By D.L.H. Williams
On the grounds that 1988, there was a lot literature released at the chemistry of nitric oxide, quite within the box of S-nitrosation and the chemistry of S-nitroso compounds. Written through a chemist for the chemistry neighborhood, this booklet presents an replace of the chemistry of nitrosation reactions, facing either the unreal and mechanistic elements of those reactions. It additionally appears on the chemistry of nitric oxide with regards to the superb organic homes of this straightforward diatomic molecule, which have been unknown until eventually round 1990. * offers an replace on formerly released literature on nitric oxide chemistry* comprises chapters on reagents for nitrosation, nitrosation at nitrogen, aliphatic and fragrant carbon, oxygen, sulfur and steel centres* seems at scorching learn subject matters similar to synthesis, homes and reactions of s-nitrosothiols
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Extra resources for Nitrosation Reactions and the Chemistry of Nitric Oxide
Example text
The nitrosation reaction can also yield a nitrosamine derived from reaction at the secondary amine group, but this is generally a minor pathway. Reaction can be effected using the usual nitrosating agents, including the use of nitrogen oxides in the gas phase. The reaction has been used with proteins in the classical Van Slyke procedure to determine the number of primary amine groups present. g. nitrosamines from proline and tryptophan derivatives and a disulfide from a cysteine residue, presumably by S-nitrosation and subsequent decomposition.
5. Amides and related compounds Amides generally react more slowly in nitrosation than do amines, no doubt due to the presence of the strongly electron-withdrawing carbonyl group. Nitrous acid in aqueous acid solution has proved not to be such a good reagent for amides. Primary amides result in the deamination products (the carboxylic acid and nitrogen), Eq. (113), using either alkyl nitrites in organic solvents [185] or nitrosonium salts such as the tetrafluoroborate in acetonitrile [186]. RCONH2 ^^^^» or NO RCO2H + N2 (113) Similarly secondary amides react to give nitrosamides.
A similar pattern was observed for the reaction of nitrosyl chloride with amines in non-acidic aqueous solution using a competition method to get the rate constants for CINO attack relative to that of CINO hydrolysis (to N02~ and C r ) . The product ratios [RN2"^]/[N02~] give the relative rate constants, which tend to level off for amines where the pX^ values are > --3 [40], as shown in Figure 3. e. at low acidity), to change the rate limiting step to that of the formation of XNO. This has been achieved for aniline itself for both bromide and iodide ion-catalysed reactions [156].
