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

G K Surya Prakash; Fang Wang; Nan Shao; Thomas Mathew; Golam Rasul; Ralf Haiges; Timothy Stewart; George A Olah

doi:10.1002/anie.200901414

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

Angew Chem Int Ed Engl. 2009;48(29):5358-62. doi: 10.1002/anie.200901414.

Authors

G K Surya Prakash¹, Fang Wang, Nan Shao, Thomas Mathew, Golam Rasul, Ralf Haiges, Timothy Stewart, George A Olah

Affiliation

¹ Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA-90089-1661, USA. [email protected]

PMID: 19572305
DOI: 10.1002/anie.200901414

Abstract

Fluoro power: In agreement with theoretical studies on alpha-fluorocarbanions an X-ray crystal structure shows the alpha-fluorobis(phenylsulfonyl)methide anion adopts a pyramidal configuration (see picture). High-level calculations and NMR spectroscopy studies demonstrate that electron-withdrawing substituents play a crucial role in modulating the properties of bis(phenylsulfonyl)methide anions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anions / chemistry
Crystallography, X-Ray*
Hydrocarbons, Fluorinated / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Sulfones / chemistry*

Substances

Anions
Hydrocarbons, Fluorinated
Sulfones
alpha-fluorobis(phenylsulfonyl)methide