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Crystals 2016, 6(11), 139; doi:10.3390/cryst6110139

Structural and Theoretical Evidence of the Depleted Proton Affinity of the N3-Atom in Acyclovir

Department of Inorganic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, Spain
Department of Chemistry, Faculty of Science, University of the Balearic Islands, Crta. de Valldemossa km 7.5, 07122 Palma de Mallorca (Baleares), Spain
Author to whom correspondence should be addressed.
Academic Editors: Thomas Doert and Mathias Wickleder
Received: 27 September 2016 / Revised: 20 October 2016 / Accepted: 21 October 2016 / Published: 29 October 2016
(This article belongs to the Special Issue Crystal Structure of Complex Compounds)
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The hydronium salt (H3O)2[Cu(N7–acv)2(H2O)2(SO4)2]·2H2O (1, acv = acyclovir) has been synthesized and characterized by single-crystal X-ray diffraction and spectral methods. Solvated Cu(OH)2 is a by-product of the synthesis. In the all-trans centrosymmetric complex anion, (a) the Cu(II) atom exhibits an elongated octahedral coordination; (b) the metal-binding pattern of acyclovir (acv) consists of a Cu–N7(acv) bond plus an (aqua)O–H···O6(acv) interligand interaction; and (c) trans-apical/distal sites are occupied by monodentate O-sulfate donor anions. Neutral acyclovir and aqua-proximal ligands occupy the basal positions, stabilizing the metal binding pattern of acv. Each hydronium(1+) ion builds three H-bonds with O–sulfate, O6(acv), and O–alcohol(acv) from three neighboring complex anions. No O atoms of solvent water molecules are involved as acceptors. Theoretical calculations of molecular electrostatic potential surfaces and atomic charges also support that the O-alcohol of the N9(acv) side chain is a better H-acceptor than the N3 or the O-ether atoms of acv. View Full-Text
Keywords: copper(II); mixed-ligand; hydronium; crystal structure; DFT calculations; interligand interactions copper(II); mixed-ligand; hydronium; crystal structure; DFT calculations; interligand interactions

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Vílchez-Rodríguez, E.; Pérez-Toro, I.; Bauzá, A.; Matilla-Hernández, A. Structural and Theoretical Evidence of the Depleted Proton Affinity of the N3-Atom in Acyclovir. Crystals 2016, 6, 139.

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