Rate-Determining Water-Assisted O–O Bond Cleavage of an FeIII-OOH Intermediate in a Bio-inspired Nonheme Iron-Catalyzed Oxidation
Publication type: Journal Article
Publication date: 2013-04-19
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
23594282
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Hydrocarbon oxidations by bio-inspired nonheme iron catalysts and H2O2 have been proposed to involve an Fe(III)-OOH intermediate that decays via a water-assisted mechanism to form an Fe(V)(O)(OH) oxidant. Herein we report kinetic evidence for this pathway in the oxidation of 1-octene catalyzed by [Fe(II)(TPA)(NCCH3)](2+) (1, TPA = tris(2-pyridylmethyl)amine). The (TPA)Fe(III)(OOH) intermediate 2 can be observed at -40 °C and is found to undergo first-order decay, which is accelerated by water. Interestingly, the decay rate of 2 is comparable to that of product formation, indicating that the decay of 2 results in olefin oxidation. Furthermore, the Eyring activation parameters for the decay of 2 and product formation are identical, and both processes are associated with an H2O/D2O KIE of 2.5. Taken together with previous (18)O-labeling data, these results point to a water-assisted heterolytic O-O bond cleavage of 2 as the rate-limiting step in olefin oxidation.
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Oloo W. N., Fielding A. J., Que, Jr. L. Rate-Determining Water-Assisted O–O Bond Cleavage of an FeIII-OOH Intermediate in a Bio-inspired Nonheme Iron-Catalyzed Oxidation // Journal of the American Chemical Society. 2013. Vol. 135. No. 17. pp. 6438-6441.
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Oloo W. N., Fielding A. J., Que, Jr. L. Rate-Determining Water-Assisted O–O Bond Cleavage of an FeIII-OOH Intermediate in a Bio-inspired Nonheme Iron-Catalyzed Oxidation // Journal of the American Chemical Society. 2013. Vol. 135. No. 17. pp. 6438-6441.
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RIS
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TY - JOUR
DO - 10.1021/ja402759c
UR - https://doi.org/10.1021/ja402759c
TI - Rate-Determining Water-Assisted O–O Bond Cleavage of an FeIII-OOH Intermediate in a Bio-inspired Nonheme Iron-Catalyzed Oxidation
T2 - Journal of the American Chemical Society
AU - Oloo, Williamson N
AU - Fielding, Andrew J
AU - Que, Jr., Lawrence
PY - 2013
DA - 2013/04/19
PB - American Chemical Society (ACS)
SP - 6438-6441
IS - 17
VL - 135
PMID - 23594282
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2013_Oloo,
author = {Williamson N Oloo and Andrew J Fielding and Lawrence Que, Jr.},
title = {Rate-Determining Water-Assisted O–O Bond Cleavage of an FeIII-OOH Intermediate in a Bio-inspired Nonheme Iron-Catalyzed Oxidation},
journal = {Journal of the American Chemical Society},
year = {2013},
volume = {135},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/ja402759c},
number = {17},
pages = {6438--6441},
doi = {10.1021/ja402759c}
}
Cite this
MLA
Copy
Oloo, Williamson N., et al. “Rate-Determining Water-Assisted O–O Bond Cleavage of an FeIII-OOH Intermediate in a Bio-inspired Nonheme Iron-Catalyzed Oxidation.” Journal of the American Chemical Society, vol. 135, no. 17, Apr. 2013, pp. 6438-6441. https://doi.org/10.1021/ja402759c.