PMID: 11925210Apr 2, 2002Paper

A novel crown ether generation containing different heteroaromatic cations: synthesis, characterization, solid-phase (13)C NMR, X-ray crystal structure, and selective amino acid recognition

The Journal of Organic Chemistry
Abolghasem MoghimiHamid Rahbarnoohi

Abstract

The synthesis and structural characterization of a novel generation of crown ethers, 3, 5 and 6 containing pyrilium, thiopyrilium, and pyridinium subunits, respectively, are reported. The crown ether unit is potentially capable of forming host-guest complexes with inorganic and organic cations, while the heteroaromatic cationic unit is suitable to bind with anions. A variety of physicochemical methods including electrospray mass spectrometry, UV-vis spectroscopy, solution and solid-phase NMR, and X-ray crystallography were applied for structural characterization of the new crown ether derivatives. The (1)H and (13)C NMR studies indicate rapid rotation of the B9C3 unit about the C-C bond that connects the two units to each other. Single crystals for 3, 4, and 5 were successfully obtained, and their X-ray crystal structures were resolved. The perchlorate anion in 3 (orthorhombic, space group P2(1)2(1)2(1)) and 5 (orthorhombic, space group P2(1)) is far from O(+) and close to S(+). The solid-phase structure of 3 and 5 show small deviation from planarity for the four aromatic rings, whereas two of the aromatic rings in 4 are out of heteroaromatic ring. Spectrophotometric studies in methanol solution revealed that the ligand 3 can b...Continue Reading

References

Jan 1, 1995·Acta Crystallographica. Section A, Foundations of Crystallography·R H Blessing

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Citations

May 27, 2010·Beilstein Journal of Organic Chemistry·Andreas Späth, Burkhard König
Nov 2, 2005·Molecular Genetics and Genomics : MGG·Monique MarilleyJosé Rocca-Serra
May 16, 2019·Physical Chemistry Chemical Physics : PCCP·Elia GruesoR Prado-Gotor
Jul 6, 2014·Journal of Computer-aided Molecular Design·Pavan Kumar PingaliDhananjay Bhattacharyya
Nov 18, 2009·Journal of Biomolecular Structure & Dynamics·Sudipta SamantaDhananjay Bhattacharyya
Jul 30, 2014·Physical Chemistry Chemical Physics : PCCP·Antonio FranconettiFrancisca Cabrera-Escribano
Feb 6, 2020·Chemistry, an Asian Journal·Ignacio Alfonso, Jordi Solà
Oct 30, 2010·Journal of the American Chemical Society·Jérôme FortagePhilippe P Lainé
Sep 13, 2014·Chemical Reviews·Vanderlei G MachadoChristian Reichardt
May 16, 2012·The Journal of Physical Chemistry. a·Yinghong Sheng, Yi Ren

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