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• W2078233635 endingPage "4634" @default.
• W2078233635 startingPage "4626" @default.
• W2078233635 abstract "The reactive intermediates N,N-di(4-chlorophenyl)nitrenium ion and N,N-di(4-bromophenyl)nitrenium ion were generated through photolysis of the corresponding N-amino(2,4,6,-collidinium) ions. The behavior of these diarylnitrenium ions was characterized by laser flash photolysis, analysis of the stable photoproducts, and ab initio calculations with density functional theory. The latter predict these species to have singlet ground states. The halogenated diarylnitrenium ions are significantly longer lived than the unsubstituted diphenylnitrenium ion. Specifically, cyclization to form carbazole derivatives occurs negligibly, if at all, with the halogenated derivatives. They do, however, carry out most of the characteristic reactions of singlet arylnitrenium ions, including combining with nucleophiles on the aryl rings, adding to arenes, and accepting electrons from readily oxidized traps. Interestingly these species also abstract H atoms from 1,4-cyclohexadiene and various phenol derivatives. The implication of the latter process in relation to the computed singlet-triplet energy gaps of ca. -12.5 kcal/mol is discussed." @default.
• W2078233635 created "2016-06-24" @default.
• W2078233635 creator A5087548276 @default.
• W2078233635 creator A5091872913 @default.
• W2078233635 date "2007-05-31" @default.
• W2078233635 modified "2023-10-18" @default.
• W2078233635 title "<i>N</i>,<i>N</i>-Di(4-halophenyl)nitrenium Ions: Nucleophilic Trapping, Aromatic Substitution, and Hydrogen Atom Transfer" @default.
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• W2078233635 doi "https://doi.org/10.1021/jo062578i" @default.
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