Nitrosation Reactions and the Chemistry of Nitric Oxide by D.L.H. Williams

By D.L.H. Williams

Considering that 1988, there was a lot literature released at the chemistry of nitric oxide, really within the box of S-nitrosation and the chemistry of S-nitroso compounds. Written by means of a chemist for the chemistry group, this e-book offers an replace of the chemistry of nitrosation reactions, facing either the unreal and mechanistic elements of those reactions. It additionally seems on the chemistry of nitric oxide relating to the superb organic houses of this easy diatomic molecule, which have been unknown till round 1990. * presents an replace on formerly released literature on nitric oxide chemistry* includes chapters on reagents for nitrosation, nitrosation at nitrogen, aliphatic and fragrant carbon, oxygen, sulfur and steel centres* seems at sizzling learn issues resembling synthesis, homes and reactions of s-nitrosothiols

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The argument in the case of these nitrosation reactions is based upon the nature of Bronsted RCONHR' + XNO -5==^ Y (117) -H* ? NO RC—N^ ___ 0-% plots relating to base catalysis and the use of Eigen theory. The interpretation seems quite general for nitrosation of amides, ureas, guanidines etc. and there are a number of reports in the literature with similar experimental results notably the absence of nucleophilic catalysis. One interesting result refers to the change in rate-limiting step as the solvent composition is changed.

The dependence of the rate constant on the acidity suggested that reaction occurred (unusually) with the protonated form of the aniline. S-Nitrosation of a cysteine residue in proteins by N-methyl-Nnitrosoaniline has also been reported [137], although it is not known if this is a direct reaction. Nitrosation by nitrosamines can also be brought about in non-aqueous solvents. Thus indoles undergo C-nitrosation, Eq. (86), when treated with Nnitrosodiphenylamine in a mixture of chloroform and trichloroacetic acid as solvent [138].

The indirect nature of the transfer can be demonstrated by interception of the nitrous acid generated by denitrosation, by a substrate more reactive than the amine [133]. 32 Nitrosation Reactions and the Chemistry of Nitric Oxide The denitrosation reaction has been used to generate 4-nitrosophenol which condenses with a second phenol molecule to give a quinone-imine which is coloured bright red in acid solution and blue in alkaline solution, Eq. (84). This is the chemistry behind the Liebermann qualitative test for a nitrosamine \ H30'^ f^NO ^ \ NH + HNO2 phenol ^ Of^ ^^—\ V-OH (84) phenol Blue Red [134], or an alkyl nitrite.

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Nitrosation Reactions and the Chemistry of Nitric Oxide by D.L.H. Williams
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