A 1:1.5 complex of 5,7-dioxo-1,4,8,11-tetraazacyclotetradecane and 2,6-dihydoxyanthraquinone |
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Authors: | Elena V. Basiuk Jacobo Gómez-Lara Vladimir A. Basiuk Rubén Alfredo Toscano |
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Affiliation: | (1) Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior C.U., A. Postal 70-213, 04510 México, D.F, Mexico |
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Abstract: | A complex of 5,7-dioxo-1,4,8,11-tetraazacyclotetradecane (dioxocyclam) and 2,6-dihydoxyanthraquinone (anthraflavic acid) has been obtained. The complex (crystals grown from water-ethanol solution) has a stoichiometry dioxocyclam-anthraflavic acid 1:1:5. C31H32N4O8, chemical formula weight 588.61, triclinic, P – 1, a = 10.542(3) Å, b = 11.936(2) Å, c = 12.206(2) Å, = 104.00(1)°, = 92.68(2)°, = 103.64(2)°, V = 1439.4 (5) Å3, Z = 2, Dx = 1.358 g cm–3. Only one of the two amine N-atoms of the macrocycle is protonated due to very weak acidic properties of 2,6-dihydoxyanthraquinone. Due to the rather poor quality of the crystals and structure refinement, reliable determination of H-bonds is complicated. Nevertheless, several types of H-bonding responsible for the formation of a developed supramolecular network can be suggested: between the protonated amino groups and macrocycle's C=O moieties; between non-protonated amino groups and macrocycle's C=O moieties; between protonated and non-protonated amino groups; between the amide NH and C=O groups of anthraflavic acid; and between protonated and deprotonated hydroxy groups of the acid. Two types of anthraflavic components can be distinguished in the lattice: those having a parallel orientation with respect to the macrocyclic fragments and forming hydrogen bonds with the latter, and those lying in an approximately perpendicular plane and not involved in H-bonding with the macrocycles. |
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Keywords: | 5,7-Dioxo-1,4,8,11-tetraazacyclotetradecane 2,6-dihydoxyanthraquinone hydrogen bonding supramolecular network |
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