Carbazolyl nitrenium ion: Electron configuration and antiaromaticity assessed by laser flash photolysis, trapping rate constants, product analysis, and computational …

AH Winter, HH Gibson, DE Falvey

Index: Winter, Arthur H.; Gibson, Harry H.; Falvey, Daniel E. Journal of Organic Chemistry, 2007 , vol. 72, # 22 p. 8186 - 8195

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Citation Number: 9

Abstract

Laser flash photolysis of 1-(carbazol-9-yl)-2, 4, 6-trimethylpyridinium tetrafluoroborate generates the carbazolyl nitrenium ion (τ= 333 ns, k obs= 3.0× 106 M-1s-1) having absorption bands at 570 and 620 nm in CH3CN. The nitrenium ion is found to have reactivity comparable to structurally similar closed-shell diarylnitrenium ions, but spectroscopic evidence favors an open-shell singlet diradical assignment for the observed nitrenium ion. ...