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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
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:
It is part of: Crystengcomm, 2017, vol. 19, num. 22, p. 3071-3077
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ISSN: 1466-8033
Appears in Collections:Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)

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