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Following its well-received predecessor, this book offers an essential guide to chemists for understanding fluorine in spectroscopy. With over 1000 compounds and 100 spectra, the second edition adds new data - featuring fluorine effects on nitrogen NMR, chemical shifts, and coupling constants. . Explains how to successfully incorporate fluorine into target molecules and utilize fluorine substituents to structurally characterize organic compounds . Includes new data on nitrogen NMR, focusing on N-15, to portray the influence of fluorine upon nitrogen NMR chemical shifts and coupling constants .…mehr
Following its well-received predecessor, this book offers an essential guide to chemists for understanding fluorine in spectroscopy. With over 1000 compounds and 100 spectra, the second edition adds new data - featuring fluorine effects on nitrogen NMR, chemical shifts, and coupling constants. . Explains how to successfully incorporate fluorine into target molecules and utilize fluorine substituents to structurally characterize organic compounds . Includes new data on nitrogen NMR, focusing on N-15, to portray the influence of fluorine upon nitrogen NMR chemical shifts and coupling constants . Expands on each chapter from the first edition with additional data and updated discussion from recent findings . "The flawless ordering of material covered in this stand-alone volume is such that information can be found very easily." - Angewandte Chemie review of the first edition, 2010
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Autorenporträt
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.
Inhaltsangabe
PREFACE xv
1 GENERAL INTRODUCTION 1
1.1. Why Fluorinated Compounds are Interesting? / 1
1.1.1. Steric Size / 1
1.1.2. Polar Effects / 2
1.1.3. Effect of Fluorine Substituents on Acidity and Basicity of Compounds / 2
1.1.4. Effect of Fluorinated Substituents on Lipophilicity of Molecules / 3
1.1.5. Other Effects / 4
1.1.6. Analytical Applications in Biomedicinal Chemistry / 4
1.2. Introduction to Fluorine NMR / 5
1.2.1. Chemical Shifts / 5
1.2.2. Coupling Constants / 7
2 AN OVERVIEW OF FLUORINE NMR 9
2.1. Introduction / 9
2.2. Fluorine Chemical Shifts / 10
2.2.1. Some Aspects of Shielding/Deshielding Effects on Fluorine Chemical Shifts / 11
2.2.2. Solvent Effects on Fluorine Chemical Shifts / 15
2.2.3. Overall Summary of Fluorine Chemical Shift Ranges / 16
2.3. The Effect of Fluorine Substituents on Proton Chemical Shifts / 17
2.4. The Effect of Fluorine Substituents on Carbon Chemical Shifts / 18
2.5. The Effect of Fluorine Substituents on 31P Chemical Shifts / 19
2.6. The Effect of Fluorine Substituents on 15N Chemical Shifts / 20
2.7. Spin-Spin Coupling Constants to Fluorine / 23
2.7.1. Effect of Molecule Chirality on Coupling / 27
2.7.2. Through-Space Coupling / 29
2.7.3. Fluorine-Fluorine Coupling / 32
2.7.4. Coupling Between Fluorine and Hydrogen / 33
2.7.5. Coupling Between Fluorine and Carbon / 35
2.7.6. Coupling Between Fluorine and Phosphorous / 38
2.7.7. Coupling Between Fluorine and Nitrogen / 39
2.8. Second-Order Spectra / 40
2.9. Isotope Effects on Chemical Shifts / 45
2.10. Advanced Topics / 48
2.10.1. Multidimensional 19F NMR / 50
3 THE SINGLE FLUORINE SUBSTITUENT 55
3.1. Introduction / 55
3.1.1. Chemical Shifts - General Considerations / 56
3.1.2. Spin-Spin Coupling Constants - General Considerations / 56
3.2. Saturated Hydrocarbons / 57
3.2.1. Primary Alkyl Fluorides / 57
3.2.2. Secondary Alkyl Fluorides / 61
3.2.3. Tertiary Alkyl Fluorides / 63
3.2.4. Cyclic and Bicyclic Alkyl Fluorides / 66
3.3. Influence of Substituents/Functional Groups / 70
3.3.1. Halogen Substitution / 70
3.3.2. Alcohol, Ether, Epoxide, Ester, Sulfide, Sulfone, Sulfonate, and Sulfonic Acid Groups / 77
3.3.3. Amino, Ammonium, Azide, and Nitro Groups / 80
3.3.4. Phosphorous Compounds / 83
3.3.5. Silanes, Stannanes, and Germanes / 83
3.4. Carbonyl Functional Groups / 84
3.4.1. Aldehydes and Ketones / 85
3.4.2. Carboxylic Acid Derivatives / 86
3.4.3. 1H and 13C NMR Data for Aldehydes, Ketones, and Esters / 86
3.4.4. ß-Ketoesters, Diesters, and Nitroesters / 89
3.5. Nitriles / 89
3.5.1. 1H and 13C NMR Data for Nitriles / 89
3.6. Alkenes with a Single Fluorine Substituent / 90
3.6.1. Hydrocarbon Alkenes / 90
3.6.2. Conjugated Alkenyl Systems / 93
3.6.3. Allylic Alcohols, Ethers, and Halides / 94
3.6.4. Halofluoroalkenes and Fluorovinyl Ethers / 97
