Chemical mechanism of dioxygen activation by manganese(III) Schiff base compound in the presence of aliphatic aldehydes

Miyuki Suzuki; Takashi Ishikawa; Akihiko Harada; Shigeru Ohba; Masatomi Sakamoto; Yuzo Nishida

doi:10.1016/S0277-5387(97)00003-X

Chemical mechanism of dioxygen activation by manganese(III) Schiff base compound in the presence of aliphatic aldehydes

Miyuki Suzuki, Takashi Ishikawa, Akihiko Harada, Shigeru Ohba, Masatomi Sakamoto, Yuzo Nishida

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

34 Citations (Scopus)

Abstract

The manganese(III) complexes with tetradentate Schiff base [H₂(L)] derived from salicylaldehyde and 2-amino-1-benzylamine [abbreviated as H₂(salabza)], ethylenedimaineand 2-hydroxybenzophenone [H₂(7-Phe-salen)], ethylenediamine and 2-hydroxyacetophenone [H₂(7-Me-salen)] showed much higher activity for degradation of tetraphenylcyclopentadienone(TCPN) the singlet oxygen (¹Δ_g) scavenger, in the presence of cyclohexanecarboxaldehyde than those of the compounds with H₂(salen) and H₂(salphen), which are derived from salicyaldehyde and ethylenediamine, and o-phenylenediamine, respectively. X-ray crystal structural determinations of the former three compounds and electrochemical data of all the compounds have given strong support for the conclusion that the active species for degradation of TCPN is an acylperoxo Mn^III species coordinated by an aliphatic peracid chelate, which should be derived from aliphatic aldehyde and dioxygen, where the geometry of the tetradentate Schiff base around the Mn^III ion is of cis-β-configuration. Under the same experimental conditions, the corresponding iron(III) compounds exhibited negligible activity towards the activation of the dioxygen molecule. This was explained in terms of the difference in electronic structures between the two metal ions.

Original language	English
Pages (from-to)	2553-2561
Number of pages	9
Journal	Polyhedron
Volume	16
Issue number	15
DOIs	https://doi.org/10.1016/S0277-5387(97)00003-X
Publication status	Published - 1997
Externally published	Yes

Keywords

Activation of dioxygen
Dioxygen and aldehyde
Mn(III) Schiff base compounds
Mn(III) and Fe(III) compounds

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0277-5387(97)00003-X

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title = "Chemical mechanism of dioxygen activation by manganese(III) Schiff base compound in the presence of aliphatic aldehydes",

abstract = "The manganese(III) complexes with tetradentate Schiff base [H2(L)] derived from salicylaldehyde and 2-amino-1-benzylamine [abbreviated as H2(salabza)], ethylenedimaineand 2-hydroxybenzophenone [H2(7-Phe-salen)], ethylenediamine and 2-hydroxyacetophenone [H2(7-Me-salen)] showed much higher activity for degradation of tetraphenylcyclopentadienone(TCPN) the singlet oxygen (1Δg) scavenger, in the presence of cyclohexanecarboxaldehyde than those of the compounds with H2(salen) and H2(salphen), which are derived from salicyaldehyde and ethylenediamine, and o-phenylenediamine, respectively. X-ray crystal structural determinations of the former three compounds and electrochemical data of all the compounds have given strong support for the conclusion that the active species for degradation of TCPN is an acylperoxo MnIII species coordinated by an aliphatic peracid chelate, which should be derived from aliphatic aldehyde and dioxygen, where the geometry of the tetradentate Schiff base around the MnIII ion is of cis-β-configuration. Under the same experimental conditions, the corresponding iron(III) compounds exhibited negligible activity towards the activation of the dioxygen molecule. This was explained in terms of the difference in electronic structures between the two metal ions.",

keywords = "Activation of dioxygen, Dioxygen and aldehyde, Mn(III) Schiff base compounds, Mn(III) and Fe(III) compounds",

author = "Miyuki Suzuki and Takashi Ishikawa and Akihiko Harada and Shigeru Ohba and Masatomi Sakamoto and Yuzo Nishida",

year = "1997",

doi = "10.1016/S0277-5387(97)00003-X",

language = "English",

volume = "16",

pages = "2553--2561",

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T1 - Chemical mechanism of dioxygen activation by manganese(III) Schiff base compound in the presence of aliphatic aldehydes

AU - Suzuki, Miyuki

AU - Ishikawa, Takashi

AU - Harada, Akihiko

AU - Ohba, Shigeru

AU - Sakamoto, Masatomi

AU - Nishida, Yuzo

PY - 1997

Y1 - 1997

N2 - The manganese(III) complexes with tetradentate Schiff base [H2(L)] derived from salicylaldehyde and 2-amino-1-benzylamine [abbreviated as H2(salabza)], ethylenedimaineand 2-hydroxybenzophenone [H2(7-Phe-salen)], ethylenediamine and 2-hydroxyacetophenone [H2(7-Me-salen)] showed much higher activity for degradation of tetraphenylcyclopentadienone(TCPN) the singlet oxygen (1Δg) scavenger, in the presence of cyclohexanecarboxaldehyde than those of the compounds with H2(salen) and H2(salphen), which are derived from salicyaldehyde and ethylenediamine, and o-phenylenediamine, respectively. X-ray crystal structural determinations of the former three compounds and electrochemical data of all the compounds have given strong support for the conclusion that the active species for degradation of TCPN is an acylperoxo MnIII species coordinated by an aliphatic peracid chelate, which should be derived from aliphatic aldehyde and dioxygen, where the geometry of the tetradentate Schiff base around the MnIII ion is of cis-β-configuration. Under the same experimental conditions, the corresponding iron(III) compounds exhibited negligible activity towards the activation of the dioxygen molecule. This was explained in terms of the difference in electronic structures between the two metal ions.

AB - The manganese(III) complexes with tetradentate Schiff base [H2(L)] derived from salicylaldehyde and 2-amino-1-benzylamine [abbreviated as H2(salabza)], ethylenedimaineand 2-hydroxybenzophenone [H2(7-Phe-salen)], ethylenediamine and 2-hydroxyacetophenone [H2(7-Me-salen)] showed much higher activity for degradation of tetraphenylcyclopentadienone(TCPN) the singlet oxygen (1Δg) scavenger, in the presence of cyclohexanecarboxaldehyde than those of the compounds with H2(salen) and H2(salphen), which are derived from salicyaldehyde and ethylenediamine, and o-phenylenediamine, respectively. X-ray crystal structural determinations of the former three compounds and electrochemical data of all the compounds have given strong support for the conclusion that the active species for degradation of TCPN is an acylperoxo MnIII species coordinated by an aliphatic peracid chelate, which should be derived from aliphatic aldehyde and dioxygen, where the geometry of the tetradentate Schiff base around the MnIII ion is of cis-β-configuration. Under the same experimental conditions, the corresponding iron(III) compounds exhibited negligible activity towards the activation of the dioxygen molecule. This was explained in terms of the difference in electronic structures between the two metal ions.

KW - Activation of dioxygen

KW - Dioxygen and aldehyde

KW - Mn(III) Schiff base compounds

KW - Mn(III) and Fe(III) compounds

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VL - 16

SP - 2553

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JO - Polyhedron

JF - Polyhedron

IS - 15

ER -

Chemical mechanism of dioxygen activation by manganese(III) Schiff base compound in the presence of aliphatic aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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