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

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.

SUBMITTER: Bachor U

PROVIDER: S-EPMC9040910 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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

Bąchor Urszula U Drozd-Szczygieł Ewa E Bąchor Remigiusz R Jerzykiewicz Lucjan L Wieczorek Robert R Mączyński Marcin M

RSC advances 20210903 47

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/ ...[more]

PMID: 35479548

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