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Concept
Aniline
Summary
Aniline (, and -ine indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
Relative to benzene, it is electron-rich. It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone to oxidation: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the formation of strongly colored, oxidized impurities. Aniline can be diazotized to give a diazonium salt, which can then undergo various nucleophilic substitution reactions.
Like other amines, aniline is both a base (pKaH = 4.6) and a nucleophile, although less so than structurally similar aliphatic amines.
Because an early source of the benzene from which they are derived was coal tar, aniline dyes are also called coal tar dyes.
In aniline, the C−N bond length is 1.41 Å, compared to the C−N bond length of 1.47 Å for cyclohexylamine, indicating partial π-bonding between C(aryl) and N. The length of the chemical bond of in anilines is highly sensitive to substituent effects. The C−N bond length is 1.34 Å in 2,4,6-trinitroaniline vs 1.44 Å in 3-methylaniline.
The amine group in anilines is a slightly pyramidalized molecule, with hybridization of the nitrogen somewhere between sp3 and sp2. The nitrogen is described as having high p character. The amino group in aniline is flatter (i.e., it is a "shallower pyramid") than that in an aliphatic amine, owing to conjugation of the lone pair with the aryl substituent.
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