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Aniline and its ring-substituted derivatives react with nitrous acid to form diazonium salts. One example is benzenediazonium tetrafluoroborate. Through these intermediates, the amine group can be converted to a hydroxyl (−OH), cyanide (−CN), or halide group (−X, where X is a halogen) via Sandmeyer reactions.
A white solid, it is the chloride salt of anilinium, which is the conjugate acid of aniline, C 6 H 5 NH 2. Anilinium chloride is produced by treatment of aniline with hydrochloric acid. The cation consists of a phenyl ring attached to a tetrahedral ammonium center. The C-N bond elongates from 1.41 Å in aniline to 1.474 Å in anilinium. [2]
Aniline is a benzenoid compound. The NH 2 group attached to the benzene ring means that there is a lone pair of electrons that can enter into conjugation with the benzene ring resulting in delocalization in the aniline. Aniline absorbs in the K (220 - 250 nm) and the B (250 - 290 nm) bands exhibited by benzenoid compounds.
For example, the Kamlet-Taft parameters are dipolarity/polarizability (π*), hydrogen-bonding acidity (α) and hydrogen-bonding basicity (β). These can be calculated from the wavelength shifts of 3–6 different solvatochromic dyes in the solvent, usually including Reichardt's dye , nitroaniline and diethylnitroaniline .
An example is Disperse Orange 1. Some azo compounds, e.g., methyl orange, are used as acid-base indicators. Most DVD-R/+R and some CD-R discs use blue azo dye as the recording layer. Many phenolic diazo dyes participate in tautomeric equilibria shown here in simplified form (Ar = aryl). [6] Azo dyes are solids.
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