Oxime

[1] If the two side-chains on the central carbon are different from each other—either an aldoxime, or a ketoxime with two different "R" groups—the oxime can often have two different geometric stereoisomeric forms according to the E/Z configuration.

An older terminology of syn and anti was used to identify especially aldoximes according to whether the R group was closer or further from the hydroxyl.

Oximes have three characteristic bands in the infrared spectrum, whose wavelengths corresponding to the stretching vibrations of its three types of bonds: 3600 cm−1 (O−H), 1665 cm−1 (C=N) and 945 cm−1 (N−O).

In general, oximes exist as colorless crystals or as thick liquids and are poorly soluble in water.

The Ponzio reaction (1906)[14] concerning the conversion of m-nitrobenzaldoxime to m-nitrophenyldinitromethane using dinitrogen tetroxide was the result of research into TNT analogues:[15] Gentler oxidants give mono-nitro compounds.

Certain amidoximes react with benzenesulfonyl chloride to make substituted ureas in the Tiemann rearrangement:[17][18] In their largest application, an oxime is an intermediate in the industrial production of caprolactam, a precursor to Nylon 6.

[21][22] In 2017 researchers announced a configuration that absorbed up to nine times as much uranyl as previous fibers without saturating.