Nitrile Anion Structure and Reactivity

image014Description: The nitrile functional group is a small, under-utilized unit in organic synthesis. However, it has been demonstrated that this functional group can be used in the synthesis of complex organic compounds. In particular the stereochemistry of cis/trans decalin systems. Fundamental insight on how nitrile anions operate is not fully realized. Computational methods are being applied to study these systems

Goals: The goal is to use ab initio methods to elucidate the role solvent and counter-ions have on the structure and reactivity of nitrile anions and how the solvent and counter-ions can be used to direct the stereochemistry of specific reactions involving nitrile anions.


  • Carlier, P. R. et al. Effective Computational Modeling of Constitutional Isomerism and Aggregation States of Explicit Solvates of Lithiated Phenylacetonitrile. Journal of Organic Chemistry, 67 (11), 3832-3840. 2002