PlumX Metrics
Embed PlumX Metrics

A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles

New Journal of Chemistry, ISSN: 1369-9261, Vol: 31, Issue: 1, Page: 144-154
2007
  • 53
    Citations
  • 0
    Usage
  • 43
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    53
    • Citation Indexes
      53
  • Captures
    43

Article Description

Functionalized 2-formylphenylboronic acids undergo an unprecedented tautomeric rearrangement in solution to form corresponding 1,3-dihydro-1,3- dihydroxybenzo[c][2,1]oxaboroles. X-Ray analyses of selected examples revealed diverse solid-state molecular structures from a planar open form with a hydrogen-bonded carbonyl group (X = 3-F) through a twisted conformer showing a weak carbonyl-boron interaction (X = 3,5-Br) to a cyclic oxaborole derivative (X = 3-Br). Variable-temperature H NMR spectroscopy was used to determine equilibrium constants as well as enthalpies and entropies of tautomerization in a mixed solvent [D]acetone-DO (95:5). A computational approach to the process by DFT (B3LYP) and MP2 methods has also been performed. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Bibliographic Details

Provide Feedback

Have ideas for a new metric? Would you like to see something else here?Let us know