4-Iodobenzoic acid, or ''p''-iodobenzoic acid, is an isomer of iodobenzoic acid.

Structure

X-ray crystallography X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...

of 4-iodobenzoic acid has shown that it crystallizes in the solid state as hydrogen-bonded dimers which

stack Stack may refer to: Places * Stack Island, an island game reserve in Bass Strait, south-eastern Australia, in Tasmania’s Hunter Island Group * Blue Stack Mountains, in Co. Donegal, Ireland People * Stack (surname) (including a list of people ...

perpendicular to their aromatic rings. The iodine atoms of adjacent dimers are also oriented towards each other due to

van der Waals forces In molecular physics and chemistry, the van der Waals force (sometimes van der Waals' force) is a distance-dependent interaction between atoms or molecules. Unlike ionic or covalent bonds, these attractions do not result from a chemical ele ...

Preparation

4-Iodobenzoic acid may be prepared in the laboratory by the oxidation of ''p''-iodotoluene with

potassium permanganate Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, which dissolves in water as K+ and ions to give an intensely pink to purple solution. Potassium permanganate is widely us ...

Reactions

The carboxylic acid functionality of 4-iodobenzoic acid undergoes

Fischer–Speier esterification Fischer esterification or Fischer–Speier esterification is a special type of esterification by refluxing a carboxylic acid and an Alcohol (chemistry), alcohol in the presence of an acid catalyst. The reaction was first described by Emil Fischer ...

with

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

to form the ester methyl 4-iodobenzoate.

References

{{DEFAULTSORT:Iodobenzoic acid, 4- Benzoic acids 4-Iodophenyl compounds