Anion-aromatic bonding: A case for anion recognition by π-acidic rings

Mark Mascal, Alan Armstrong, Michael D. Bartberger

Research output: Contribution to journalArticlepeer-review

544 Scopus citations


The basis for unprecedented noncovalent bonding between anions and the aryl centroid of electron-deficient aromatic rings has been demonstrated by an ab initio study of the interaction between 1,3,5-triazine and the fluoride, chloride, and azide ion at the MP2 level of theory. Minima are also located corresponding to C-H···X- hydrogen bonding, reactive complexes for nucleophilic attack on the triazine ring, and π-stacking interactions (with azide). Trifluoro-1,3,5-triazine also participates in aryl centroid complexation and forms nucleophilic reactive complexes with anions. This novel mode of bonding suggests the development of new cyclophane-type receptors for the recognition of anions.

Original languageEnglish (US)
Pages (from-to)6274-6276
Number of pages3
JournalJournal of the American Chemical Society
Issue number22
StatePublished - Jun 5 2002

ASJC Scopus subject areas

  • Chemistry(all)


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