Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Carbon–Nitrogen and Nitrogen–Nitrogen Bond Formation from Nucleophilic Attack at Coordinated Nitrosyls in Fe and Ru Heme Models

Carbon–Nitrogen and Nitrogen–Nitrogen Bond Formation from Nucleophilic Attack at Coordinated Nitrosyls in Fe and Ru Heme Models
George B. Richter-Addo, Douglas R. Powell, Erwin G. Abucayon
The conversion of inorganic NOx species to organo-N compounds is an important component of the global N-cycle. Reaction of a C-based nucleophile, namely the phenyl anion, with the ferric heme nitrosyl [(OEP)Fe(NO)(5-MeIm)]+ generates a mixture of the C-nitroso derivative (OEP)Fe(PhNO)(5-MeIm) and (OEP)Fe(Ph). The related reaction with [(OEP)Ru(NO)(5-MeIm)]+ generates the (OEP)Ru(PhNO)(5-MeIm) product. Reactions with the N-based nucleophile diethylamide results in the formation of free diethylnitrosamine, whereas the reaction with azide results in N2O formation; these products derive from attack of the nucleophiles on the bound NO groups. These results provide the first demonstrations of C–N and N–N bond formation from attack of C-based and N-based nucleophiles on synthetic ferric-NO hemes.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05209

DOI: 10.1021/jacs.7b05209

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