Solution-phase energy profiles for trigonal bipyramidal species postulated as intermediates for the hydrolysis of methyl ethylene phosphate

T. Uchimaru, S. Kawahara, S. Tsuzuki, Kazunari Matsumura, K. Taira

Research output: Contribution to journalArticle

4 Citations (Scopus)


We present results of solution-phase ab initio and DFT investigations on the trigonal bipyramidal (TBP) intermediates postulated for the hydrolysis of methyl ethylene phosphate (MEP). A key intermediate for the hydrolysis would not be a TBP species with the hydroxyl group axial, but would be a TBP intermediate with the hydroxyl group equatorial. Considering the reaction pathways through this intermediate, not only exclusive ring opening in the dilute alkaline hydrolysis of MEP but also significant amount of exocyclic cleavage in the strong alkali can be rationalized. This interpretation is in accord with the mechanisms proposed by Lim et al. and by Lonnberg et al.

Original languageEnglish
Pages (from-to)215-221
Number of pages7
JournalJournal of Molecular Structure: THEOCHEM
Publication statusPublished - 1999 Sep 1
Externally publishedYes



  • Ab initio and DFT calculations
  • Hydrolysis of methyl ethylene phosphate
  • Pseudorotation
  • Solution-phase reaction profile

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

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