Guide to Fluorine NMR for Organic Chemists »

William R. Dolbier, Jr., is the Col. Allen R. and Margaret G. Crow Professor of Chemistry at the University of Florida. He received his BS in chemistry from Stetson University in 1961 and his PhD in organic chemistry from Cornell University in 1965. Following a postdoctoral appointment at Yale University, he joined the faculty at the University of Florida in 1966. Professor Dolbier was the recipient of the 2000 American Chemical Society (ACS) Award for Creative Work in Fluorine Chemistry, and is a past member of the Executive Committee of the Fluorine Division of the ACS.

AN UNPARALLELED ONE-STOP GUIDE TO FLUORINE NMR

Guide to Fluorine NMR for Organic Chemists provides a unique single source on both fluorine NMR and the impact of fluorine substituents on proton and carbon NMR spectra. Helping working chemists overcome the challenges associated with the synthetic methodologies of fluorinated compounds, this guide enables the effective use of these increasingly popular spectroscopic techniques to accurately characterize compounds that contain fluorine.

Following a thorough introduction of fluorinated compounds, chapters in the text cover:

• An overview of fluorine NMR

• The single fluorine substituent

• The CF₂ group

• The trifluoromethyl group

• More heavily fluorinated compounds

• Compounds and substituents with fluorine directly bound to heteroatoms

With unparalleled depth and completeness, the coverage ranges from those compounds containing only a few fluorinated substituents, typically employed in pharmaceutical and agricultural applications, to more heavily fluorinated compounds.

Featuring NMR data for more than 1,000 specific compunds and including more than 100 exemplary spectra, Guide to Fluorine NMR for Organic Chemists gives the working chemist and advanced student an essential tool for understanding cutting-edge NMR techniques and interpreting the resulting spectroscopic data.

PREFACE.

1 GENERAL INTRODUCTION.

1.1. Why Fluorinated Compounds are Interesting.

1.2. Introduction to Fluorine NMR.

References.

2 AN OVERVIEW OF FLUORINE NMR.

2.1. Introduction.

2.2. Fluorine Chemical Shifts.

2.3. Spin-Spin Coupling Constants to Fluorine.

2.4. ¹H Spectra of Fluoroorganic Compounds.

2.5. ¹³C NMR Spectra of Fluoroorganic Compounds.

2.6. Isotope Effects on Chemical Shifts.

2.7. Advanced Topics.

References.

3 THE SINGLE FLUORINE SUBSTITUENT.

3.1. Introduction.

3.2. Saturated Hydrocarbons.

3.3. Influence of Substituents/Functional Groups.

3.4. Carbonyl Functional Groups.

3.5. Nitriles.

3.6. Alkenes with a Single Fluorine Substituent.

3.7. Acetylenic Fluorine.

3.8. Allylic, Propargylic, and Benzylic Fluorides.

3.9. Fluoroaromatics.

3.10. Fluoroheterocycles.

3.11. Other Common Groups with a Single Fluorine Substituent.

References.

4 THE CF₂ GROUP.

4.1. Introduction.

4.2. Saturated Hydrocarbons Containing a CF₂ Group.

4.3. Influence of Substituents/Functional Groups.

4.4. Carbonyl Functional Groups.

4.5. Nitriles.

4.6. Bifunctional CF₂ Compounds.

4.7. Alkenes and Alkynes.

4.8. Benzenoid Aromatics Bearing a CF₂ Group.

4.9. Heteroaromatic CF₂ Groups.

References.

5 THE TRIFLUOROMETHYL GROUP.

5.1. Introduction.

5.2. Saturated Hydrocarbons Bearing a CF₃ Group.

5.3. Influence of Substituents and Functional Groups.

5.4. Carbonyl Compounds.

5.5. Nitriles.

5.6. Bifunctional Compounds.

5.7. Sulfonic Acid Derivatives.

5.8. Allylic and Propargylic Trifluoromethyl Groups.

5.9. Aryl-Bound Trifluoromethyl Groups.

5.10. Heteroaryl-Bound Trifluoromethyl Groups.

References.

6 MORE HIGHLY FLUORINATED GROUPS.

6.1. Introduction.

6.2. The 1,1,2- and 1,2,2-Trifluoroethyl Groups.

6.3. The 1,1,2,2-Tetrafluoroethyl and 2,2,3,3-Tetrafluoropropyl Groups.

6.4. The 1,2,2,2-Tetrafluoroethyl Group.

6.5. The Pentafluoroethyl Group.

6.6. The 2,2,3,3,3-Pentafluoropropyl Group.

6.7. The 1,1,2,3,3,3-Hexafluoropropyl Group.

6.8. The Hexafluoro-iso-Propyl Group.

6.9. The Heptafluoro-n-Propyl Group.

6.10. The Heptafluoro-iso-Propyl Group.

6.11. The Nonafluoro-n-Butyl Group.

6.12. Fluorous Groups.

6.13. 1-Hydro-Perfluoroalkanes.

6.14. Perfluoroalkanes.

6.15. Perfluoro-n-Alkyl Halides.

6.16. Perfluoroalkyl Amines, Ethers, and Carboxylic Acid Derivatives.

6.17. Polyfluoroalkenes.

6.18. Polyfluorinated Aromatics.

6.19. Polyfluoroheterocyclics.

References.

7 COMPOUNDS AND SUBSTITUENTS WITH FLUORIDE DIRECTLY BOUND TO A HETEROATOM.

7.1. Introduction.

7.2. Boron Fluorides.

7.3. Fluorosilanes.

7.4. Nitrogen Fluorides.

7.5. Phosphorous Fluorides.

7.6. Oxygen Fluorides (Hypofluorites).

7.7. Sulfur Fluorides.

7.8. The Pentafluorosulfanyl (SF₅) Group.

7.9. Bromine Trifluoride and Iodine Pentafluoride.

7.10. Aryl Halogen Difluorides and Tetrafluorides.

7.11. Xenon Difluoride.

References.

GENERAL INDEX.

COMPOUND INDEX.