Nmr Data Interpretation Explained - Understanding 1d 2d Nmr Spectra of Organic Compounds Natural

Through numerous examples, the principles of the relationship between chemical structure and the NMR spectrum are developed in a logical, step-by-step fashion
* Includes examples and exercises based on real NMR data including full 600 MHz one- and two-dimensional datasets of sugars, peptides, steroids and natural products
* Includes detailed solutions and explanations in the text for the numerous examples and problems and also provides large, very detailed and annotated sets of NMR data for use in understanding the material
* Describes both simple aspects of solution-state NMR of small molecules as well as more complex topics not usually covered in NMR books such as complex splitting patterns, weak long-range couplings, spreadsheet analysis of strong coupling patterns and resonance structure analysis for prediction of chemical shifts
* Advanced topics include all of the common two-dimensional experiments (COSY, ROESY, NOESY, TOCSY, HSQC, HMBC) covered strictly from the point of view of data interpretation, along with tips for parameter settings

Inhaltsverzeichnis

Examples xi
 
Preface xiii
 
Acknowledgments xv
 
About the Companion Website xvii
 
Chapter 1 | Spectroscopy and the Proton NMR Experiment 1
 
1 What is the Structure of a Molecule? 1
 
2 Mass Spectrometry 3
 
2.1 Ionization Methods and Molecular Ions 4
 
2.1.1 Electron Impact (EI) 4
 
2.1.2 Soft Ionization 5
 
2.2 High-Resolution Mass Spectrometry and Exact Mass 5
 
2.3 Isotope Patterns and the Halogens Br and Cl 7
 
3 Infrared (IR) Spectroscopy 9
 
4 Ultraviolet (UV) and Visible Spectroscopy 10
 
5 A Highly Simplified View of the NMR Experiment 13
 
Chapter 2 | Chemical Shifts and Splitting Patterns 17
 
1 Chemical Shifts in the Proton Spectrum 17
 
2 Splitting: The Effect of One Neighbor: A Doublet 21
 
3 Splitting: The Effect of Two Neighbors: A Triplet 23
 
4 Splitting: The Effect of Three Neighbors: A Quartet 25
 
5 Splitting: The Effect of "n" Neighbors: A Multiplet 30
 
6 Using Splitting Patterns to Choose from a Group of Isomers 34
 
7 Peak Intensities (Peak Areas) and the Number of Protons in a Peak 37
 
8 Publication Format for Proton NMR Data 39
 
9 Recognizing Common Structure Fragments 41
 
10 Overlap in Proton NMR Spectra. Example: 1-Methoxyhexane 45
 
11 Protons Bound to Oxygen: OH Groups. Example: 2-Ethyl-1-Butanol 48
 
12 Summary of Chemical Shifts and Splitting Patterns 50
 
Chapter 3 | Proton ( 1H) NMR of Aromatic Compounds 51
 
1 Benzene: The Aromatic Ring Current and the Shielding Cone 51
 
2 Monsubstituted Benzene: X-C6H5 52
 
2.1 Toluene 52
 
2.2 Aromatic Chemical Shifts: Resonance Structures 54
 
2.3 Nitrobenzene 55
 
2.4 Anisole 56
 
2.5 Substituent Effects on Aromatic Chemical Shifts 58
 
2.6 Long-Range J Couplings in Aromatic Rings: Protons 4 Bonds Apart 59
 
3 Disubstituted Benzene: X-C6H4-Y 62
 
3.1 Symmetrical Disubstituted Benzene: X-C6H4-X 62
 
3.2 Unsymmetrical Disubstituted Benzene, X-C6H4-Y 72
 
3.2.1 para (1,4) Disubstituted Benzene: p-X-C6H4-Y 73
 
3.2.2 meta (1,3) Disubstituted Benzene: m-X-C6H4-Y 78
 
3.2.3 ortho (1,2) Disubstituted Benzene: o-X-C6H4-Y 87
 
4 Coupling Between Aromatic Ring Protons and Substitutent Protons; Homonuclear Decoupling 100
 
4.1 The Methyl Group (CH3) 100
 
4.2 The Methoxy Substituent (OCH3) 102
 
4.3 The Formyl (H-C?O) Substituent 103
 
5 Trisubstituted Aromatic Rings: The AB2 System 106
 
6 Other Aromatic Ring Systems: Heteroaromatics, Five-Membered Rings and Fused Rings 110
 
6.1 Pyridine (C5H5N) 111
 
6.2 Pyrrole (C4H5N) 112
 
6.3 Furan (C4H4O) 113
 
6.4 Naphthalene (C10H8) 115
 
6.5 Indole (C8H7N) 117
 
6.6 Quinoline and Isoquinoline (C9H7N) 118
 
7 Summary of New Concepts: Proton NMR of Aromatic Compounds 120
 
Chapter 4 | Carbon-13 (13C) NMR 125
 
1 Natural Abundance and Sensitivity of 13C 125
 
2 Proton Decoupling--Removing the Splitting Effect of Nearby Protons 126
 
3 Intensity of 13C Peaks--Symmetry and Relaxation 126
 
4 Chemical Shifts of Carbon-13 (13C) Nuclei 129
 
4.1 13C Frequency and Chemical Shift Reference 129
 
4.2 General Regions of the 13C Chemical Shift Scale 130
 
4.3 Correlations between 1H and 13C Chemical Shift for a C-H Pair 132
 
4.4 Quantitation of the Steric Effect for 13C Chemical Shifts 135
 
4.5 Example of Steric Effects on 13C Chemical Shifts: The "Crowded CH" in Steroids 141
 
4.6 The gamma-gauche Effect: Steric

Über den Autor / die Autorin

Neil E. Jacobsen has been the NMR Facility Manager in the Department of Chemistry and Biochemistry at the University of Arizona for the last 20 years. He teaches an undergraduate course in NMR Spectroscopy (Organic Qualitative Analysis) using a series of unknowns including monoterpenes and steroids, with students acquiring their own 400 MHz 1D and 2D NMR data. He also teaches a graduate course in Organic Synthesis and NMR Spectroscopy that is focused on using the spectrometers and interpreting complex NMR data. He has 30 years of experience working in the field of NMR spectroscopy, and during that time he has authored 46 publications in peer-reviewed journals as well as the 2007 Wiley book NMR Spectroscopy Explained.

Zusammenfassung

Through numerous examples, the principles of the relationship between chemical structure and the NMR spectrum are developed in a logical, step-by-step fashion
* Includes examples and exercises based on real NMR data including full 600 MHz one- and two-dimensional datasets of sugars, peptides, steroids and natural products
* Includes detailed solutions and explanations in the text for the numerous examples and problems and also provides large, very detailed and annotated sets of NMR data for use in understanding the material
* Describes both simple aspects of solution-state NMR of small molecules as well as more complex topics not usually covered in NMR books such as complex splitting patterns, weak long-range couplings, spreadsheet analysis of strong coupling patterns and resonance structure analysis for prediction of chemical shifts
* Advanced topics include all of the common two-dimensional experiments (COSY, ROESY, NOESY, TOCSY, HSQC, HMBC) covered strictly from the point of view of data interpretation, along with tips for parameter settings

Produktdetails

• Autoren: Jacobsen, Ne Jacobsen, Neil E Jacobsen, Neil E. Jacobsen
• Verlag: Wiley, John and Sons Ltd
• Sprache: Englisch
• Produktform: Fester Einband
• Erschienen: 09.12.2016
• EAN: 9781118370223
• ISBN: 978-1-118-37022-3
• Seiten: 656
• Themen: Naturwissenschaften, Medizin, Informatik, Technik > Medizin > Klinische Fächer; Science, SCIENCE / Chemistry / Analytic, SCIENCE / Spectroscopy & Spectrum Analysis