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Changes in electron structure of the triple bond in substituted acetylene and diacetylene derivatives.

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dc.abstract.enThe substituent effect is usually considered by means of various Hammett-like substituent constants and is most often related to aromatic systems. Unlike this, we present results of our research on the influence of 27 substituents spanning a wide range of electronic properties, from strongly electron-withdrawing to strongly electron-donating, on the electron structure of X-substituted acetylenes and diacetylenes – thus the systems which until now have practically not been subject of any deeper studies. It is shown that the interaction through triple bond(s) is associated with a significant advantage of resonance effects and that the substituent effect transmitted by the C≡C−C≡C unit is about half of that transmitted by the C≡C unit alone. Substituent X mainly affects the closest carbon atom by means of proximity effect, hence changes of charge on this atom do not follow any substituent constants. The effect on further carbon atoms is much smaller. The presence of the C≡C−C≡C unit withdraws more charge from X than a triple bond alone, and hinders communication between X and the terminal H atom. Comparison of substituent effects to those present in X-substituted benzene derivatives shows that the electronic properties of the terminal hydrogen atom in acetylenes and diacetylenes are most similar to the electronic properties of ortho and para hydrogen atoms in X-substituted benzene derivatives.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorKrygowski, Tadeusz
dc.contributor.authorJabłoński, Mirosław
dc.date.accessioned2024-01-24T19:05:44Z
dc.date.available2024-01-24T19:05:44Z
dc.date.issued2020
dc.description.financePublikacja bezkosztowa
dc.description.number16
dc.description.volume21
dc.identifier.doi10.1002/CPHC.202000378
dc.identifier.issn1439-4235
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/102854
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemPhysChem
dc.relation.pages1847-1857
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleChanges in electron structure of the triple bond in substituted acetylene and diacetylene derivatives.
dc.typeJournalArticle
dspace.entity.typePublication