Dipolar five- (possibly six-) membered @H02798@ in which both the negative and the positive charge are delocalized, for which a totally covalent structure cannot be written, and which cannot be represented satisfactorily by any one polar structure. The formal positive charge is associated with the ring atoms, and the formal negative charge is associated with ring atoms or an exocyclic nitrogen or chalcogen atom. Mesoionic compounds are a subclass of @B00637@.
See also:
PAC, 1995, 67, 1307. (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1349 [Terms] [Paper]