Abstract
N-Nitrosuccinimide (S-NO2) engages in weak charge transfer complexes with aromatic compounds (ArH). Upon photolysis with light of λ > 345 nm in dichloromethane, electron transfer within the charge transfer complex leads to the triad [ArH˙+ S– NO2] from which products of eventual Succinimidylation and/or nitration develop by initial attack of succinimide anion upon the radical cation. Photolysis in the presence of trifluoroacetic acid (0.4 mol dm–3) causes inactivation of S– by protonation, making EPR detection of ArH˙+ or radical cations formed by its further transformations possible. In acetonitrile, trifluoroacetic acid is too weak effectively to protonate S–, whereas addition of stronger acids again leads to the development of EPR spectra of ArH˙+ in the case of 9,10-dimethylanthracene, the intensity increasing with decreasing pK of the acid.An X-ray crystal structure is reported for N-nitrosuccinimide.
Sign-in/Register to access full text options 
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 callMore From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: 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.
