title: Protonation Behavior of 1,1'-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization.
abstract: The behavior of 1,1'-bi-2-naphthol (BINOL) in variety of (super)acid media has been studied by NMR. The results are combined with the theoretical (DFT) study of the role of mono- and diprotonated forms of BINOL in the acid-catalyzed atropisomerization of this compound. It is demonstrated that the process of enantiomeric configuration exchange proceeds mainly via internal rotation around the C1(sp3)-C1'(sp3) bond in intermediates such as C1-monoprotonated keto or C1,C1'-diprotonated forms of BINOL, depending on the acidity level.
authors.affiliation: N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry , Pr. Akademika Lavrentieva 9, Novosibirsk 630090, Russia.
authors.forename: Alexander M
authors.initials: AM
authors.lastname: Genaev
authors.affiliation: N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry , Pr. Akademika Lavrentieva 9, Novosibirsk 630090, Russia.|Novosibirsk State University , Pirogova 2, Novosibirsk 630090, Russia.
authors.forename: George E
authors.initials: GE
authors.lastname: Salnikov
authors.affiliation: N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry , Pr. Akademika Lavrentieva 9, Novosibirsk 630090, Russia.
authors.forename: Andrey V
authors.initials: AV
authors.lastname: Shernyukov
authors.affiliation: Novosibirsk State University , Pirogova 2, Novosibirsk 630090, Russia.
authors.forename: Zhongwei
authors.initials: Z
authors.lastname: Zhu
authors.affiliation: Novosibirsk State University , Pirogova 2, Novosibirsk 630090, Russia.|Boreskov Institute of Catalysis , Pr. Akademika Lavrentieva 5, Novosibirsk 630090, Russia.
authors.forename: Konstantin Yu
authors.identifier: 0000-0002-9466-1592
authors.initials: KY
authors.lastname: Koltunov