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Adamantane bisurea derivatives: anion binding in the solution and in the solid state

Blažek, Vesna; Molčanov, Krešimir; Mlinarić-Majerski, Kata; Kojić-Prodić, Biserka; Basarić, Nikola (2013) Adamantane bisurea derivatives: anion binding in the solution and in the solid state. Tetrahedron, 69 (2). pp. 517-526. ISSN 0040-4020

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Abstract

1, 3-Bis-(3-arylureido)adamantane receptors, bearing phenyl (5, 6), 1-naphthyl (7, 8) and 9-anthryl (9) fluorophore, were synthesized. Their ability for complexation with F-, Cl-, Br-, OAc-, NO3- HSO4-, and H2PO4- in solution was investigated by UV-vis and fluorescence spectrophotometry. The binding was compared to that of 2-naphthyl bisurea derivatives with flexible spacers (bearing propylene or pentalene, 2 and 4) and rigid adamantane analogues (1 and 3). In solution, the receptors form stable complexes with all anions except with NO3-. The complexation ability in CH3CN correlates with the basicity of anion and the acidity of the urea N-H, whereas in DMSO the complexes stability variations are less pronounced. The X-ray structure of receptor 1 indicates that incorporation of the adamantane moiety preorganizes the receptor in a tweezer-like conformation for the optimal formation of hydrogen bonding network and high selectivity for H2PO4- anion. Incorporation of the methylene spacers between the adamantane and the urea additionally increases stability of the complexes with anions. X-ray structural analysis was performed on the following complexes: 1∙Bu4NH2PO4, 3∙Bu4NH2PO4, 5∙Bu4NH2PO4∙4H2O, and 5∙Bu4NOAc∙3H2O. All H2PO4- complexes include extensive receptor•••H2PO4- hydrogen bonds, essential for the anion recognition, as well as H2PO4-•••H2PO4- hydrogen bonds.

Item Type: Article
Uncontrolled Keywords: adamantanes; anion receptors; fluorescence titration; UV-vis titration; ureas; X-ray structural analysis
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
Projects:
Project titleProject leaderProject codeProject type
Cage Compounds: Building Blocks for Molecular Architecture (Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima)Kata Majerski098-0982933-2911MZOS
Protein-ligand interactions at atomic level (Protein-ligand međudjelovanja na atomnoj razini)Marija Luić098-1191344-2943MZOS
Depositing User: Vesna Blažek Bregović
Date Deposited: 03 Feb 2016 12:34
Last Modified: 03 Feb 2016 12:34
URI: http://fulir.irb.hr/id/eprint/2451
DOI: 10.1016/j.tet.2012.11.030

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