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A persistent alpha-fluorocarbanion and its analogues: preparation, characterization, and computational study.

G K Surya Prakash¹, Fang Wang, Nan Shao

¹Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA-90089-1661, USA. gprakash@usc.edu

Angewandte Chemie (International Ed. in English)

|July 3, 2009

Summary

The pyramidal configuration of alpha-fluorocarbanions is confirmed by X-ray crystallography. Electron-withdrawing groups significantly influence the properties of bis(phenylsulfonyl)methide anions.

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Area of Science:

Organometallic Chemistry
Crystallography
Computational Chemistry

Background:

Alpha-fluorocarbanions are important synthetic intermediates.
Theoretical studies suggested a pyramidal configuration for these anions.
Bis(phenylsulfonyl)methide anions are known for their unique electronic properties.

Purpose of the Study:

To experimentally determine the structure of an alpha-fluorocarbanion.
To investigate the influence of electron-withdrawing substituents on carbanion properties.

Main Methods:

X-ray crystallography was used to obtain the crystal structure of the alpha-fluorobis(phenylsulfonyl)methide anion.
High-level computational calculations were performed.
Nuclear Magnetic Resonance (NMR) spectroscopy was employed.

Main Results:

The X-ray crystal structure confirmed a pyramidal configuration for the alpha-fluorobis(phenylsulfonyl)methide anion.
Computational and NMR studies demonstrated that electron-withdrawing substituents modulate the anion's properties.
The findings align with previous theoretical predictions.

Conclusions:

Experimental evidence supports the theoretical model of pyramidal alpha-fluorocarbanions.
Electron-withdrawing substituents are key to tuning the characteristics of bis(phenylsulfonyl)methide anions.
This study provides valuable insights into the structure-property relationships of fluorinated carbanions.