Binding of ion pairs and neutral guests by aryl-extended meso‑p-hydroxyphenyl calix[4]pyrrole : The interplay between three binding sites
Pamuła, M., Bulatov, E., & Helttunen, K. (2023). Binding of ion pairs and neutral guests by aryl-extended meso‑p-hydroxyphenyl calix[4]pyrrole : The interplay between three binding sites. Journal of Molecular Structure, 1273(5), Article 134268. https://doi.org/10.1016/j.molstruc.2022.134268
Julkaistu sarjassa
Journal of Molecular StructurePäivämäärä
2023Oppiaine
Epäorgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaNanoscience CenterOrgaaninen kemiaInorganic ChemistryInorganic and Analytical ChemistryNanoscience CenterOrganic ChemistryTekijänoikeudet
© 2022 The Author(s). Published by Elsevier B.V.
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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Julkaisija
Elsevier BVISSN Hae Julkaisufoorumista
0022-2860Asiasanat
Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/159126000
Metadata
Näytä kaikki kuvailutiedotKokoelmat
Rahoittaja(t)
Suomen AkatemiaRahoitusohjelmat(t)
Akatemiatutkija, SA; Akatemiatutkijan tutkimuskulut, SALisätietoja rahoituksesta
This work was supported by Academy of Finland (grants 309910, 314287, 335685).Lisenssi
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