Solvolysis of substituted benzoyl chlorides in nonionic and mixed micellar solutions.

P Campos-Rey, Celia Cabaleiro-Lago, P Hervés

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The solvolysis of substituted benzoyl chlorides is sensitive both to substituent electronic effects and to medium effects. The solvolysis reactions of substituted benzoyl chlorides have been analyzed in the presence of nonionic micelles. The reaction is inhibited or catalyzed depending on the reaction mechanism, dissociative or associative, respectively. The micellar effects observed can be related to the low water content and low polarity of the interface as well as an increase of the nucleophilic character of the interfacial water. Moreover, the effect of the micellar surface charge on the solvolysis mechanism with high associative character was systematically studied. Mixed micelles of nonionic-ionic surfactants with a variable ionic content were prepared and characterized regarding charge and polarity. A correlation between the net charge of the micelles and the rate constants at the micellar interface was observed. The results suggest that the transient state for this mechanism is highly stabilized in a positively charged environment while the negative surface given by anionic micelles strongly inhibit the solvolysis reaction.

Original languageEnglish
Pages (from-to)14004-14011
Number of pages7
JournalJournal of Physical Chemistry B
Volume114
Issue number44
DOIs
Publication statusPublished - 2010
Externally publishedYes

Swedish Standard Keywords

  • Physical Chemistry (10402)

Keywords

  • Anionic micelles
  • Chlorine compounds
  • Mixed micelles
  • Nonionic surfactants
  • Organic compounds
  • Rate constants
  • Reaction mechanism
  • Solvents
  • Transient state
  • Water content

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