𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Theoretical analysis on alkaline hydrolysis mechanisms of N-(2-methoxyphenyl) benzamide

✍ Scribed by Yifan Jin; Yanyan Zhu; Mingsheng Tang

Publisher
Elsevier
Year
2011
Tongue
English
Weight
713 KB
Volume
963
Category
Article
ISSN
2210-271X

No coin nor oath required. For personal study only.

✦ Synopsis

Reaction mechanisms of alkaline hydrolysis of N-(2-methoxyphenyl) benzamide have been investigated using density functional theory (DFT). The whole reaction could be regarded as a successive process that consisted of two main stages: generation of the tetrahedral intermediate (M1) and the transformation from M1 to the final products. Three reaction channels were proposed for the second stage. Channel 1 is an intramolecular proton migration process. In channel 2 and channel 3, which could be regarded as an intermolecular proton migration process, the water molecule participates in the reaction and becomes a medium of proton transferring. We found that the rate-determining activation energy required for channel 2 and 3 is lower than channel 1, which indicates that the water not only acts as the solvent, but also plays an important role in the reaction. And this reaction could occur easily at room temperature, which is in good agreement with the experiments.

📜 SIMILAR VOLUMES

Theoretical studies on the alkaline hydr
Theoretical studies on the alkaline hydrolysis of N-Methylcarbamates
✍ Toshiyuki Katagi 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 English ⚖ 542 KB

The reaction mechanisms of the alkaline hydrolysis of N-methylcarbamates were studied using the AM1 method by assuming two possible pathways: (1) nucleophilic attack of hydroxide ion on the car-bony1 carbon to give a tetrahedral complex followed by its breakdown to carbamic acid (BA,~); and (2) prot

Kinetics and mechanism of hydrolysis of
Kinetics and mechanism of hydrolysis of N-(2′-hydroxyphenyl)phthalamic acid (1) and N-(2′-methoxyphenyl)phthalamic Acid (2) in a highly alkaline medium
✍ Yoke-Leng Sim; Emmy Fadhiza Damit; Azhar Ariffin; M. Niyaz Khan 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 160 KB

## Abstract A kinetic study on hydrolysis of N‐(2′‐hydroxyphenyl)phthalamic acid (**1**), N‐(2′‐methoxyphenyl)phthalamic acid (**2**), and N‐(2′‐methoxyphenyl)benzamide (**3**) under a highly alkaline medium gives second‐order rate constants, __k__~OH~, for the reactions of HO^−^ with **1, 2**, and

Theoretical study on the hydrolysis mech
Theoretical study on the hydrolysis mechanism of N,N-dimethyl-N′-(2-oxo-1, 2-dihydro-pyrimidinyl)formamidine: Water-assisted mechanism and cluster-continuum model
✍ Yong Wu; Lu Jin; Ying Xue; Dai Qian Xie; Chan Kyung Kim; Yong Guo; Guo Sen Yan 📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 English ⚖ 532 KB

## Abstract The hydrolysis reaction of __N__,__N__‐dimethyl‐N′‐(2‐oxo‐1, 2‐dihydro‐pyrimidinyl)formamidine (DMPFA), a model compound of the antivirus drug amidine‐3TC (3TC = 2′, 3′‐dideoxy‐3′‐thiacytidine), is investigated by the hybrid density functional theory B3LYP/6‐31+G (d,p) method. The hydro