The effect of conformational equilibrium on rate of reactions involving neighbouring group participation

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Abstract

The hydrolysis reaction of condensed bromoalkylphthalazinones type 4 is efficiently assisted by the neighbouring hydrazinocarbonyl group. The expected order of anchimeric assistance has been found to be dependent on the chain length. The relatively large values of rate constants are due to an entropy effect firmly supported by computed analysis of the conformational equilibria for the bromoethyl chain appended to phthalazinone (1a) and 2,3-dihydroimidazo [2,1-a] phthalazinone (4a), respectively. The results of this analysis are in good agreement with the activation entropy values.

Original languageEnglish
Pages (from-to)1507-1514
Number of pages8
JournalTetrahedron
Volume48
Issue number8
DOIs
Publication statusPublished - Feb 21 1992

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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