Exchange of quinone and hydroquinone moieties in mixed solutions of biquinone and bihydroquinone

Naoto Hayashi; Kiyomi Matsui; Akifumi Kanda; Takahiro Yoshikawa; Hiroyuki Nakagawa; Junro Yoshino; Hiroyuki Higuchi

doi:10.1246/cl.2011.947

Exchange of quinone and hydroquinone moieties in mixed solutions of biquinone and bihydroquinone

Naoto Hayashi^*, Kiyomi Matsui, Akifumi Kanda, Takahiro Yoshikawa, Hiroyuki Nakagawa, Junro Yoshino, Hiroyuki Higuchi

^*Corresponding author for this work

Program of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

A mixture of biquinone (QQn) and bihydroquinone (HHn) bearing tert-butyl substituents at 5,5'- (n = 1) and 6,6'-positions (n = 2) yields hydroquinonylquinone (HQn) as an equilibrium product by quinone/hydroquinone exchange. The equilibrium constants for the formation of HQ1 are higher than those of HQ2 in all solvents. While the exchange between QQ1 and HH1 is slow, that between HQ1s occurs so rapidly in CDCl₃ that it is observed in phase-sensitive 2DNOESYNMR spectra.

Original language	English
Pages (from-to)	947-949
Number of pages	3
Journal	Chemistry Letters
Volume	40
Issue number	9
DOIs	https://doi.org/10.1246/cl.2011.947
State	Published - 2011

ASJC Scopus subject areas

General Chemistry

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title = "Exchange of quinone and hydroquinone moieties in mixed solutions of biquinone and bihydroquinone",

abstract = "A mixture of biquinone (QQn) and bihydroquinone (HHn) bearing tert-butyl substituents at 5,5'- (n = 1) and 6,6'-positions (n = 2) yields hydroquinonylquinone (HQn) as an equilibrium product by quinone/hydroquinone exchange. The equilibrium constants for the formation of HQ1 are higher than those of HQ2 in all solvents. While the exchange between QQ1 and HH1 is slow, that between HQ1s occurs so rapidly in CDCl3 that it is observed in phase-sensitive 2DNOESYNMR spectra.",

author = "Naoto Hayashi and Kiyomi Matsui and Akifumi Kanda and Takahiro Yoshikawa and Hiroyuki Nakagawa and Junro Yoshino and Hiroyuki Higuchi",

year = "2011",

doi = "10.1246/cl.2011.947",

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T1 - Exchange of quinone and hydroquinone moieties in mixed solutions of biquinone and bihydroquinone

AU - Hayashi, Naoto

AU - Matsui, Kiyomi

AU - Kanda, Akifumi

AU - Yoshikawa, Takahiro

AU - Nakagawa, Hiroyuki

AU - Yoshino, Junro

AU - Higuchi, Hiroyuki

PY - 2011

Y1 - 2011

N2 - A mixture of biquinone (QQn) and bihydroquinone (HHn) bearing tert-butyl substituents at 5,5'- (n = 1) and 6,6'-positions (n = 2) yields hydroquinonylquinone (HQn) as an equilibrium product by quinone/hydroquinone exchange. The equilibrium constants for the formation of HQ1 are higher than those of HQ2 in all solvents. While the exchange between QQ1 and HH1 is slow, that between HQ1s occurs so rapidly in CDCl3 that it is observed in phase-sensitive 2DNOESYNMR spectra.

AB - A mixture of biquinone (QQn) and bihydroquinone (HHn) bearing tert-butyl substituents at 5,5'- (n = 1) and 6,6'-positions (n = 2) yields hydroquinonylquinone (HQn) as an equilibrium product by quinone/hydroquinone exchange. The equilibrium constants for the formation of HQ1 are higher than those of HQ2 in all solvents. While the exchange between QQ1 and HH1 is slow, that between HQ1s occurs so rapidly in CDCl3 that it is observed in phase-sensitive 2DNOESYNMR spectra.

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DO - 10.1246/cl.2011.947

M3 - 学術論文

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SN - 0366-7022

VL - 40

SP - 947

EP - 949

JO - Chemistry Letters

JF - Chemistry Letters

IS - 9

ER -

Exchange of quinone and hydroquinone moieties in mixed solutions of biquinone and bihydroquinone

Abstract

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