EFFECTS OF TETRAALKYLAMMONIUM SALTS ON ALKALINE HYDROLYSIS OF N-(2-METHOXYPHENYL) PHTHALIMIDE

Authors

  • Sim Yoke Leng Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.
  • M. Niyaz Khan Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.
  • Azhar Ariffin Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.

Keywords:

Tetraalkylammonium Salts, Alkaline Hydrolysis, N-(2-Methoxyphenyl)Phthalimide, Hydrophobic Interactions

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⻠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.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⻠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.

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Published

26-08-2004

How to Cite

Yoke Leng, S., Khan, M. N., & Ariffin, A. (2004). EFFECTS OF TETRAALKYLAMMONIUM SALTS ON ALKALINE HYDROLYSIS OF N-(2-METHOXYPHENYL) PHTHALIMIDE. Malaysian Journal of Science (MJS), 23(2), 175–180. Retrieved from https://samudera.um.edu.my/index.php/MJS/article/view/8459

Issue

Vol. 23 No. 2 (2004)

Section

Original Articles

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