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Comprehensive Energetic Scale for Quantitatively Estimating the Fluorinating Potential of N-F Reagents in Electrophilic Fluorinations.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2016 May 20; Vol. 81 (10), pp. 4280-9. Date of Electronic Publication: 2016 May 06. - Publication Year :
- 2016
-
Abstract
- Quantitative knowledge of the fluorinating strength of electrophilic N-F reagents is of crucial importance for rational design and optimization of novel reagents and new reactions. Herein, we report the first systematic computation of fluorinating potentials of 130 electrophilic N-F reagents in two commonly used solvents dichloromethane and acetonitrile in terms of the N-F bond heterolysis energies as expressed by the fluorine plus detachment (FPD) values. The calculated FPD scales of 130 N-F reagents cover a range from 112.3 to 290.4 kcal mol(-1) and 110.9 to 278.4 kcal mol(-1) in dichloromethane and acetonitrile, respectively. This comprehensive FPD database provides a valuable quantitative guide for studying the influence of structural variation on the fluorinating strength of the N-F reagents, opening a door to the rational design of novel reagents with appropriate fluorinating strength for specific purposes. It is demonstrated that the FPD values can reproduce the reactivity order for electrophilic N-F reagents better than other parameters.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 81
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27120313
- Full Text :
- https://doi.org/10.1021/acs.joc.6b00683