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Updated: Sep 25, 2025

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
Published on: September 5, 2018
New water-soluble isoxazole-linked 1,3,4-oxadiazole derivative with delocalized positive charge
Urszula Bąchor1, Ewa Drozd-Szczygieł1, Remigiusz Bąchor2
1Department of Organic Chemistry, Faculty of Pharmacy, Wroclaw Medical University Borowska 211A 50-556 Wroclaw Poland ewa.drozd-szczygiel@umed.wroc.pl.
Abstract:
Herein we present a synthesis and characterization of a new and unique low-weight heterocyclic compound 5-amino-2-(5-amino-3-methyl-1,2-oxazol-4-yl)-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-ylium bromide with the unusual electron charge delocalization owing the local positive charge at the carbon atom of oxadiazole moiety. X-ray single crystal of C7H10N5O2·Br- showed the molecule crystalized in monoclinic, space group P21/c. Both five membered rings are planar and twisted forming the ring motif with the counter ion where H⋯Br interactions are one of the dominant. The presented compound is characterized by high ionization efficiency in ESI-MS mode and undergoes dissociation within oxadiazole moiety under ESI-MS/MS conditions even under low collision energies. The presented compound is an interesting example of heterocyclic stable carbocation which may serve as a new lead structure.
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