Original scientific paper

https://doi.org/10.5562/cca3248

Synthesis and Anion Binding Assessment of Novel Adamantane Amidopyrroles

Marija Alešković ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, 10002, Zagreb, Croatia
Mladena Glavaš ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, 10002, Zagreb, Croatia
Marina Šekutor ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, 10002, Zagreb, Croatia
Kata Mlinarić-Majerski orcid.org/0000-0001-6282-1662 ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, 10002, Zagreb, Croatia

Abstract

Two new adamantane anion receptors with amidopyrrole side arms were prepared and their anion binding ability in DMSO solutions with TBA salts (Cl–, AcO– and H2PO4–) was investigated by UV/Vis spectroscopy. After calculating the corresponding association constants of receptor-anion complexes, it became apparent that only one amidopyrrole side arm was engaged in complexation. These experimental findings were rationalized using computational tools and the binding mode was proposed. In addition to the found 1 : 1 stoichiometry, we showed that the studied receptors bind oxo-anions (H2PO4– and AcO–) more strongly than spherical halogenide (Cl–) anions.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

anion receptors; adamantane amidopyrroles; binding assessment

Hrčak ID:

198488

URI

https://hrcak.srce.hr/198488

Publication date:

29.12.2017.

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