Please use this identifier to cite or link to this item:
https://hdl.handle.net/2445/163714
Title: | A combined crystallographic and theoretical study of weak intermolecular interactions in crystalline squaric acid esters and amides |
Author: | Prohens López, Rafael Portell Bueso, Anna Font Bardia, Ma. Mercedes Bauzá, Antonio Frontera, Antonio |
Keywords: | Cristal·lografia Èsters Amides Crystallography Esters Amides |
Issue Date: | 8-May-2017 |
Publisher: | Royal Society of Chemistry |
Abstract: | We report the synthesis and X-ray solid state structures of five squaric acid derivatives, i.e. a zwitterionic compound, namely 3-hydroxy-4-(2-pyridin-2-yl-ethylamino)cyclobut-3-ene-1,2-dione (1), a squaramide monoester, 3-ethoxy-4-(2-pyridin-2-yl-ethylamino)cyclobut-3-ene-1,2-dione (2), two differently solvated (EtOH and DMSO/water) disquaramides 3,4-bisIJ(4-hydroxyphenethyl)amino)cyclobut-3-ene-1,2-dione (3 and 4, respectively), and a mixed hydrogen squarate and disquarate 2-(2-aminoethyl)pyridinium salt (5). All compounds form interesting supramolecular assemblies in the solid state that have been analyzed using high level DFT calculations and Bader's theory of 'atoms-in-molecules'. An intricate combination of ionpair and H-bonding interactions along with π-π stacking and anion-π contacts of the cyclobutenedione rings is crucial for the formation of the supramolecular assemblies in the solid state. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1039/c7ce00556c |
It is part of: | Crystengcomm, 2017, vol. 19, num. 22, p. 3071-3077 |
URI: | https://hdl.handle.net/2445/163714 |
Related resource: | https://doi.org/10.1039/c7ce00556c |
ISSN: | 1466-8033 |
Appears in Collections: | Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada) |
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