Binding of ion pairs and neutral guests by aryl-extended meso‑p-hydroxyphenyl calix[4]pyrrole : The interplay between three binding sites
Publiceringsår
2023
Upphovspersoner
Pamuła, Małgorzata; Bulatov, Evgeny; Helttunen, Kaisa
Abstrakt
An aryl-extended calix[4]pyrrole with four meso‑p-hydroxyphenyl substituents was investigated as a host for chloride, acetate, and benzoate anions. Crystal structures of pyridinium and imidazolium chloride complexes were obtained in which chloride ions are hydrogen bonded exo-cavity to the upper rim hydroxyl groups, and the aromatic cations are bound to the shallow cavity of the host. Furthermore, the calix[4]pyrrole formed a hydrogen bonded dimeric capsule templated by inclusion of adiponitrile guest in the endo-cavity binding site. NMR titrations revealed the preference of the OH groups of the host to bind anionic guests in solution. Benzoate anion had the highest binding constant (4 700 M−1) in acetonitrile. Density functional theory (DFT) calculations indicated that the exo-cavity complex with chloride anions was favoured by 23.2 kJ/mol over the endo-cavity complex, whereas the energies of endo- and exo-cavity benzoate complexes were of similar magnitude due to dispersion interactions between the host and the guest.
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Publikationstyp
Publikationsform
Artikel
Moderpublikationens typ
Tidning
Artikelstyp
En originalartikel
Målgrupp
VetenskapligKollegialt utvärderad
Kollegialt utvärderadUKM:s publikationstyp
A1 Originalartikel i en vetenskaplig tidskriftPublikationskanalens uppgifter
Journal
Förläggare
Volym
1273
Nummer
5
Artikelnummer
134268
ISSN
Publikationsforum
Publikationsforumsnivå
1
Öppen tillgång
Öppen tillgänglighet i förläggarens tjänst
Ja
Öppen tillgång till publikationskanalen
Delvis öppen publikationskanal
Parallellsparad
Ja
Övriga uppgifter
Vetenskapsområden
Kemi
Nyckelord
[object Object],[object Object],[object Object],[object Object],[object Object]
Publiceringsland
Nederländerna
Förlagets internationalitet
Internationell
Språk
engelska
Internationell sampublikation
Nej
Sampublikation med ett företag
Nej
DOI
10.1016/j.molstruc.2022.134268
Publikationen ingår i undervisnings- och kulturministeriets datainsamling
Ja