Stable Molecular Complex of Squaric Acid with 2-(Quinuclidinium)propionate

Zofia Dega-Szafran; Andrzej Katrusiak; Miroslaw Szafran

doi:10.1071/CH13121

RESEARCH ARTICLE

Previous Contents Vol 66(7)

Stable Molecular Complex of Squaric Acid with 2-(Quinuclidinium)propionate

Zofia Dega-Szafran ^A ^B , Andrzej Katrusiak ^A and Miroslaw Szafran ^A

+ Author Affiliations

- Author Affiliations

^A Faculty of Chemistry, Adam Mickiewicz University, 61-614 Poznań, Poland.

^B Corresponding author. Email: degasz@amu.edu.pl

Australian Journal of Chemistry 66(7) 836-842 https://doi.org/10.1071/CH13121
Submitted: 15 March 2013 Accepted: 17 April 2013 Published: 17 May 2013

Abstract

Squaric acid (3,4-dihydroxy-3-cyclobuten-1,2-dione, H₂SQ) forms a complex with 2-(quinuclidinium)propionate (QNPr). In crystals, the molecules of H₂SQ and zwitterions of QNPr are bridged by two strong non-equivalent O–H⋯O hydrogen bonds of 2.476(2) and 2.482(1) Å. The complex is investigated by X-ray diffraction, FTIR, and NMR techniques, and the results are supported by density functional theory calculations. The solid-state aggregation is consistent with the NMR results, recorded for an aqueous solution, and is also reproduced for the structure optimized at the B3LYP/6-311++G(d,p) level of theory. The calculated IR frequencies for the optimized structure have been used for the assignment of the experimental FTIR spectrum, where the broad absorption at ~2400 cm^–1 corresponds to the short asymmetric OH⋯O bonds.

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Stable Molecular Complex of Squaric Acid with 2-(Quinuclidinium)propionate

Abstract

References

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