The metal-complexing properties of N-benzoyl-N-phenylhydroxylamine derivatives containing N-phenyl ring substituents

Vernon, F.; Gunawardhana, H.D.

doi:10.1016/s0003-2670(01)84064-2

Cited by 13 publications

(4 citation statements)

References 9 publications

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“…Bis(4-nitrophenyl)phosphate(BNPP) and the buffer [tris(hydroxymethyl)aminomethane] were purchased from Sigma Chemical Co. The following compounds were prepared according to the literature: 4¢-(x-chloroformylvaleryl)benzo-15-crown-5 [12], N-phenylhydroxylamine [13]. The BNPP stock solution for kinetics was prepared using redistilled deionized H 2 O.…”

Section: General Methods and Materialsmentioning

confidence: 99%

Studies on the reaction kinetics and the mechanism of hydrolysis of bis(4-nitrophenyl)phosphate (BNPP) by hydroxamic acid complexes containing benzo-15-crown-5

Zhou

et al. 2005

Transition Met Chem

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A hydroxamic acid (HL) containing benzo-15-crown-5 and their copper(II), zinc(II), cobalt(II) and manganese(II) complexes have been synthesized and studied as catalysts for the cleavage of bis(4-nitrophenyl)phosphate (BNPP). The catalytic properties of these complexes and the kinetics and mechanism of BNPP hydrolysis have been investigated. The kinetic mathematical model of BNPP cleavage catalyzed by these complexes has been proposed. The effects of reaction temperature and metal ion in the complexes on the rate of BNPP catalytic hydrolysis have been discussed. The results show that the hydroxamic acid complexes containing benzo-15-crown-5 exhibit high activity in the BNPP catalyzed hydrolysis; the pseudo-first-order-rate constants of BNPP hydrolysis catalyzed by the complexes increase along with the increases of pH of the buffer solution from 7.50 to 9.50; the activity of different metal ions decreases in the order: Co 2+ > Cu 2+ > Zn 2+ > Mn 2+ ; the pseudo-first-order-rate constants of BNPP hydrolysis catalyzed by the complexes is 2.24 · 10 5 $ 3.24 · 10 5 times as large as that of spontaneous hydrolysis of BNPP.

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Section: General Methods and Materialsmentioning

confidence: 99%

Studies on the reaction kinetics and the mechanism of hydrolysis of bis(4-nitrophenyl)phosphate (BNPP) by hydroxamic acid complexes containing benzo-15-crown-5

Zhou

et al. 2005

Transition Met Chem

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“…4¢-(x-Carboxylvaleryl)benzo-15-crown-5 (1a),4¢-(x-carboxylheptanoyl)benzo-15-crown-5 (1b), 4¢-(x-carboxyl nonanoyl)benzo-15-crown-5 (1c) [10] and N-phenylhydroxylamine [11] were synthesized according to literature methods. All other reagents were of analytical grade and were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Oxygenation and Catalytic Epoxidation Performance of Transition-metal Hydroxamate with Benzo-15-Crown-5

Qin

2006

Transition Met Chem

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A series of novel hydroxamic acid complexes (ML 1 2 $ ML 3 2 , M¼Co II , Mn III Cl) containing benzo-15-crown-5 and their analogues, ML 4 2 , were successfully synthesized starting from benzo-15-crown-5 (B15C5) or 1,2-dimethoxybenzene. Their structures were characterized by 1 H-NMR, IR, and MS as well as by elemental analysis. Moreover, the saturated oxygen uptake of their cobalt(II) complexes, CoL 1 2 -CoL 4 2 , in diethyleneglycol dimethyl ether was determined over the )5 to +20°C range. The oxygenation constants (Ko 2 ) and thermodynamic parameters (DH 0 and DS 0 ) were calculated. Meanwhile, the corresponding Mn (III) hydroxamates were employed as models of monooxygenase to catalyze PhCH¼CH 2 epoxidation at ambient temperature and pressures. The effects of pendant B15C5 and adding sodium cation on the O 2 -binding capabilities, and the catalytic oxidation performance of the complexes (ML 1 2 $ ML 3 2 ), were investigated and compared with the uncrowned analogue ML 4 2 . The results indicated that the B15C5-functionalized Co(II) complexes (CoL 1 2 $ CoL 3 2 ) showed high activity in the dioxygen affinities, and the MnL 1 2 Cl exhibited the best catalytic activity: the conversion of PhCH@CH 2 and epoxidation selectivity were up to 27.14%, 100% respectively.

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“…Tris(hydroxymethyl)aminomethane was supplied by Sigma Chemical Co. The pH value of the buffer solutions was measured at 25 The following compounds were prepared according to the literature: N-phenylhydroxylamine, 18 PNPP(p-nitrophenyl picolinate), 19 4'-(ω-chloroformylvaleryl)benzo-15-crown-5 and 4'-(ω-chloroformylheptatanoyl)benzo-15-crown-5. 20 PNPP stock solution for kinetics was prepared in acetonitrile.…”

Section: Methodsmentioning

confidence: 99%

Kinetics and Mechanism of Hydrolysis of P-Nitrophenyl Picolinate by Transition-Metal Hydroxamate Containing Benzo-15-Crown-5

Tang

Fěng

et al. 2006

Journal of Chemical Research

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Two hydroxamic acids HL 1 and HL 2 containing benzo-15-crown-5 have been synthesised and their transition metal (Cu 2+ , Co 2+ , Zn 2+ , Mn 2+ ) complexes have been employed as models to mimic hydrolase in catalytic hydrolysis of p-nitrophenyl picolinate(PNPP). The kinetics and mechanism of PNPP hydrolysis have been investigated. A kinetic mathematical model of PNPP cleavage catalysed by these complexes is proposed. The effects of reactive temperature and metal ion in complexes on the rate of catalytic PNPP hydrolysis are discussed. The results show that the transition-metal hydroxamates (ML 1 2 , ML 2 2 , M= Cu 2+ , Co 2+ , Zn 2+ , Mn 2+ ) containing benzo-15-crown-5 exhibit high activity in catalytic PNPP hydrolysis. The rate of PNPP hydrolysis catalysed by these complexes increased along with the increase of pH values of the buffer solution; the catalytic activity of different metal ions in complexes of the same ligand deceased in the order Cu 2+ > Co 2+ >Zn 2+ > Mn 2+ ; the pseudo-first-order-rate constants of PNPP hydrolysis catalysed by the complexes are over 1000 times more than that of spontaneous hydrolysis of PNPP.

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The metal-complexing properties of N-benzoyl-N-phenylhydroxylamine derivatives containing N-phenyl ring substituents

Cited by 13 publications

References 9 publications

Studies on the reaction kinetics and the mechanism of hydrolysis of bis(4-nitrophenyl)phosphate (BNPP) by hydroxamic acid complexes containing benzo-15-crown-5

Studies on the reaction kinetics and the mechanism of hydrolysis of bis(4-nitrophenyl)phosphate (BNPP) by hydroxamic acid complexes containing benzo-15-crown-5

Synthesis, Oxygenation and Catalytic Epoxidation Performance of Transition-metal Hydroxamate with Benzo-15-Crown-5

Kinetics and Mechanism of Hydrolysis of P-Nitrophenyl Picolinate by Transition-Metal Hydroxamate Containing Benzo-15-Crown-5

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