Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]
Abstract
Abstract Naphthalene oxidation with metal–oxygen intermediates is a difficult reaction in environmental and biological chemistry. Herein, we report that a Mn IV bis(hydroxo) complex, which was fully characterized by various physicochemical methods, such as ESI‐MS, UV/Vis, and EPR analysis, X‐ray diffraction, and XAS, can be employed for the oxidation of naphthalene in the presence of acid to afford 1,4‐naphthoquinone. Redox titration of the Mn IV bis(hydroxo) complex gave a one‐electron reduction potential of 1.09 V, which is the most positive potential for all reported nonheme Mn IV bis(hydroxo) species as well as Mn IV oxo analogues. Kinetic studies, including kinetic isotope effect analysis, suggest that the naphthalene oxidation occurs through a rate‐determining electron transfer process.
- Authors:
-
[1]
- DGIST, Daegu (Korea)
- Stanford Univ., Stanford, CA (United States)
- Stanford Synchrotron Radiation Lab., Menlo Park, CA (United States)
- Stanford Univ., Stanford, CA (United States); Stanford Synchrotron Radiation Lab., Menlo Park, CA (United States)
- Publication Date:
- Research Org.:
- SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1469755
- Alternate Identifier(s):
- OSTI ID: 1438278
- Grant/Contract Number:
- 2017R1A2B4005441; DGIST R&D Program 18-BD-0403; 2016M3D3A01913243; GM-40392; P41GM103393; AC02-76SF00515
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 57; Journal Issue: 26; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; manganese; metal–hydroxo compounds; naphthalene; oxidation; reaction mechanisms
Citation Formats
Jeong, Donghyun, Yan, James J., Noh, Hyeonju, Hedman, Britt, Hodgson, Keith O., Solomon, Edward I., and Cho, Jaeheung. Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]. United States: N. p., 2018.
Web. doi:10.1002/anie.201802641.
Jeong, Donghyun, Yan, James J., Noh, Hyeonju, Hedman, Britt, Hodgson, Keith O., Solomon, Edward I., & Cho, Jaeheung. Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]. United States. https://doi.org/10.1002/anie.201802641
Jeong, Donghyun, Yan, James J., Noh, Hyeonju, Hedman, Britt, Hodgson, Keith O., Solomon, Edward I., and Cho, Jaeheung. Fri .
"Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]". United States. https://doi.org/10.1002/anie.201802641. https://www.osti.gov/servlets/purl/1469755.
@article{osti_1469755,
title = {Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]},
author = {Jeong, Donghyun and Yan, James J. and Noh, Hyeonju and Hedman, Britt and Hodgson, Keith O. and Solomon, Edward I. and Cho, Jaeheung},
abstractNote = {Abstract Naphthalene oxidation with metal–oxygen intermediates is a difficult reaction in environmental and biological chemistry. Herein, we report that a Mn IV bis(hydroxo) complex, which was fully characterized by various physicochemical methods, such as ESI‐MS, UV/Vis, and EPR analysis, X‐ray diffraction, and XAS, can be employed for the oxidation of naphthalene in the presence of acid to afford 1,4‐naphthoquinone. Redox titration of the Mn IV bis(hydroxo) complex gave a one‐electron reduction potential of 1.09 V, which is the most positive potential for all reported nonheme Mn IV bis(hydroxo) species as well as Mn IV oxo analogues. Kinetic studies, including kinetic isotope effect analysis, suggest that the naphthalene oxidation occurs through a rate‐determining electron transfer process.},
doi = {10.1002/anie.201802641},
journal = {Angewandte Chemie (International Edition)},
number = 26,
volume = 57,
place = {United States},
year = {2018},
month = {4}
}
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