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

98 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

Access to Document

10.1021/ol034581j

Cite this

@article{4405f6639a6a40f68b22d50fe4d43715,

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",

month = jul,

day = "10",

doi = "10.1021/ol034581j",

language = "English (US)",

volume = "5",

pages = "2421--2424",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=0141631428&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0141631428&partnerID=8YFLogxK

U2 - 10.1021/ol034581j

DO - 10.1021/ol034581j

M3 - Article

C2 - 12841745

AN - SCOPUS:0141631428

SN - 1523-7060

VL - 5

SP - 2421

EP - 2424

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

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this