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Title: Electronic Structural Analysis of Copper(II)–TEMPO/ABNO Complexes Provides Evidence for Copper(I)–Oxoammonium Character

Abstract

Copper/aminoxyl species are proposed as key intermediates in aerobic alcohol oxidation. Several possible electronic structural descriptions of these species are possible, and here we probe this issue by examining four crystallographically characterized Cu/aminoxyl halide complexes by Cu K-edge, Cu L2,3- edge, and Cl K-edge X-ray absorption spectroscopy. The mixing coefficients between Cu, aminoxyl, and halide orbitals are determined via these techniques with support from density functional theory. The emergent electronic structure picture reveals that Cu coordination confers appreciable oxoammonium character to the aminoxyl ligand. The computational methodology is extended to one of the putative intermediates invoked in catalytic Cu/aminoxyl-driven alcohol oxidation reactions, with similar findings. On the whole, the results have important implications for the mechanism of alcohol oxidation and the underlying basis for cooperativity in this co- catalyst system.

Authors:
 [1];  [2];  [1];  [1]; ORCiD logo [2]; ORCiD logo [1]
+ Show Author Affiliations
  1. Cornell Univ., Ithaca, NY (United States). Dept. of Chemistry and Chemical Biology
  2. Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemistry
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER); National Institutes of Health (NIH)
OSTI Identifier:
1395532
Grant/Contract Number:  
FG02-05ER15690; AC02-76SF00515; P41GM103393
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 139; Journal Issue: 38; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Walroth, Richard C., Miles, Kelsey C., Lukens, James T., MacMillan, Samantha N., Stahl, Shannon S., and Lancaster, Kyle M. Electronic Structural Analysis of Copper(II)–TEMPO/ABNO Complexes Provides Evidence for Copper(I)–Oxoammonium Character. United States: N. p., 2017. Web. doi:10.1021/jacs.7b07186.
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Walroth, Richard C., Miles, Kelsey C., Lukens, James T., MacMillan, Samantha N., Stahl, Shannon S., & Lancaster, Kyle M. Electronic Structural Analysis of Copper(II)–TEMPO/ABNO Complexes Provides Evidence for Copper(I)–Oxoammonium Character. United States. https://doi.org/10.1021/jacs.7b07186
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Walroth, Richard C., Miles, Kelsey C., Lukens, James T., MacMillan, Samantha N., Stahl, Shannon S., and Lancaster, Kyle M. Mon . "Electronic Structural Analysis of Copper(II)–TEMPO/ABNO Complexes Provides Evidence for Copper(I)–Oxoammonium Character". United States. https://doi.org/10.1021/jacs.7b07186. https://www.osti.gov/servlets/purl/1395532.
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@article{osti_1395532,
title = {Electronic Structural Analysis of Copper(II)–TEMPO/ABNO Complexes Provides Evidence for Copper(I)–Oxoammonium Character},
author = {Walroth, Richard C. and Miles, Kelsey C. and Lukens, James T. and MacMillan, Samantha N. and Stahl, Shannon S. and Lancaster, Kyle M.},
abstractNote = {Copper/aminoxyl species are proposed as key intermediates in aerobic alcohol oxidation. Several possible electronic structural descriptions of these species are possible, and here we probe this issue by examining four crystallographically characterized Cu/aminoxyl halide complexes by Cu K-edge, Cu L2,3- edge, and Cl K-edge X-ray absorption spectroscopy. The mixing coefficients between Cu, aminoxyl, and halide orbitals are determined via these techniques with support from density functional theory. The emergent electronic structure picture reveals that Cu coordination confers appreciable oxoammonium character to the aminoxyl ligand. The computational methodology is extended to one of the putative intermediates invoked in catalytic Cu/aminoxyl-driven alcohol oxidation reactions, with similar findings. On the whole, the results have important implications for the mechanism of alcohol oxidation and the underlying basis for cooperativity in this co- catalyst system.},
doi = {10.1021/jacs.7b07186},
journal = {Journal of the American Chemical Society},
number = 38,
volume = 139,
place = {United States},
year = {Mon Sep 18 00:00:00 EDT 2017},
month = {Mon Sep 18 00:00:00 EDT 2017}
}
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https://doi.org/10.1021/jacs.7b07186
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