Naslov
Uniquely malleable electronic structure of chloranilic acid

Autori
Molčanov, Krešimir ; Jelsch, Christian ; Wenger, Emmanuel ; Jurić, Marijana ; Androš Dubraja, Lidija ; Kojić-Prodić, Biserka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
24th Croatian-Slovenian Crystallographic Meeting, Book of Abstracts / Cetina, Mario - Zagreb : Hrvatska akademija znanosti i umjetnosti (HAZU), 2016, 31-31

Skup
24th Croatian-Slovenian Crystallographic Meeting

Mjesto i datum
Bol, Hrvatska, 21.09.2016. - 25.09.2016

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Nije recenziran

Ključne riječi
chloranilic acid ; electronic structure ; X-ray charge density

Sažetak
Chloranilic acid is a quinoid compound with very diverse chemical behaviour: it is a good ligand, proton donor and acceptor, and also able to form unusually strong π-interactions. The reason for its versatility is its especially malleable π-electron system, which can adopt various degrees of delocalisation, depending on ionisation and molecular environment. Therefore, its neutral form is a typical para-quinone, while its dianion has two delocalised systems separated by two single C-C bonds. The mono anion, however, has a delocalised system over a half of the ring, while the other half has distinguishable single and double bonds. It can also bind to metals either as a bridging (bis)bidentate ligand, which has a dianion-like structure or as a terminal bidentate ligand with an ortho-quinoid structure. Differences in molecular geometry, related to changes of electronic structure, affect significantly IR spectra: its C-C and C-O stretching bands display a variety of red- and blue-shifts. Herein, we present a detailed X-ray charge density study of the electron delocalisation in all five different forms of the chloranilic acid. Electron density at the bond critical points is a more accurate measurement of bond order (and therefore electron delocalisation) which complements previous data on bond lengths and IR bands. Also, mapping of the electrostatic potential indicates electron-rich and electron-poor areas in the molecule, corresponding to single (electron-poor), double and delocalised bonds (electron-rich).

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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