Year-end Sale % OFF 
Abstract
To get more insight into the reactions of nitrosoarenes with thiols which may be responsible for cytotoxic effects, the reaction mechanism was studied with nitrosobenzene and 1-thioglycerol as model compounds. A transient intermediate was isolated by high performance liquid chromatography and identified as 2,3-dihydroxypropanesulfenic N-hydroxyphenylamide ("semimercaptal") by UV, 13C-NMR, and FAB mass spectroscopy. In aqueous solution this labile compound reassembles into 2,3-dihydroxypropanesulfinic phenylamide in a first order reaction. In the presence of excess thiol or ascorbic acid the "semimercaptal" is reduced to 2,3-dihydroxypropanesulfenic phenylamide without transient formation of a complete "mercaptal". Hydrolysis rather than thiolysis liberates aniline from the sulfenic phenylamide. Both the sulfinic and sulfenic phenylamides were obtained in crystalline form and identified by NMR and FAB mass spectroscopy. A scheme is presented of the known reactions of nitrosoarenes with thiols.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
