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

Yingjin Liu, Naoto Horiuchi, Yoshimi Sueishi, Shunzo Yamamoto

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The kinetics of the hydride transfer reaction between Methylene Blue (MB+) and 1-benzyl-1,4-dihydronicotinamide (BNAH) were studied in 10% ethanol-90% water mixed solvents containing β- and γ-cyclodextrins (β-CD and γ-CD). The pseudo-first order rate constant shows kinetic saturation at high initial concentration of BNAH. This indicates the formation of a complex between MB+ and BNAH. The reaction was suppressed by addition of β-CD, but enhanced by addition of γ-CD. MB+ and BNAH were separately accommodated within the β-CD cavity and the cavity walls may protect the activity site of the reactants. On the other hand, in the MB+-BNAH-γ-CD system, the inclusion of the complex between MB+ and BNAH with γ-CD occurred. This effect of γ-CD can distinguish between the productive and non-productive nature of the complex.

Original languageEnglish
Pages (from-to)233-239
Number of pages7
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume54
Issue number3-4
DOIs
Publication statusPublished - Apr 2006

Fingerprint

hydrides
cyclodextrins
methylene blue
Methylene Blue
Cyclodextrins
Hydrides
kinetics
cavities
Kinetics
Rate constants
ethyl alcohol
Ethanol
ethanol
inclusions
saturation
Water
water
1-benzyl-1,4-dihydronicotinamide

Keywords

  • 1-benzyl-1,4-dihydronicotinamide
  • Cyclodextrin
  • Hydride transfer reaction
  • Inclusion complexes
  • Methylene blue
  • Reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

Cite this

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title = "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",
abstract = "The kinetics of the hydride transfer reaction between Methylene Blue (MB+) and 1-benzyl-1,4-dihydronicotinamide (BNAH) were studied in 10{\%} ethanol-90{\%} water mixed solvents containing β- and γ-cyclodextrins (β-CD and γ-CD). The pseudo-first order rate constant shows kinetic saturation at high initial concentration of BNAH. This indicates the formation of a complex between MB+ and BNAH. The reaction was suppressed by addition of β-CD, but enhanced by addition of γ-CD. MB+ and BNAH were separately accommodated within the β-CD cavity and the cavity walls may protect the activity site of the reactants. On the other hand, in the MB+-BNAH-γ-CD system, the inclusion of the complex between MB+ and BNAH with γ-CD occurred. This effect of γ-CD can distinguish between the productive and non-productive nature of the complex.",
keywords = "1-benzyl-1,4-dihydronicotinamide, Cyclodextrin, Hydride transfer reaction, Inclusion complexes, Methylene blue, Reaction mechanism",
author = "Yingjin Liu and Naoto Horiuchi and Yoshimi Sueishi and Shunzo Yamamoto",
year = "2006",
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T1 - 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

AU - Liu, Yingjin

AU - Horiuchi, Naoto

AU - Sueishi, Yoshimi

AU - Yamamoto, Shunzo

PY - 2006/4

Y1 - 2006/4

N2 - The kinetics of the hydride transfer reaction between Methylene Blue (MB+) and 1-benzyl-1,4-dihydronicotinamide (BNAH) were studied in 10% ethanol-90% water mixed solvents containing β- and γ-cyclodextrins (β-CD and γ-CD). The pseudo-first order rate constant shows kinetic saturation at high initial concentration of BNAH. This indicates the formation of a complex between MB+ and BNAH. The reaction was suppressed by addition of β-CD, but enhanced by addition of γ-CD. MB+ and BNAH were separately accommodated within the β-CD cavity and the cavity walls may protect the activity site of the reactants. On the other hand, in the MB+-BNAH-γ-CD system, the inclusion of the complex between MB+ and BNAH with γ-CD occurred. This effect of γ-CD can distinguish between the productive and non-productive nature of the complex.

AB - The kinetics of the hydride transfer reaction between Methylene Blue (MB+) and 1-benzyl-1,4-dihydronicotinamide (BNAH) were studied in 10% ethanol-90% water mixed solvents containing β- and γ-cyclodextrins (β-CD and γ-CD). The pseudo-first order rate constant shows kinetic saturation at high initial concentration of BNAH. This indicates the formation of a complex between MB+ and BNAH. The reaction was suppressed by addition of β-CD, but enhanced by addition of γ-CD. MB+ and BNAH were separately accommodated within the β-CD cavity and the cavity walls may protect the activity site of the reactants. On the other hand, in the MB+-BNAH-γ-CD system, the inclusion of the complex between MB+ and BNAH with γ-CD occurred. This effect of γ-CD can distinguish between the productive and non-productive nature of the complex.

KW - 1-benzyl-1,4-dihydronicotinamide

KW - Cyclodextrin

KW - Hydride transfer reaction

KW - Inclusion complexes

KW - Methylene blue

KW - Reaction mechanism

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