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http://hdl.handle.net/2445/163123
Title: | Polymorphism in secondary squaramides: on the importance of π-interactions involving the four membered ring |
Author: | Prohens López, Rafael Portell Bueso, Anna Vallcorba, Oriol Font Bardia, Ma. Mercedes Bauzá, Antonio Frontera, Antonio |
Keywords: | Polimorfisme (Cristal·lografia) Química supramolecular Polymorphism (Crystallography) Supramolecular chemistry |
Issue Date: | 2018 |
Publisher: | Royal Society of Chemistry |
Abstract: | We report the X-ray solid state structures of four new squaric acid derivatives, i.e. three polymorphs of 3,4-bisIJ(2-(dimethylamino)ethyl)amino)cyclobut-3-ene-1,2-dione (1a-c) and a co-crystal of compound 1 and resorcinol (2). All structures form interesting supramolecular assemblies in the solid state which have been analyzed using high level DFT calculations and molecular electrostatic potential (MEP) surface calculations. A combination of H-bonding and π-π stacking interactions of the cyclobutenedione rings are crucial for the formation of the supramolecular assemblies in the solid state. Moreover, unusual antiparallel CO⋯CO interactions observed in the X-ray structure of one of the polymorphs of 1 and the lp-π interactions between one oxygen atom of resorcinol and the squaramide ring in 2 have been characterized using Bader's theory of 'atoms-in-molecules' (AIM). |
Note: | Versió postprint del document publicat a: https://doi.org/10.1039/c7ce01945a |
It is part of: | Crystengcomm, 2018, vol. 20, num. 2, p. 237-244 |
URI: | http://hdl.handle.net/2445/163123 |
Related resource: | https://doi.org/10.1039/c7ce01945a |
ISSN: | 1466-8033 |
Appears in Collections: | Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada) |
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