, P. W.; McDonald, R. S.; Smith, C. R. J. Chem. Soc. Perkin Trans. 2 1974, 1487
4 Leng, S. Y.; Ariffin, A.; Khan, M. N. Int. J. Chem. Kinet. 2004, 36, 316   DOI   ScienceOn
5 Khan, M. N. Indian J. Chem. 1993, 32A, 387
6 Khan, M. N. Int. J. Chem. Kinet. 1991, 23, 567   DOI
7 Zerner, B.; Bender, M. L. J. Am. Chem. Soc. 1961, 83, 2267   DOI
8 Menger, F. M.; Ladika, M. J. Am. Chem. Soc. 1988, 110, 6794   DOI
9 Khan, M. N.; Ariffin, A. Org. Biomol. Chem. 2003, 1, 1404   DOI   ScienceOn
10 Kluger, R.; Chin, J.; Choy, W.-W. J. Am. Chem. Soc. 1979, 101, 6976   DOI   ScienceOn
11 Hawkins, M. D. J. Chem. Soc. Perkin Trans. 2 1976, 642
12 Blackburn, R. A. M.; Capon, B.; McRitcie, A. C. Bioorg. Chem. 1977, 6, 71   DOI
13 Kluger, R.; Lam, C. H. J. Am. Chem. Soc. 1975, 97, 5536-5540   DOI
14 Kluger, R.; Lam, C. H. J. Am. Chem. Soc. 1978, 100, 2191   DOI
15 Khan, M. N. Indian J. Chem. 1993, 32A, 395
16 Khan, M. N. J. Org. Chem. 1996, 61, 8063   DOI   ScienceOn
17 Khan, M. N. J. Phys. Org. Chem. 1998, 11, 216   DOI   ScienceOn
18 Brown, J.; Su, S. C. K.; Shafer, J. A. J. Am. Chem. Soc. 1966, 88, 4468   DOI
19 Khan, M. N. J. Chem. Soc. Perkin Trans. 2 1988, 213
20 Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345   DOI
21 Granados, A. M.; de Rossi, R. H. J. Org. Chem. 2001, 66, 1548   DOI   ScienceOn
22 Hine, J. Structural Effects on Equilibria in Organic Chemistry; Wiley: New York, 1975; p 91
23 Angelova, V. T.; Kirby, A. J.; Koedjikov, A. H.; Pojarlieff, I. G. Org. Biomol. Chem. 2003, 1, 859   DOI   ScienceOn
24 Kirby, A. J.; Lancaster, P. W. J. Chem. Soc. Perkin Trans. 2 1972, 1206
25 Onofrio, A. B.; Gesser, J. C.; Joussef, A. C.; Nome, F. J. Chem. Soc. Perkin Trans. 2 2001, 1863
26 Perry, C. J. J. Chem. Soc. Perkin Trans. 2 1997, 977
27 Wu, Z.; Ban, F.; Boyd, R. J. J. Am. Chem. Soc. 2003, 125, 3642   DOI   ScienceOn
28 Morawetz, H.; Shafer, J. J. Am. Chem. Soc. 1962, 84, 3783   DOI