Editing Oxime (section)

==Structure and properties==
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 [[stereoisomer]]ic forms according to the [[E/Z configuration|''E''/''Z'' configuration]]. An older terminology of [[Descriptor (chemistry)#syn, anti|''syn'' and ''anti'']] was used to identify especially aldoximes according to whether the R group was closer or further from the hydroxyl.  Both forms are often stable enough to be separated from each other by standard techniques.

Oximes have three characteristic bands in the [[infrared spectroscopy|infrared spectrum]], whose wavelengths corresponding to the stretching vibrations of its three types of bonds: 3600&nbsp;cm<sup>−1</sup> (O−H), 1665&nbsp;cm<sup>−1</sup> (C=N) and 945&nbsp;cm<sup>−1</sup> (N−O).<ref>{{cite web | work = Virtual Textbook of Organic Chemistry | author = Reusch, W. | publisher = [[Michigan State University]] | title = Infrared Spectroscopy | url = http://www.cem.msu.edu/~reusch/VirtTxtJml/Spectrpy/InfraRed/infrared.htm | access-date = 6 July 2009 | archive-url = https://web.archive.org/web/20100621013212/http://www.cem.msu.edu/~reusch/VirtTxtJml/Spectrpy/InfraRed/infrared.htm | archive-date = 21 June 2010 | url-status = dead }}</ref>

In aqueous solution, aliphatic oximes are 10<sup>2</sup>- to 10<sup>3</sup>-fold more resistant to hydrolysis than analogous hydrazones.<ref>{{Cite journal |last1=Kalia |first1=J. |last2=Raines |first2=R. T. |title=Hydrolytic stability of hydrazones and oximes |journal=Angew. Chem. Int. Ed. |year=2008 |volume=47 |pmid=18712739 |issue=39 |pages=7523–7526 |pmc=2743602 |doi=10.1002/anie.200802651}}</ref>