Sydnone

Chemical structure of sydnone

Sydnone is a mesoionic heterocyclic aromatic chemical compound. Recent computational studies have, however, shown Sydnone and other similar mesoionic compounds to be nonaromatic, "though well-stabilized in two separate regions by electron and charge delocalization."[1] 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.

Discovery

Sydnone was first prepared in 1935 by Earl & Mackney by cyclodehydration of N-Nitroso-N-phenylglycine with acetic anhydride.

Chemical structure

See also

External links

References

  1. Simas, Alfredo (1998). "Are mesoionic compounds aromatic?". Canadian Journal of Chemistry 76: 869–872. doi:10.1139/v98-065.
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