Elucidation of the Role of the Complex in Hydride Transfer Reaction between Methylene Blue and 1-Benzyl-1,4-dihydronictinamide by Effect of γ-Cyclodextrin

Liu, Yingjin; Horiuchi, Naoto; Sueishi, Yoshimi; Yamamoto, Shunzo

doi:10.1007/s10847-005-8119-5

Cited by 3 publications

(1 citation statement)

References 30 publications

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“…There are many reports on photoionization behavior of phenothiazines in different organic and micellar solutions. − Another area of growing application of phenothiazine and phenoxazine compounds is as light-emitting and charge-transport materials in solid-state organic electronic devices, such as light-emitting diodes, thin-film transistors, and photovoltaic cells . The salts of phenothiazines are also immensely important compounds and are extensively employed in dye industry and medical chemistry. − As a typical example, methylene blue (MB + ) not only is an important member of the thiazine dye family but also can be used as photosensitizer to produce singlet oxygen in photodynamic therapy for the treatment of cancer. − The neutral and charged radicals of phenothiazines as important reaction intermediates of phenothiazines not only are quite stable but also have many special chemical properties and important roles which are evidently different from their corresponding parent compounds. − Because of having many important roles in medicine, bioantioxidation and dye, phenothiazines and their various reaction intermediates have been very interesting chemical species in medicinal chemistry, antioxidant chemistry, and dye chemistry. Many famous chemists have devoted most of their time to the study on the chemistry of phenothiazines.…”

Section: Introductionmentioning

confidence: 99%

Driving Forces for the Mutual Conversions between Phenothiazines and Their Various Reaction Intermediates in Acetonitrile

Zhu

Dai

et al. 2008

J. Phys. Chem. B

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The thermodynamic driving forces (defined as the enthalpy changes or redox potentials in this work) of the 18 phenothiazines and their analogues, phenoxazine, N-methyl-dihydrophenazine, 9H-thioxanthene, 9H-xanthene and 9,10-dihydro- N-methylacridine, to release hydride, hydrogen atom, proton, and electron in acetonitrile, the thermodynamic driving forces of the radical cations of the phenothiazines and the analogues to release hydrogen atom, proton, and electron in acetonitrile, and the thermodynamic driving forces of the cations of the phenothiazines with two positive charges and their analogues to release proton in acetonitrile were estimated by using experimental methods. The effect of the remote substituents on the 11 determined thermodynamic driving forces were examined according to Brown's substituent parameters; the results show that the values of the 11 thermodynamic driving forces all are linearly dependent on the sum of Brown substituent parameters (sigma +) with very good correlation coefficients, which indicates that for any one- or multisubstituted at para- and/or meta-position phenothiazines and their various reaction intermediates, the 11 thermodynamic driving forces all can be easily and safely estimated from the corresponding Brown substituent parameters (sigma +). The relative effective charges on the center nitrogen atom in phenothiazines and their various reaction intermediates were estimated from the related Hammett-type linear free-energy relationships, which can be used to efficiently measure the electrophilicity, nucleophilicity, and dimerizing ability of the corresponding reaction intermediates of phenothiazines and their analogues. All the information disclosed in this work could not only supply a gap of the chemical thermodynamics on the mutual conversions between phenothiazines and their various reaction intermediates in solution but also strongly promote the fast development of the chemistry and application of phenothiazines and their analogues.

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Section: Introductionmentioning

confidence: 99%

Driving Forces for the Mutual Conversions between Phenothiazines and Their Various Reaction Intermediates in Acetonitrile

Zhu

Dai

et al. 2008

J. Phys. Chem. B

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Effects of Ionic Surfactants and Cyclodextrins on Hydride-Transfer Reaction of 1-Benzyl-1,4-dihydronicotinamide with Methylene Blue

Matsumoto

Liu

Sueishi³

et al. 2007

Bulletin of the Chemical Society of Japan

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The kinetics of the hydride-transfer reaction between methylene blue (MB+) and 1-benzyl-1,4-dihydronictinamide (BNAH) were studied in media containing cyclodextrins (β- and γ-CD) and surfactants (sodium dodecyl sulfate (SDS), dodecyltrimethylammonium bromide, tetradecyltrimethylammonium bromide, and hexadecyltrimethylammonium bromide). Cationic surfactants decreased the apparent first-order rate constant (kobsd) above the cmc, while SDS increased kobsd just above the cmc and then decreased kobsd with increasing surfactant concentration. This behavior for cationic surfactants was typical of micellar effects due to a separation of the reactants by the micelles. BNAH associated with micelles, whereas MB+ ions were repelled from the cationic interface of the micelles. Binding of BNAH and MB+ to the same SDS micelle enhanced the reaction, but dilution of reagents within the micellar interface with the increase in [SDS] caused a decrease in kobsd. In β-CD–cationic surfactant mixtures, the results were interpreted in terms of the model which takes into account the formation of CD–BNAH, CD–MB+, and CD–surfactant complexes and the association of BNAH with micelles. The decrease in kobsd with increasing surfactant concentration observed in γ-CD–cationic surfactant mixtures can be explained by the decrease in the concentration of free γ-CD by the formation of 1:1 and 2:1 complexes of surfactant monomer with γ-CD.

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Effects of Anionic Surfactants on the Hydride-Transfer Reaction of NADH with Methylene Blue: In Premicellar and Micellar Regions

Matsumoto

Otsuki

Sueishi³

et al. 2008

Bulletin of the Chemical Society of Japan

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The kinetics of the hydride-transfer reaction between methylene blue (MB) and reduced nicotinamide–adenine dinucleotide (NADH) were studied in basic buffer solutions containing anionic surfactants (sodium dodecyl sulfate (SDS), sodium decyl sulfate (SDES), and sodium tetradecyl sulfate (STS)) under oxygen-saturated conditions. Initially, the absorbance of MB at 666 nm decreased with SDES concentration, but increased gradually near and above the cmc. The observed first-order rate constant (kobsd) decreased gradually at first, more steeply with increasing SDES concentration and then reached to a small value and became constant. The changes in the absorbance of MB and the observed rate constant were explained by changes in the form of MB in the solution with increasing SDES concentration. The concentration of SDES can be divided into four regions, in connection with the changes in the absorbance and the observed rate constant. The profiles of the changes in the absorbance of MB and the apparent rate constant for SDS and STS with surfactant concentrations were very similar to those for SDES.

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Elucidation of the Role of the Complex in Hydride Transfer Reaction between Methylene Blue and 1-Benzyl-1,4-dihydronictinamide by Effect of γ-Cyclodextrin

Cited by 3 publications

References 30 publications

Driving Forces for the Mutual Conversions between Phenothiazines and Their Various Reaction Intermediates in Acetonitrile

Driving Forces for the Mutual Conversions between Phenothiazines and Their Various Reaction Intermediates in Acetonitrile

Effects of Ionic Surfactants and Cyclodextrins on Hydride-Transfer Reaction of 1-Benzyl-1,4-dihydronicotinamide with Methylene Blue

Effects of Anionic Surfactants on the Hydride-Transfer Reaction of NADH with Methylene Blue: In Premicellar and Micellar Regions

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