Proton-driven conformational change in a 2-aryl-p-carborane constrained by an intramolecular C-H⋯O hydrogen bond

Kiminori Ohta, Hiroto Yamazaki, Masatoshi Kawahata, Kentaro Yamaguchi, Fabio Pichierri, Yasuyuki Endo

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

2-(2-Hydroxyphenyl)-p-carborane forms an intramolecular hydrogen bonding based on the results of X-ray, IR, and 1H NMR studies. The hydrogen bonding is released by the addition of acid in solution. Density functional theory (DFT) calculations on the phenol, phenolate and protonated phenol structures indicated two stable conformational state, hydrogen bonding form for phenol and phenolate, and dihydrogen bonding form for protonated phenol.

Original languageEnglish
Pages (from-to)5231-5234
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number30
DOIs
Publication statusPublished - 2007 Jul 23

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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