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The direct nitration of aniline with nitric acid and sulfuric acid, according to one source, [12] results in a 50/50 mixture of para- and meta-nitroaniline isomers. In this reaction the fast-reacting and activating aniline (ArNH 2 ) exists in equilibrium with the more abundant but less reactive (deactivated) anilinium ion (ArNH 3 + ), which may ...
Many other methods exist for the synthesis of this compound. Direct nitration of aniline is inefficient since anilinium is produced instead. Nitration of acetanilide gives only traces of 2-nitro isomer is obtained due to the great steric effect of the amide. Sulfonation is usually used to block the 4 position and increases the effectiveness to 56%.
The nitration of the 2 position involves the loss of CO 2 as the leaving group. Desulfonation in which a sulfonyl group is substituted by a proton is a common example. See also Hayashi rearrangement. In aromatics substituted by silicon, the silicon reacts by ipso substitution.
Aniline (from Portuguese anil 'indigo shrub', and -ine indicating a derived substance) [6] is an organic compound with the formula C 6 H 5 NH 2. Consisting of a phenyl group ( −C 6 H 5 ) attached to an amino group ( −NH 2 ), aniline is the simplest aromatic amine .
Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles. [6] It is nitrated to produce tetryl, a derivative with four nitro groups which was once used as explosive. In acidic solution, the initial nitration gives 3-nitrodimethylaniline. [7]
Nitrosation of aniline. N-Nitrosamines arise from the reaction of nitrite sources with amino compounds. Typically, this reaction occurs when the nucleophilic nitrogen of a secondary amine attacks the nitrogen of the electrophilic nitrosonium ion: [14] NO 2 − + 2 H + → NO + + H 2 O R 2 NH + NO + → R 2 N-NO + H +
The term nitroaniline in chemistry refers to a derivative of aniline (C 6 H 5 NH 2) containing a nitro group (—NO 2) There are three simple nitroanilines of formula C 6 H 4 (NH 2)(NO 2) which differ only in the position of the nitro group: 2-Nitroaniline; 3-Nitroaniline; 4-Nitroaniline
The inductive and resonance properties compete with each other but the resonance effect dominates for purposes of directing the sites of reactivity. For nitration, for example, fluorine directs strongly to the para position because the ortho position is inductively deactivated (86% para, 13% ortho, 0.6% meta).