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Push–pull olefin

A push-pull olefin is a type of olefin characterized by an electron-withdrawing substituent on one side of the double bond and an electron-donating substituent on the other side. This makes the pi bond very polarized. The rotational barrier for a push-pull olefin is lower than that of an ordinary olefin and this makes it an interesting candidate for a molecular switch, for instance azobenzenes. A push-pull configuration also helps to stabilize the double bond because the carbon-carbon bond has considerably less double bond character. For instance, cyclobutadiene is a very unstable molecule but with both olefinic bonds in push-pull configuration (two ester substituents and two tertiary amine substituents) the molecule is stable indeed.

References

Ethyl (2-cyano-3-ethoxyacryloyl)carbamate: irreversible thermal isomerization of a push-pull olefin Kuangsen Sung, Ming-Chi Lin, Pin-Mei Huang, Bo-Ren Zhuang, Robert Sung, Ru-Rong Wu Arkivoc 2005 p. 131 http://arkat-usa.org/ark/journal/2005/I13_General/1380/05-1380D.asp open access publication

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alkene-derivatives organic-chemistry

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