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Article . 2017 . Peer-reviewed
License: Wiley Online Library User Agreement
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electron delocalization in electron deficient alkenes and push pull alkenes

Authors: Zdravko Džambaski; Marija Baranac-Stojanović;

electron delocalization in electron deficient alkenes and push pull alkenes

Abstract

AbstractWe have studied π electron delocalization in electron‐deficient alkenes and push‐pull alkenes by means of natural bond orbital analysis at the B3LYP/6‐311+G(d,p) level. The study revealed that the rarely mentioned π electron donation from an electron‐accepting group (Acc) toward the C=C double bond in push‐pull alkenes and electron‐deficient alkenes can provide up to 10 % of total π electron stabilizing energy of a push‐pull system and as much as 45 % in a strongly electron‐deficient tetracyanoethene. The Acc → C=C bond π electron donation is more intense in s‐trans than in s‐cis conformational arrangement, but is less dependent on Z/E isomerism in push‐pull alkenes, being slightly more pronounced in Z isomers. Among different Acc substituents, CN and COO‐ groups contribute the largest percent of stabilizing energy and NO2 the smallest. Increase in the number of Acc groups increases percentage contribution of Acc → C=C bond π electron delocalization to a system stabilization. A difference in π*C=C orbital occupancy between isomers can be related with their chemical reactivity.

Country
Serbia
Related Organizations
Keywords

electron delocalization, electronic structure, electron-deficient alkene, density functional theory, push-pull alkene

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  • citations
    This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
    4
    popularity
    This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
    Average
    influence
    This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
    Average
    impulse
    This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
    Average
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citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
4
Average
Average
Average