Theoretical Study on Acid catalyzed hydrolysis of Esters.

DOI
  • Hori Kenzi
    Graduate School of Science and Engineering, Yamaguchi Univ.
  • Ikenaga Yutaka
    Graduate School of Science and Engineering, Yamaguchi Univ.

Bibliographic Information

Other Title
  • エステルの酸加水分解に関する理論的研究

Description

Hydrolysis mechanism of methylacetate in the acidic conditions was investigated at the MP2/6-311+G(d,p)// MP2/6-31+G(d,p) level of theory. It is necessary to include two waters as reactants to obtain a tetrahedral (TD) intermediate for the AAC2 mechanism that Ingold classified for hydrolysis of methylacetate. The mechanism includes two TS structures, one for formation of the TD intermediate and the other for its decomposition. As activation energies were calculated to be 15.7 and 18.3 kcal mol-1, the second step determines the rate of hydrolysis. The calculated value is close to that observed, ~16 kcal mol-1. It was confirmed that the AAC2 mechanism has a barrier lower by 9.9 kcal mol-1 than that for the AAL2 mechanism. The AAC2 mechanism is also applicable to the acid catalyzed hydrolysis of acetamide

Journal

Keywords

Details 詳細情報について

  • CRID
    1390001205555372672
  • NII Article ID
    130004645171
  • DOI
    10.11494/kisoyuki.18.0.71.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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