Detecting solid-state reactivity in 10-hydroxy-10,9-boroxophenanthrene using NMR spectroscopy

Diego Carnevale, Vicente Del Amo, Douglas Philp*, Sharon E. Ashbrook

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Solid-state NMR spectroscopy and computational methods are used to probe the transformation of 10-hydroxy-10,9-boroxophenanthrene to its corresponding anhydride in the solid state. DFT calculations are used to assist the assignment of the NMR spectra of both these boron-containing heteroaromatic compounds, in solution and in the solid state. Solid-state NMR spectroscopy reveals that the dehydration of crystalline 10-hydroxy-10,9-boroxophenanthrene proceeds at relatively low temperatures - a transformation, that is, undetectable by X-ray diffraction and gravimetric analysis. Computational methods are used to elucidate a plausible reaction pathway for this transformation and to explain its detection only by NMR methods.

Original languageEnglish (US)
Pages (from-to)6238-6250
Number of pages13
JournalTetrahedron
Volume66
Issue number32
DOIs
StatePublished - Aug 7 2010

Keywords

  • Aromatic compounds
  • DFT calculations
  • Molecular recognition
  • Reversible reactions
  • Self-assembly
  • Solid-state NMR spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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