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

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

doi:10.1002/chir.23400

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

Chirality. 2022 Feb;34(2):317-324. doi: 10.1002/chir.23400. Epub 2021 Dec 22.

Authors

Qingyu Wang¹, Adriana Pietropaolo², Mariagrazia Fortino², Zhiyi Song¹, Masayoshi Bando¹, Naofumi Naga³, Tamaki Nakano^{1

4}

Affiliations

¹ Institute for Catalysis (ICAT) and Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo, Japan.
² Dipartimento di Scienze della Salute, Università di Catanzaro, Catanzaro, Italy.
³ Department of Applied Chemistry, College of Engineering, Shibaura Institute of Technology, Tokyo, Japan.
⁴ Integrated Research Consortium on Chemical Sciences (IRCCS), Institute for Catalysis, Hokkaido University, Sapporo, Japan.

PMID: 34939234
DOI: 10.1002/chir.23400

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.

Keywords: axial chirality; excited states; proton transfer; rotational energy barrier; twisted-coplanar transition.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromatography, High Pressure Liquid
Naphthalenes*
Stereoisomerism

Substances

Naphthalenes
1,1'-binaphthyl

Abstract

Publication types

MeSH terms

Substances

Grants and funding