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Kinetic Evidence for the Coexistence of Zwitterionic, Neutral and Anionic Intermediates during Rearrangement of S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiuronium Bromide to 5-(2-Hydroxyethyl)-2-(4-methoxyphenylimino)-1,3-thiazolidin-4-one
Authors: Váňa Jiří | Sedlák Miloš | Hanusek Jiří
Year: 2010
Type of publication: článek v odborném periodiku
Name of source: Journal of Organic Chemistry
Publisher name: American Chemical Society
Place: Washington
Page from-to: 3729-3736
Titles:
Language Name Abstract Keywords
cze Kinetický důkaz koexistence obojetného, neutrálního a anionického intermediátu během přesmyku S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyfenyl)isothiouronium bromidu na 5-(2-Hydroxyethyl)-2-(4-methoxyfenylimino)-1,3-thiazolidin-4-on za podmínek pseudoprvního řádu a při 25C byla v pufrech a vodné HCl studována kinetika a mechanismus přesmyku S-(2-oxotetrahydrofuran-3-yl)-N-(4-methoxyfenyl)isothiouronium bromidu na 5-(2-hydroxyethyl)-2-[(4-methoxyfenyl)imino]-1,3-thiazolidin-4-on. Několik zlomů v pH profilu potvrzuje tvorbu tří různých, kineticky detekovatelných intermediátů T+/-, T0 and T-. Jejich koexistence je velmi vzácná a je možná díky relativně zvýšené stabilitě těchto intermediátů, jejichž rozpad na produkty vyžaduje účast kyseliny. Kinetika; obojetný intermediát; neutrální intermediát; anionický intermediát; přesmyk; S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyfenyl)isothiouronium bromid; 5-(2-hydroxyethyl)-2-(4-methoxyfenylimino)-1,3-thiazolidin-4-on
eng Kinetic Evidence for the Coexistence of Zwitterionic, Neutral and Anionic Intermediates during Rearrangement of S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiuronium Bromide to 5-(2-Hydroxyethyl)-2-(4-methoxyphenylimino)-1,3-thiazolidin-4-one The kinetics and mechanism of rearrangement of S-(2-oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiuronium bromide into 5-(2-hydroxyethyl)-2-[(4-methoxyphenyl)imino]-1,3-thiazolidin-4-one have been studied under pseudo-first-order reaction conditions in aqueous buffer solutions and in diluted HCl at 25 degrees C. Multiple breaks in the pH profile establish the formation of three different kinetically detectable intermediates T+/-, T-0 and T-. Coexistence of all three kinetically detectable intermediates is very rare and is possibly due to relatively enhanced stability of these intermediates necessitating participation of an acid for progression to products. Kinetics; Zwitterionic intermediate; Neutral intermediate; Anionic intermediate; Rearrangement; S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiuronium Bromide; 5-(2-Hydroxyethyl)-2-(4-methoxyphenylimino)-1,3-thiazolidin-4-one

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