Photo racemization of 2,2′-dihydroxy-1,1′-binaphthyl derivatives

Qingyu Wang, Adriana Pietropaolo, Mariagrazia Fortino, Zhiyi Song, Masayoshi Bando, Naofumi Naga, Tamaki Nakano

Research output: Contribution to journalArticlepeer-review

Abstract

Photo racemization of 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) and its monomethyl ether, monobutyl ether, and dimethyl ether was studied by means of circularly dichroism spectra, chiral HPLC, and theoretical calculations of rotation energy barriers. Racemization was fastest for BINOL and about one seventh as fast for the monomethyl and monobutyl ethers while it was too slow to be detected for the dimethyl ether under the present conditions.

Original languageEnglish
JournalChirality
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • axial chirality
  • excited states
  • proton transfer
  • rotational energy barrier
  • twisted-coplanar transition

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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