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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

1
Department of Inorganic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, Spain
2
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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Abstract

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
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MDPI and ACS Style

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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