Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds Velo Gala, Inmaculada González Pérez, Josefa María Domínguez Martín, Alicia Acyclovir Molecular recognition DFT Non-covalent interactions H-bonds This research was funded by Agencia Estatal de Investigación, Ministerio de Ciencia, Innovación y Universidades (MICIU) from Spain and co-funded with FEDER-EU (Projects No. PGC2018-102047-B-I00 and CTQ2017-85821-R); Junta de Andalucía (FQM-283), and University of Granada (Project ref. PPJIA2019-03). The data presented in this study are available in this article or supplementary material. The contribution of the undergraduate student Elisabet J. Muela Morales as well as the technical and human support provided by SGIker (UPV/EHU) is gratefully acknowledged. A.D.-M. and M.B.-O. acknowledge support from Cost Action CA18202—Network for Equilibria and Chemical Thermodynamics Advanced Research. The synthetic nucleoside acyclovir is considered an outstanding model of the natural nucleoside guanosine. With the purpose of deepening on the influence and nature of non-covalent interactions regarding molecular recognition patterns, three novel Cu(II) complexes, involving acyclovir (acv) and the ligand receptor N-(2-hydroxyethyl)ethylenediamine (hen), have been synthesized and thoroughly characterized. The three novel compounds introduce none, one or two acyclovir molecules, respectively. Molecular recognition has been evaluated using single crystal X-ray diffraction. Furthermore, theoretical calculations and other physical methods such as thermogravimetric analysis, infrared and UV-Vis spectroscopy, electron paramagnetic resonance and magnetic measurements have been used. Theoretical calculations are in line with experimental results, supporting the relevance of the [metal-N7(acv) + H-bond] molecular recognition pattern. It was also shown that (hen)O-H group is used as preferred H-donor when it is found within the basal coordination plane, since the higher polarity of the terminal (hen)O-H versus the N-H group favours its implication. Otherwise, when (hen)O-H occupies the distal coordination site, (hen)N-H groups can take over. 2021-04-28T12:22:27Z 2021-04-28T12:22:27Z 2021-03-09 info:eu-repo/semantics/article Velo-Gala, I.; Barceló-Oliver, M.; Gil, D.M.; González-Pérez, J.M.; Castiñeiras, A.; Domínguez-Martín, A. Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds. Pharmaceuticals 2021, 14, 244. [https://doi.org/10.3390/ph14030244] http://hdl.handle.net/10481/68169 10.3390/ph14030244 eng http://creativecommons.org/licenses/by/3.0/es/ info:eu-repo/semantics/openAccess Atribución 3.0 España MDPI