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

Mark Mascal, Alan Armstrong, Michael D. Bartberger

Research output: Contribution to journalArticle

505 Citations (Scopus)

Abstract

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
Volume124
Issue number22
DOIs
StatePublished - Jun 5 2002

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Triazines
Anions
Negative ions
Azides
Hydrogen Bonding
Complexation
Fluorides
Chlorides
Hydrogen bonds
Electrons
Ions

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Anion-aromatic bonding : A case for anion recognition by π-acidic rings. / Mascal, Mark; Armstrong, Alan; Bartberger, Michael D.

In: Journal of the American Chemical Society, Vol. 124, No. 22, 05.06.2002, p. 6274-6276.

Research output: Contribution to journalArticle

Mascal, Mark ; Armstrong, Alan ; Bartberger, Michael D. / Anion-aromatic bonding : A case for anion recognition by π-acidic rings. In: Journal of the American Chemical Society. 2002 ; Vol. 124, No. 22. pp. 6274-6276.
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