Catalytic O-O activation chemistry mediated by iron hangman porphyrins with a wide range of proton-donating abilities

Leng Leng Chng; Christopher J. Chang; Daniel G. Nocera

doi:10.1021/ol034581j

Catalytic O-O activation chemistry mediated by iron hangman porphyrins with a wide range of proton-donating abilities

Leng Leng Chng
, Christopher J. Chang
, Daniel G. Nocera

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

100 Scopus citations

Abstract

(Matrix presented) A library of hanging porphyrin xanthene (HPX) compounds containing pendant groups with various proton-donating abilities (pK _a ranging from ∼2 to 25) has been synthesized. Their corresponding chloroiron(III) complexes promote the catalase-like disproportionation of hydrogen peroxide. The overall activity and turnover numbers (TONs) are maximal for iron HPX complexes bearing acidic hydrogen-bond pendants. These results establish that careful control of intramolecular proton inventory can dramatically influence the catalytic activation of O-O bonds.

Original language	English (US)
Pages (from-to)	2421-2424
Number of pages	4
Journal	Organic letters
Volume	5
Issue number	14
DOIs	https://doi.org/10.1021/ol034581j
State	Published - Jul 10 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol034581j

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title = "Catalytic O-O activation chemistry mediated by iron hangman porphyrins with a wide range of proton-donating abilities",

abstract = "(Matrix presented) A library of hanging porphyrin xanthene (HPX) compounds containing pendant groups with various proton-donating abilities (pK a ranging from ∼2 to 25) has been synthesized. Their corresponding chloroiron(III) complexes promote the catalase-like disproportionation of hydrogen peroxide. The overall activity and turnover numbers (TONs) are maximal for iron HPX complexes bearing acidic hydrogen-bond pendants. These results establish that careful control of intramolecular proton inventory can dramatically influence the catalytic activation of O-O bonds.",

author = "Chng, \{Leng Leng\} and Chang, \{Christopher J.\} and Nocera, \{Daniel G.\}",

year = "2003",

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doi = "10.1021/ol034581j",

language = "English (US)",

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journal = "Organic letters",

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T1 - Catalytic O-O activation chemistry mediated by iron hangman porphyrins with a wide range of proton-donating abilities

AU - Chng, Leng Leng

AU - Chang, Christopher J.

AU - Nocera, Daniel G.

PY - 2003/7/10

Y1 - 2003/7/10

N2 - (Matrix presented) A library of hanging porphyrin xanthene (HPX) compounds containing pendant groups with various proton-donating abilities (pK a ranging from ∼2 to 25) has been synthesized. Their corresponding chloroiron(III) complexes promote the catalase-like disproportionation of hydrogen peroxide. The overall activity and turnover numbers (TONs) are maximal for iron HPX complexes bearing acidic hydrogen-bond pendants. These results establish that careful control of intramolecular proton inventory can dramatically influence the catalytic activation of O-O bonds.

AB - (Matrix presented) A library of hanging porphyrin xanthene (HPX) compounds containing pendant groups with various proton-donating abilities (pK a ranging from ∼2 to 25) has been synthesized. Their corresponding chloroiron(III) complexes promote the catalase-like disproportionation of hydrogen peroxide. The overall activity and turnover numbers (TONs) are maximal for iron HPX complexes bearing acidic hydrogen-bond pendants. These results establish that careful control of intramolecular proton inventory can dramatically influence the catalytic activation of O-O bonds.

UR - https://www.scopus.com/pages/publications/0141631428

UR - https://www.scopus.com/pages/publications/0141631428#tab=citedBy

U2 - 10.1021/ol034581j

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M3 - Article

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AN - SCOPUS:0141631428

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SP - 2421

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JO - Organic letters

JF - Organic letters

IS - 14

ER -

Catalytic O-O activation chemistry mediated by iron hangman porphyrins with a wide range of proton-donating abilities

Abstract

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