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A combined crystallographic and theoretical study of weak intermolecular interactions in crystalline squaric acid esters and amides

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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.

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PROHENS LÓPEZ, Rafael, PORTELL BUESO, Anna, FONT BARDIA, Ma. mercedes, BAUZÁ, Antonio, FRONTERA, Antonio. A combined crystallographic and theoretical study of weak intermolecular interactions in crystalline squaric acid esters and amides. _Crystengcomm_. 2017. Vol. 19, núm. 22, pàgs. 3071-3077. [consulta: 8 de gener de 2026]. ISSN: 1466-8033. [Disponible a: https://hdl.handle.net/2445/163714]

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