The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis

Febdian Rusydi, Nufida D. Aisyah, Rizka N. Fadilla, Hermawan K. Dipojono, Faozan Ahmad, Mudasir, Ira Puspitasari, Andrivo Rusydi

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

We report a first-principles study on ethyl acetate neutral hydrolysis in which we focus on the activation energy variation resulting from the conformational effect in the transition state. We use the conformers of ethyl formate, ethyl acetate, ethyl fluoroacetate, and ethyl chloroacetate as the ester models and one water molecule with a one-step reaction mechanism. We also consider the long-range interaction and the surrounding water in the form of PCM. Our results show that the various conformers yield a significant range of activation energy. Moreover, the gauche conformer has lower activation energy than the trans conformer. The activation energy in its own right is lowered by the halogen atoms. Finally, we remark that the long-range correction and PCM stabilize the transition state geometry but raise the activation energy.

Original languageEnglish
Article numbere02409
JournalHeliyon
Volume5
Issue number9
DOIs
Publication statusPublished - Sept 2019

Keywords

  • Activation energy
  • Conformational effect
  • Density functional theory
  • Ester
  • Ethyl acetate
  • First-principles calculations
  • Long-range correction
  • Neutral hydrolysis
  • Organic chemistry
  • Physical chemistry
  • Theoretical chemistry

Fingerprint

Dive into the research topics of 'The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis'. Together they form a unique fingerprint.

Cite this