NMR data interpretation explained: understanding 1D and 2D NMR spectra of organic compounds and natural products
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| 1. Verfasser: | |
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| Format: | Buch |
| Sprache: | English |
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Hoboken, New Jersey
Wiley
[2017]
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis Inhaltsverzeichnis |
| Beschreibung: | xvii, 629 Seiten Illustrationen, Diagramme (teilweise farbig) |
| ISBN: | 9781118370223 |
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Datensatz im Suchindex
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| adam_text | NMR DATA INTERPRETATION EXPLAINED
/ JACOBSEN, NEIL E.
: 2017
TABLE OF CONTENTS / INHALTSVERZEICHNIS
SPECTROSCOPY AND THE PROTON NMR EXPERIMENT
CHEMICAL SHIFTS AND SPLITTING PATTERNS
PROTON (1H) NMR OF AROMATIC COMPOUNDS
CARBON-13 (13C) NMR
ALKENES (OLEFINS)
CHIRALITY AND STEREOCHEMISTRY: NATURAL PRODUCTS
SELECTIVE PROTON EXPERIMENTS: BIOLOGICAL MOLECULES
HOMONUCLEAR TWO-DIMENSIONAL NMR: CORRELATION OF ONE HYDROGEN (1H) TO
ANOTHER
HETERONUCLEAR TWO-DIMENSIONAL NMR: CORRELATION OF ONE HYDROGEN (1H) TO
ONE CARBON (13C)
STRUCTURE ELUCIDATION USING 2D NMR.
DIESES SCHRIFTSTUECK WURDE MASCHINELL ERZEUGT.
Contents
Examples xi
Preface xiii
Acknowledgments xv
About the Companion Website xvii
Chapter 1 | Spectroscopy and the Proton NMR Experiment
1 What is the Structure of a Molecule? 1
2 Mass Spectrometry 3
2 1 Ionization Methods and Molecular Ions 4
211 Electron Impact (El) 4
212 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
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 CH) NMR of Aromatic Compounds
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
1
17
51
v
vi
CONTENTS
Chapter 4
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
321 para (1,4) Disubstituted Benzene: p-X-C6H4-Y 73
322 meta (1,3) Disubstituted Benzene: m-X-CöH4-Y 78
323 ortho (1,2) Disubstituted Benzene: o-X-C6H4-Y 87
4 Coupling Between Aromatic Ring Protons and Substitutent Protons; Homonudear
Decoupling 100
4 1 The Methyl Group (CH3) 100
4 2 The Methoxy Substituent (OCH3) 102
4 3 The Formyl (H-C=0) 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 (CÄO) 113
6 4 Naphthalene (Ci0H8) 115
6 5 Indole (C8H7N) 117
6 6 Quinoline and Isoquinoline (C9H7N) 118
7 Summary of New Concepts: Proton NMR of Aromatic Compounds 120
I Carbon-13 C3C) NMR 125
1 Natural Abundance and Sensitivity of ,3C 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 y-gauche Effect: Steric Shifts That Give Stereochemical Information 143
4 7 Inductive Effects in 13C Chemical Shifts: Electronegative Atoms 147
4 8 The Effect of Ring Strain on 13C Chemical Shift of sp3-Hybridized Carbons 150
5 Quaternary Carbons: the Carbonyl Group 151
6 Simple Aromatic Compounds: Substituent Effects on 13C Chemical Shifts 156
7 Highly Oxygenated Benzene Rings and Coumarin 161
8 Fused Rings and Heteroaromatic Compounds 165
8 1 Pyridine (C5H5N) 165
8 2 Pyrrole (C4H5N) 167
8 3 Furan (C4H40) 168
8 4 Naphthalene (Ci0H8) 168
8 5 Indole (C8H7N) 170
8 6 Quinoline and Isoquinoline (C9H7N) 173
9 Edited 13C Spectra: DEPT 174
9 1 Non-decoupled 13C Spectra 175
9 2 Edited 13C Spectra 176
9 3 Practical Details of the DEPT Experiment 181
931 Sensitivity 181
CONTENTS
Chapter 5
Chapter 6
Chapter 7
vil
932 Pulse Calibration 181
933J Value Setting 182
934 Phase Correction 185
10 The Effect of Other Magnetic Nuclei on the 13C Spectrum: 31P, 19Ff 2H and 14N 185
10 1 Splitting of 13C Peaks By Deuterium (2H) 185
10 2 Splitting of 13C Peaks by Phosphorus (31P) 186
10 3 Splitting of 13C Peaks by Fluorine (19F) 188
10 4 Splitting and Broadening of 13C Peaks by Nitrogen (14N) 189
11 Direct Observation of Nuclei Other Than Proton CH) and Carbon (13C) 190
11 1 Phosphorus-31 (31P) NMR 192
11 2 Fluorine-19 (19F) NMR 194
| Alkenes (Olefins) 198
1 Proton Chemical Shifts of Simple Olefins 199
2 Short-Range (Two and Three Bond) Coupling Constants (/ Values) in Olefins 202
3 The Allylic Coupling: A Long-Range (Four-Bond) J Coupling 205
4 Long-Range Olefin Couplings in Cholesterol: The b/s-Allylic Coupling (5J) 209
5 Carbon-13 Chemical Shifts of Hydrocarbon Olefins (Alkenes) 210
6 Resonance Effects on Olefinic 13C Chemical Shifts 214
7 Alkynes 225
| Chirality and Stereochemistry: Natural Products 227
1 The Molecules of Nature 227
2 Chirality, Chiral Centers, Chiral Molecules, and the Chiral Environment 230
3 The AB System 232
4 Detailed Analysis of the AB Spectrum: Calculating the Chemical Shifts 234
5 The ABX System 237
6 Variations on the ABX Theme: ABX3, ABX2 and ABXY 245
7 The Effect of Chirality on 13C Spectra Diastereotopic Carbons 249
8 A Closer Look at Chemical Shift Equivalence in an Asymmetric
Environment 251
8 1 Chemical Shift Equivalence of CH3 Group Protons 251
8 2 Non-Equivalence of CH2 Group Protons 252
8 3 Chemical Shift Equivalence by Symmetry 252
9 J Couplings and Chemical Shifts in the Rigid Cyclohexane Chair System 255
9 1 Cyclohexene and Cyclohexenone 262
10 A Detailed Look at the Dependence of 3jHH on Dihedral Angle: The Karplus
Relation 266
11 Magnetic Non-Equivalence The X-CH2-CH2-Y Spin System: A2B2 and AA BB Patterns 276
12 Bicydic Compounds and Small Rings (Three- and Four-Membered) 286
12 1 The Bicyclo[2 2 1] Ring System 286
12 2 The Bicyclo[3 1 0] Ring System 291
12 3 The Bicyclo[3 1 1] Ring System 294
Reference 298
| Selective Proton Experiments: Biological Molecules 299
1 Sugars: Monosaccharides and Oligosaccharides 299
2 Slowing of OH Exchange in Polar Aprotic Solvents Like DMSO 305
3 Selective TOCSY Applied to the Assignment of the ^ Spectra of Sugars 307
viii
CONTENTS
4 The Selective NOE (Nuclear Overhauser Effect) Experiment 319
4 1 Recognizing Artifacts in Selective NOE Spectra 320
4 2 The Relationship Between NOE Intensity and Distance 320
4 3 Magnetization Transfer in the Selective TOCSY and Selective
NOE Experiments 321
5 Amino Acids and Peptides 331
6 Nucleic Acids 348
7 Parameter Settings for NMR Experiment Setup and NMR Data Processing 357
Bibliography 358
Chapter 8 | Homonuclear Two-Dimensional NMR: Correlation of
One Hydrogen CH) to Another 359
1 Selective TOCSY Experiments Displayed as a Stacked Plot 359
2 The Two-Dimensional COSY Experiment 365
3 Shape and Fine Structure of COSY Crosspeaks; Contour Plots 370
4 2D-COSY Spectra of Sugars 376
5 2D-COSY Spectra of Aromatic Compounds 391
6 Parameter Settings in the 2D COSY Experiment; The DQF-COSY Experiment 397
7 COSY Spectra of Peptides 399
8 COSY Spectra of Natural Products 405
9 Two-Dimensional (2D) TOCSY (Total Correlation Spectroscopy) 412
10 Two-Dimensional (2D) NOESY (Nuclear Overhauser Effect Spectroscopy) 423
Parameter Settings Used for 2D Spectra in this Chapter 429
Chapter 9 | Heteronuclear Two-Dimensional NMR: Correlation of
One Hydrogen (JH) to One Carbon (13C) 430
1 3-Heptanone: A Thought Experiment 430
2 Edited HSQC: Making the CH2 Protons Stand Out 436
3 The 2D-HSQC Spectrum of Cholesterol 443
4 A Detailed Look at the HSQC Experiment 455
5 Parameters and Settings for the 2D-HSQC Experiment 458
5 1 Spectral Window 458
5 2 Acquisition Time 458
5 3 One-Bond J Coupling Value 459
5 4 Number of ID Spectra Acquired: F1 Resolution 460
5 5 Number of Scans: Sensitivity 460
6 Data Processing: Phase Correction in Two Dimensions 460
7 Long-Range Couplings between 123456789 10 11H and 13C 463
8 2D-HMBC (Heteronuclear Multiple-Bond Correlation) 465
8 1 2D-HMBC Spectra of Aromatic Compounds 467
8 2 HMBC Spectra of Natural Products: Using the Methyl Correlations 475
8 3 HMBC Spectra of Sugars 491
9 Parameters and Settings for the 2D-HMBC Experiment 495
9 1 Spectral Window 495
9 2 Acquisition Time 496
9 3 One-Bond and Long-Range JCh Coupling Values 496
9 4 Number of Scans 496
10 Comparison of HSQC and HMBC 496
11 HMBC Variants 497
CONTENTS
ix
Chapter 10
Index 617
Parameter Settings Used for 2D Spectra in this Chapter 497
References 498
| Structure Elucidation Using 2D NMR 499
1 Literature Structure Problems 500
2 Sesquiterpenoids 501
3 Steroids 522
4 Oligosaccharides 552
5 Alkaloids 574
6 Triterpenes 597
|
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| spelling | Jacobsen, Neil E. Verfasser aut NMR data interpretation explained understanding 1D and 2D NMR spectra of organic compounds and natural products Neil E. Jacobsen, Ph.D., University of Arizona Nuclear magnetic resonance data interpretation explained Hoboken, New Jersey Wiley [2017] © 2017 xvii, 629 Seiten Illustrationen, Diagramme (teilweise farbig) txt rdacontent n rdamedia nc rdacarrier Nuclear magnetic resonance spectroscopy Nuclear magnetic resonance Organic compounds Spectra Spectrum analysis NMR-Spektroskopie (DE-588)4075421-2 gnd rswk-swf Datenanalyse (DE-588)4123037-1 gnd rswk-swf NMR-Spektroskopie (DE-588)4075421-2 s Datenanalyse (DE-588)4123037-1 s b DE-604 LoC Fremddatenuebernahme application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029374139&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029374139&sequence=000003&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Jacobsen, Neil E. NMR data interpretation explained understanding 1D and 2D NMR spectra of organic compounds and natural products Nuclear magnetic resonance spectroscopy Nuclear magnetic resonance Organic compounds Spectra Spectrum analysis NMR-Spektroskopie (DE-588)4075421-2 gnd Datenanalyse (DE-588)4123037-1 gnd |
| subject_GND | (DE-588)4075421-2 (DE-588)4123037-1 |
| title | NMR data interpretation explained understanding 1D and 2D NMR spectra of organic compounds and natural products |
| title_alt | Nuclear magnetic resonance data interpretation explained |
| title_auth | NMR data interpretation explained understanding 1D and 2D NMR spectra of organic compounds and natural products |
| title_exact_search | NMR data interpretation explained understanding 1D and 2D NMR spectra of organic compounds and natural products |
| title_full | NMR data interpretation explained understanding 1D and 2D NMR spectra of organic compounds and natural products Neil E. Jacobsen, Ph.D., University of Arizona |
| title_fullStr | NMR data interpretation explained understanding 1D and 2D NMR spectra of organic compounds and natural products Neil E. Jacobsen, Ph.D., University of Arizona |
| title_full_unstemmed | NMR data interpretation explained understanding 1D and 2D NMR spectra of organic compounds and natural products Neil E. Jacobsen, Ph.D., University of Arizona |
| title_short | NMR data interpretation explained |
| title_sort | nmr data interpretation explained understanding 1d and 2d nmr spectra of organic compounds and natural products |
| title_sub | understanding 1D and 2D NMR spectra of organic compounds and natural products |
| topic | Nuclear magnetic resonance spectroscopy Nuclear magnetic resonance Organic compounds Spectra Spectrum analysis NMR-Spektroskopie (DE-588)4075421-2 gnd Datenanalyse (DE-588)4123037-1 gnd |
| topic_facet | Nuclear magnetic resonance spectroscopy Nuclear magnetic resonance Organic compounds Spectra Spectrum analysis NMR-Spektroskopie Datenanalyse |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029374139&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029374139&sequence=000003&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT jacobsenneile nmrdatainterpretationexplainedunderstanding1dand2dnmrspectraoforganiccompoundsandnaturalproducts AT jacobsenneile nuclearmagneticresonancedatainterpretationexplained |
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