A push-pull olefin is a type of olefin characterized by an electron-withdrawingsubstituent 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.
Referencesedit
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 [1]open access publication
push, pull, olefin, other, uses, push, pull, push, pull, disambiguation, push, pull, olefin, type, olefin, characterized, electron, withdrawing, substituent, side, double, bond, electron, donating, substituent, other, side, this, makes, bond, very, polarized, . For other uses of push pull see Push pull disambiguation 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 editEthyl 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 1 open access publicationSee also editLeimgruber Batcho indole synthesis Application of push pull olefins in molecular logic gates Retrieved from https en wikipedia org w index php title Push pull olefin amp oldid 1145696366, wikipedia, wiki, book, books, library,
