1-Methyl-4-ethynylpridinum triflate: Reaction with thiophenol giving rise to chromophoric (E)-1-methyl-4-[2-(phenylsulfanyl)-1-ethenyl]pyridinium triflate. An example of nucleophilic reaction on triple bond. | [Journal of Chemical Society of Pakistan • 2012]

Author(s):

1. Ramazan Erenler: Institute of Chemistry, Academia Sinica, Nankang 115, Taipei, Taiwan;Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University 60240 Tokat-Turkey

2. Jean-François Biellmann: National Central University Jhongli Taiwan

Abstract:

1-Methyl-4-ethynylpridinum triflate 6 was prepared by treatment of 4-ethynylpyridine 5 with methyl triflate in dichloromethane. Thiophenol added to the triple bond to give regioselectively (E)-1-methyl-4-[2-(phenylsulfanyl)-1-ethenyl]pyridinium triflate 7. The addition of glutathione to 1-methyl-4-ethynylpridinum triflate 6 with in TES buffer at pH 7 was a second order reaction (k=4200 M-1 s-1 at 25°C). The addition products showed an intense long wavelength absorption band (λmax=360 nm, ε=27500 M-1 cm-1). The reaction rate and the spectroscopic properties show the usefulness of 4-ethynyl-1-methylpridinium triflate 6 as reagent for the determination of thiol.

Page(s): 1224-1228

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 34, Issue: 5, Year: 2012

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