Reaction of Leucomalachite Green with Chloranil

Nishimura, Norio; Motoyama, Takushi

doi:10.1246/bcsj.58.3639

Bulletin of the Chemical Society of Japan

1985

DOI: 10.1246/bcsj.58.3639

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Reaction of Leucomalachite Green with Chloranil

Norio Nishimura¹,

Takushi Motoyama²

Abstract: The reaction of Leucomalachite Green with chloranil to produce Malachite Green cations has been carried out in acetonitrile. Prior to the formation of the cations, a 1:1 CT complex is formed between the reactants. The equilibrium and the rate constants were estimated.

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1988

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Cited by 3 publications

References 3 publications

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Hydride transfer reactions of Michler's hydride with different π‐accetors

Zaman

Nishimura

Yamamoto

et al. 1994

J of Physical Organic Chem

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The hydride transfer reactions of 4,4′‐bis(dimethylaminophenyl)methane (Michler's hydride) with p‐benzoquinones were studied. The rate of formation of Michler's Hydrol Blue was followed spectrophotometrically. The second‐order rate constants and the activation parameters were estimated. The formation of a charge‐transfer complex was observed at low temperatures. Stable and unstable paramagnetic species formed during the reactions were assigned by ESR spectroscopy. The observed kinetic behaviour and the stoichiometry were in line with those previously obtained for the systems involving Leuco Crystal Violet, Leuco Malachite Green and Leuco Bindschedler's Green. Hence the reaction is considered to proceed according to the so‐far accepted multi‐step mechanism. However, when tetracyano‐p‐quinodimethane or tetracyanoethylene was used as a π‐acceptor, a comparatively stable radical ion pair was formed as a result of a one‐electron transfer, followed by the gradual formation of Michler's Hydrol Blue. The kinetic behaviour and the stoichiometry of the reaction were examined, together with the enhanced kinetic effects of added triethylamine. A modified mechanism for these systems is proposed. The role of cyanomethylenes was found to be essentially different from that of p‐benzoquinones, and therefore π‐acceptors are divided into two groups of cyanomethylenes and p‐benzoquinones.

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Hydride transfer reactions of Michler's hydride with different π‐accetors

Zaman

Nishimura

Yamamoto

et al. 1994

J of Physical Organic Chem

Self Cite

View full text Add to dashboard Cite

show abstract

Reactions of Leuco Bindschedler’s Green with Some p-Benzoquinones in Acetone

Osawa¹,

Nishimura²,

Yamamoto³

1991

Bulletin of the Chemical Society of Japan

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The rate of reaction between Leuco Bindschedler’s Green (BGH) and some p-benzoquinone derivatives (Q’s) in acetone was followed spectrophotometrically by means of the stopped-flow technique. The reaction was found to proceed reversibly. The rate data and the activation parameters for the forward and backward reactions were estimated. The rates were susceptible to the oxidation–reduction potentials of the Q’s. The absorption spectra observed at low temperatures indicated that three kinds of intermediates were involved. Radicals formed during the reaction were detected by the ESR method. The results have been discussed in relation to those previously obtained for systems involving Leuco Crystal Violet (LCV) and Leuco Malachite Green (LMG).

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New Type of Charge-Transfer Complexes between Benzoic Acid 2-[(3,5-Dibromo-4-hydroxyphenyl)-3,5-dibromo-4-oxo-2,5-cyclohexadiene-1-ylidene)methyl]-ethyl Ester (TBPE) and Aliphatic Amines

Nishimura¹,

Masaki²,

Miyake³

et al. 1988

Chemistry Letters

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Reaction of Leucomalachite Green with Chloranil

Abstract: The reaction of Leucomalachite Green with chloranil to produce Malachite Green cations has been carried out in acetonitrile. Prior to the formation of the cations, a 1:1 CT complex is formed between the reactants. The equilibrium and the rate constants were estimated.

Cited by 3 publications

References 3 publications

Hydride transfer reactions of Michler's hydride with different π‐accetors

Hydride transfer reactions of Michler's hydride with different π‐accetors

Reactions of Leuco Bindschedler’s Green with Some p-Benzoquinones in Acetone

New Type of Charge-Transfer Complexes between Benzoic Acid 2-[(3,5-Dibromo-4-hydroxyphenyl)-3,5-dibromo-4-oxo-2,5-cyclohexadiene-1-ylidene)methyl]-ethyl Ester (TBPE) and Aliphatic Amines

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