
Bulletin of the Chemical Society of Japan p. 609 - 617 (1998)
Update date:2022-08-03
Topics:
Uehara, Minori
Urade, Mika
Abe, Yuriko
The preparation of [Mn(saltnOCOPh)Cl]·DMF (H2saltnOCOPh: N,N'-(2-benzoyloxypropane-1,3-diyl)bis(salicylideneamine)) and kinetics and mechanisms of H2O2 disproportionation catalyzed by mononucleur Schiff base manganese(III) complexes, such as [Mn(salen)Cl) (H2salen: N,N'-ethylenebis(salicylideneamine)), [Mn(saltn)Cl] (H2saltn: N,N'-propane- 1,3-diylbis(salicylideneamine)), [Mn(saltnOH)Cl] (H2saltnOH: N,N'-(2-hydroxypropane-1,3-diyl)bis(salicylideneamine)), and [Mn(saltnOCOPh)Cl] in N,N'-dimethylformamide (DMF), have been investigated. The disproportionation of H2O2 to O2 and H2O proceeds coupled with the redox cycle between the Mn(III) complex and the Mn(IV) intermediate: The first step is the fast equilibrium (Km) of the Mn(III) complex and the Mn(IV) intermediate formed by the reaction of the Mn(III) complex with H2O2, followed by a slow reaction (k1) of the Mn(IV) intermediate with H2O2 to produce O2 and H2O recovering the original Mn(III) complex. The Km values decrease in the following order: [Mn(salen)Cl] (728 mol-1 dm3) ? [Mn(saltnOH)CI] (28.0 mol-1 dm3) > [Mn(saltn)Cl] (6.28 mol-1 dm3) > [Mn(saltnOCOPh)Cl] (1.83 mol-1 dm3), reflecting an increased distortion along the axis containing the coordination of H2O2 to the Mn(III) complex. On the other hand, the rate constants (k1) fall into the following sequences: [Mn(saltnOH)Cl] (4.29 × 105 mol-2dm6s-1) > [Mn(salen)Cl] (1.67 × 105 mol-2 dm6 s-1) > [Mn(saltnOCOPh)Cl] (3.34 × 104 mol-2 dm6 s-1) > [Mn(salen)Cl] (6.15 × 103 mol-2 dm6 s-1). In spite of the small Km values for saltnOH, saltnOCOPh, and saltn complexes with the 1,3-diamine ligand, compared to that for the salen complex, the large kl value for the saltnOH complex strongly suggests stabilization of the transition state for the formation of hydrogen-bondings among the Mn(IV) intermediates and H2O2. Futhermore, the effect of the OH- ion on the H2O2 disproportionation catalyzed by [Mn(salen)Cl] has been reported. On account of the formation of [Mn(salen)OH] coordinated by the OH- ion, the appearance of the reaction path involving not only the Mn(III)-Mn(IV) cycle, but also the Mn(II)-Mn(III) cycle, is shown based on the ESR and visible spectral studies. The activity for the Mn(II)-Mn(III) cycle is 20 times larger than that for the Mn(III)-Mn(IV) cycle.
Xiamen XM-Innovation Chemical Co., Ltd
Contact:+86-592-3216205
Address:Unit Q, 11/F, No.1 Office Building, Wuyuan Bay Business Center, Huli District, Xiamen City, Fujian Province, P.R.C
Shanghai SMEC Trading Co., Ltd.
website:http://www.shanghaismec.com
Contact:+86-21-68811293
Address:ROOM 1101,NO.800 SHANGCHENG RD,SHANGHAI,CHINA
Qingdao Kingway Pharmtech Co., Ltd.
Contact:86-532-87118899
Address:No. 88, Middle Haixi Road, Jiaonan City, Qingdao, China
Changzhou Sunlight Pharmaceutical Co., Ltd.
Contact:+86-519-83131668;83139028;83138042;83137041
Address:JiuliStreet, Benniu Town Changzhou City, Jiangsu Province
Ji'nan Orgachem Pharmaceutical Co.,Ltd
Contact:+86-531-82687810
Address:Jinan
Doi:10.1016/0022-1902(68)80465-8
(1968)Doi:10.1021/ol990908y
(1999)Doi:10.1007/BF00470253
()Doi:10.1021/jo201320g
(2011)Doi:10.1007/s00044-011-9735-9
(2012)Doi:10.1021/jm9005115
(2009)