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A Kinetics and Mechanism Investigation of the Nucleophilic Substitution Reaction of α‐ Chlorododecyl Carboxylate with Trimethylamine
Author(s) -
Wang Zeyun,
Zhang Shufen,
Fang Yun,
Yang HuiYan,
Qi Liyun
Publication year - 2010
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-009-1172-0
Subject(s) - chemistry , formamide , nucleophilic substitution , carboxylate , substitution reaction , reaction mechanism , nucleophile , trimethylamine , reactivity (psychology) , kinetics , solvent effects , chemical kinetics , solvation , medicinal chemistry , organic chemistry , solvent , computational chemistry , catalysis , medicine , physics , alternative medicine , pathology , quantum mechanics
A nucleophilic substitution reaction was developed to synthesize the zwitterionic surfactant using a renewable natural fatty acid rather than a petroleum derivative as the raw material. The kinetics and mechanism of the nucleophilic substitution reaction of trimethylamine α ‐chlorododecyl carboxylate with trimethylamine were investigated in protic and dipolar aprotic solvents including water, ethanol and N , N ‐dimethyl formamide. The rate equations were derived using initial rates and the activation parameters in different solvents were determined empirically and compared with each other to obtain important information about the reaction mechanism. The overall second‐order reaction number and the negative activation entropy supported a bimolecular nucleophilic substitution (S N 2) mechanism, combined with the pseudo‐first‐order kinetics for each reactant. The experimental results also showed that the reaction reactivity diminishes with the decrease in polarity of protic solvents. The typical dipolar aprotic solvent dimethyl formamide distinctively promoted the reaction in. This fact was successfully explained by the solvation rule for S N 2 reactions.