4-Iodobenzoic acid explained

4-Iodobenzoic acid, or p-iodobenzoic acid, is an isomer of iodobenzoic acid.^[1]

Structure

X-ray crystallography of 4-iodobenzoic acid has shown that it crystallizes in the solid state as hydrogen-bonded dimers which stack perpendicular to their aromatic rings. The iodine atoms of adjacent dimers are also oriented towards each other due to van der Waals forces.^[2]

Preparation

4-Iodobenzoic acid may be prepared in the laboratory by the oxidation of p-iodotoluene with potassium permanganate.^[3]

Reactions

The carboxylic acid functionality of 4-iodobenzoic acid undergoes Fischer–Speier esterification with methanol to form the ester methyl 4-iodobenzoate.^[4]

Notes and References

1. Web site: 4-Iodobenzoic acid . 2023-01-21 . . en.
2. Nygren . Cara L. . Wilson . Chick C. . Turner . John F. C. . 2005 . On the Solid State Structure of 4-Iodobenzoic Acid . . 109 . 11 . 2586–2593 . 10.1021/jp047189b. 16833563 . 2005JPCA..109.2586N .
3. Varma . P. S. . Panickerp . P. B. . 1928 . Influence of substitution on the oxidation of side chains in the benzene nucleus . Proc. 15th Indian Sci. Cong..
4. Gadzikwa . Tendai . Zeng . Bi-Shun . Hupp . Joseph T. . Nguyen . SonBinh T. . 2008 . Ligand-elaboration as a strategy for engendering structural diversity in porous metal–organic framework compounds . . 31 . 3672–3674 . 10.1039/B714160B. 18665295 .