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Anion - pi bonding

The interaction between the centroid of electron poor aromatic rings (e.g. triazine) and anions (fluoride, chloride, azide) was first described by us.  A high-level theoretical study demonstrated that a bonding interaction existed which was similar in magnitude to the intensively studied aromatic cation-pi bond.  This seminal work has led to numerous studies of related systems and to a series of papers in which the interaction was demonstrated experimentally. 

   

 

Lead references:  

"Anion-Aromatic Bonding: A Case for Anion Recognition by p-Acidic Rings."  M. Mascal, A. Armstrong, M. D. Bartberger, J. Am. Chem. Soc. 2002, 124, 6274.  

“Precedent and Theory Unite in the Hypothesis of a Highly Selective Fluoride Ion Receptor.”  M. Mascal, Angew. Chem. Int. Ed. 2006, 45, 2890.

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