Novel Reactions of 1, 2-Disubstituted Benzenes Coordinated to Cobalt(III): Neighboring-Group Participation

Robert J. Balahura, William L. Purcell

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The pentaamminecobalt(III) complex of 1,2-dicyanobenzene reacts with a stoichiometric amount of base to give the coordinated carboxamido complex (NH3)5Co(2-carboxamidobenzonitrile)2+. The latter complex cyclizes in base to the pentaamminecobalt(III) complex of 1-oxo-3-iminoisoindolin-2-yl. However, in acid solution the coordinated amide complex undergoes an intramolecular rearrangement to form the coordinated nitrile-free amide compound (NH3)5Co(2-cyanobenzamide)3+. This nitrile complex is rapidly hydrolyzed, the reaction involving intramolecular catalysis by the free amide group. The product of the hydrolysis reaction, (NH3)5Co(2-carboxamidobenzamide)2+, cyclizes in acidic solution to (NH3)5Co(1-oxo-3-iminoisoindoline)3+ where the metal is coordinated to the exocyclic nitrogen (3 position). The characterization of the above complexes is described, and mechanisms for their formation are considered.

Original languageEnglish (US)
Pages (from-to)937-941
Number of pages5
JournalInorganic Chemistry
Issue number4
StatePublished - Jan 1 1979


ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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