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Anion−Aromatic Bonding: A Case for Anion Recognition by π-Acidic Rings
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[bond]H...X(-) hydrogen bonding, reactive complexes for nucleophilic attack on the triazine ring, and pi-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.
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Cites
Density-functional thermochemistry. III. The role of exact exchange
Becke, A. D. (1993) · The Journal of Chemical Physics · doi:10.1063/1.464913 · Cited by 103,767
Lee, C., Yang, W., & Parr, R. G. (1988) · Physical Review B · doi:10.1103/physrevb.37.785 · Cited by 100,874
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He, Q., Vargas-Zúñiga, G. I., Kim, S. H., Kim, S. K., & Sessler, J. L. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00734 · Cited by 319
Engineering Hydrogel Adhesion for Biomedical Applications via Chemical Design of the Junction
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Metadata
- Authors
- Mascal, M., Armstrong, A., & Bartberger, M. D.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-05-11
- Volume
- 124
- Issue
- 22
- Pages
- 6274-6276
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2022407184
- Cited by
- 639
- References
- 2
- FWCI
- 12.64
- Type
- journal article
- Language
- en
- Open access
- closed
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