New water-soluble isoxazole-linked 1,3,4-oxadiazole derivative with delocalized positive charge.

Autor: Bąchor U; Department of Organic Chemistry, Faculty of Pharmacy, Wroclaw Medical University Borowska 211A 50-556 Wroclaw Poland ewa.drozd-szczygiel@umed.wroc.pl., Drozd-Szczygieł E; Department of Organic Chemistry, Faculty of Pharmacy, Wroclaw Medical University Borowska 211A 50-556 Wroclaw Poland ewa.drozd-szczygiel@umed.wroc.pl., Bąchor R; Faculty of Chemistry, University of Wroclaw F. Joliot-Curie 14 50-383 Wrocław Poland remigiusz.bachor@chem.uni.wroc.pl., Jerzykiewicz L; Faculty of Chemistry, University of Wroclaw F. Joliot-Curie 14 50-383 Wrocław Poland remigiusz.bachor@chem.uni.wroc.pl., Wieczorek R; Faculty of Chemistry, University of Wroclaw F. Joliot-Curie 14 50-383 Wrocław Poland remigiusz.bachor@chem.uni.wroc.pl., Mączyński M; Department of Organic Chemistry, Faculty of Pharmacy, Wroclaw Medical University Borowska 211A 50-556 Wroclaw Poland ewa.drozd-szczygiel@umed.wroc.pl.
Jazyk: angličtina
Zdroj: RSC advances [RSC Adv] 2021 Sep 03; Vol. 11 (47), pp. 29668-29674. Date of Electronic Publication: 2021 Sep 03 (Print Publication: 2021).
DOI: 10.1039/d1ra05116d
Abstrakt: 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 C 7 H 10 N 5 O 2 ·Br - showed the molecule crystalized in monoclinic, space group P 2 1 / 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.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE
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