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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.
The tables below provides information on the variation of solubility of different substances (mostly inorganic compounds) in water with temperature, at one atmosphere pressure. Units of solubility are given in grams of substance per 100 millilitres of water (g/(100 mL)), unless shown otherwise.
For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, H 2 NC 6 H 4 SO 3 H. If bromine water is added to aniline, the bromine water is decolourised and a white precipitate of 2,4,6-tribromoaniline is formed. To generate the mono-substituted product, a protection with acetyl chloride is required:
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]
The following chart shows the solubility of various ionic compounds in water at 1 atm pressure and room temperature (approx. 25 °C, 298.15 K). "Soluble" means the ionic compound doesn't precipitate, while "slightly soluble" and "insoluble" mean that a solid will precipitate; "slightly soluble" compounds like calcium sulfate may require heat to precipitate.
In the industrial production, MDA is produced by reaction of formaldehyde and aniline in the presence of hydrochloric acid. [3] MDA is a common monomer in the synthesis of polymer materials. These include polyamides, [4] polyimides and polyimines. [5] MDA is also used extensively as a precursor to methylene diphenyl diisocyanate (MDI).
4-Bromoaniline is a compound where an aniline molecule is substituted with a bromine atom on the para position. Commercially available, this compound may be used as a building block, e.g. in the preparation of monobrominated biphenyl via the Gomberg-Bachmann reaction .
A comparison of S N 1 to S N 2 reactions is to the right. On the left is an S N 1 reaction coordinate diagram. Note the decrease in ΔG ‡ activation for the polar-solvent reaction conditions. This arises from the fact that polar solvents stabilize the formation of the carbocation intermediate to a greater extent than the non-polar-solvent ...