Effects of tetraalkylammonium salts on alkaline hydrolysis of N-(2-Methoxyphenyl) Phthalimide

Ariffin, A.; Khan, M.N.; Leng, S.Y. (2004) Effects of tetraalkylammonium salts on alkaline hydrolysis of N-(2-Methoxyphenyl) Phthalimide. Malaysian Journal of Science, 23 (2). pp. 175-180.

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Abstract

The effects of the concentrations of Me₄NCI, Pr₄NCl, Bu₄NCl, Me₄NBr, Pr₄NBr and Bu₄NBr on the rate of alkaline hydrolysis of N-(2-methoxyphenyl)phthalimide (N-2MPhPT) at 35°C and in H₂0 solvent containing 2 % (v/v) CH₃CN reveal the formation of ion-pair complexes between solvent - separated loose ion-pair forms ($M^n^+$ ⋯ $X^k^-$) and N-2MPhPT. The bulky hydrophobic tails of tetraalkylammonium salts and their halide anions inhibit the reaction by blocking the OH�?� nucleophilic attack on the reactive site of N-2MPhPT. Among all the quaternary ammonium salts, Me₄NCI showed slight inhibition only because of the shielding effect created by the methyl group is very small. However, Bu₄NBr presents the greatest inhibition on hydrolysis rate because of its strong binding affmity with N-2MPhPT.

Item Type: Article
Creators:
  1. Ariffin, A.(Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA)
  2. Khan, M.N.
  3. Leng, S.Y.
Journal or Publication Title: Malaysian Journal of Science
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: Tetraalkylammonium Salts, Alkaline Hydrolysis, N-(2-Methoxyphenyl)Phthalimide, Hydrophobic Interactions
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 17:02
Last Modified: 03 Jul 2013 17:02
URI: http://eprints.um.edu.my/id/eprint/8043

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