What question did this study set out to answer?

To characterize the noncovalent bonding interactions between negatively charged anions and the aryl centroid of electron-deficient aromatic rings.

May 11, 2002Journal of the American Chemical Society

Anion−Aromatic Bonding: A Case for Anion Recognition by π-Acidic Rings

View Full Paper

Ask AI

Bookmark

Authors

MMMark MascalUniversity of California, Davis AAAlan ArmstrongUnited States Army Medical Command MBMichael D. BartbergerFate Therapeutics (United States)

Discussion

Member takes

Implication

Computational modeling reveals noncovalent anion-aryl centroid bonding in electron-deficient triazines, suggesting novel designs for synthetic anion receptors.

Key Points

To characterize the noncovalent bonding interactions between negatively charged anions and the aryl centroid of electron-deficient aromatic rings.
Conducted ab initio quantum chemical calculations at the MP2 level of theory.
Modeled interactions between 1,3,5-triazine or trifluoro-1,3,5-triazine and three different anions: fluoride, chloride, and azide.
Identified stable energy minima representing direct noncovalent binding between anions and the central ring face of electron-deficient triazines.
Located competitive interaction geometries involving carbon-hydrogen hydrogen bonding, nucleophilic addition pre-complexes, and pi-stacking with azide.
Demonstrated that fluorinated triazines also sustain aryl centroid complexation alongside reactive nucleophilic complexes.

Cite This Study

Mascal et al. (2002) studied this question.

synapsesocial.com/papers/6a74cb2154045e727a090fad https://doi.org/10.1021/ja017449s

View Full Paper

Ask AI

Bookmark

Implication

Computational modeling reveals noncovalent anion-aryl centroid bonding in electron-deficient triazines, suggesting novel designs for synthetic anion receptors.

Anion−Aromatic Bonding: A Case for Anion Recognition by π-Acidic Rings

Discussion

Member takes

Implication

Key Points

Cite This Study

Anion−Aromatic Bonding: A Case for Anion Recognition by π-Acidic Rings

Discussion

Member takes

Implication

Key Points

Cite This Study

Also Consider

Also Consider