Sydnones are mesoionic heterocyclic chemical compounds possessing a 1,2,3-oxadiazole core with a keto group in the 5 position.[1][2][3] Like other mesoionic compounds they are di-polar, possessing both positive and negative charges which are delocalized across the ring. Recent computational studies have indicated that sydnones and other similar mesoionic compounds are nonaromatic, "though well-stabilized in two separate regions by electron and charge delocalization."[4] Sydnones are heterocyclic compounds named after the city of Sydney, Australia.
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IUPAC name
2H-Oxadiazol-5-one
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Other names
1,2,3-Oxadiazol-5(2H)-one
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Identifiers | |
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3D model (JSmol)
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Properties | |
C2H2N2O2 | |
Molar mass | 86.050 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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A sydnone imine in which the keto group of sydnone (=O) has been replaced with an imino (=NH) group can be found as a substructure in the stimulant drugs feprosidnine and mesocarb.
Sydnone was first prepared in 1935 by Earl & Mackney by cyclodehydration of N-Nitroso-N-phenylglycine with acetic anhydride.[5] Later work showed that this could be applied fairly generally to the nitrosamines of N-substituted amino acids.[2]
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