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Squaramide

Squaramide is the organic compound with the formula O2C4(NH2)2. Not an amide in the usual sense, it is a derivative of squaric acid wherein the two OH groups are replaced by NH2 groups. Squaramides refer to a large class of derivatives wherein some of the H's are replaced by organic substituents. Exploiting their rigid planar structures, these compounds are of interest as hydrogen-bond donors in supramolecular chemistry and squaramide catalysis. Squaramides exhibit 10-50x greater affinity for halides than do thioureas.

Squaramide is prepared by ammonolysis of diesters of squaric acid: :O2C4(OEt)2 + 2 NH3 → O2C4(NH2)2 + 2 EtOH N-Substituted squaramides are prepared similarly, using amines in place of ammonia.

References

References

  1. (2015). "Bifunctional Amine-Squaramides: Powerful Hydrogen-Bonding Organocatalysts for Asymmetric Domino/Cascade Reactions". Adv. Synth. Catal..
  2. (2021). "Squaric acid as a new chemoselective moiety for mass spectrometry-based metabolomics analysis of amines". RSC Chemical Biology.
  3. (2013). "Be squared: expanding the horizon of squaric acid-mediated conjugations". Chemical Society Reviews.
  4. Storer, R. Ian. (2013). "Squaramide".
  5. (2011). "Squaramides: Physical properties, synthesis and applications". Chemical Society Reviews.
  6. Nathalie Busschaert. (2012). "Squaramides as Potent Transmembrane Anion Transporters". Angew. Chem. Int. Ed..
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ketones enamines cyclobutenes
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