Organic structure determination using 2-D NMR spectroscopy: a problem-based approach
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Amsterdam [u.a.]
Elsevier, Acad. Press
2008
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis Klappentext |
| Physical Description: | XIV, 362 p. graph. Darst. |
| ISBN: | 9780120885220 |
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MARC
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| 100 | 1 | |a Simpson, Jeffrey H. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Organic structure determination using 2-D NMR spectroscopy |b a problem-based approach |c Jeffrey H. Simpson |
| 264 | 1 | |a Amsterdam [u.a.] |b Elsevier, Acad. Press |c 2008 | |
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Record in the Search Index
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| adam_text | Contents
Preface
хні
CHAPTER
1
Introduction
1.1
What Is Nuclear Magnetic Resonance?
1.2
Consequences of Nuclear Spin
1.3
Application of a Magnetic Field to a Nuclear Spin
1.4
Application of a Magnetic Field to an Ensemble of Nuclear Spins
1.5
Tipping the Net Magnetization Vertor from Equilibrium
1.6
Signal Detection
1.7
The Chemical Shift
1.8
The
l-D NMR
Spectrum
1.9
The 2-DNMR Spectrum
1.10
Information Content Available Using NMR
1
1
1
3
5
11
12
13
13
15
16
CHAPTER
2
Instrumental Considerations
2.1
Sample Preparation
2.1.1
NMR Tube Selection
2.1.2
Sample Purity
2.1.3
Solvent Selection
2.1.4
Cleaning NMR Tubes Prior to Use or Reuse
2.1.5
Drying NMR Tubes
2.1.6
Sample Mixing
2.1.7
Sample Volume
2.1.8
Solute Concentration
2.1.9
Optimal Solute Concentration
2.1.10
Minimizing Sample Degradation
2.2
Locking
2.3
Shimming
2.4
Temperature Regulation
2.5
Modern NMR Instrument Architecture
2.5.1
Generation of RF and Its Delivery to the NMR Probe
2.5
Λ
Probe Tuning
2S3 When to Tune the NMR Probe and Calibrate RF Pulses
2.5.4
RF Filtering
2.6
Pulse Calibration
2.7
Sample Excitation and the Rotating Frame of Reference
19
19
20
20
21
21
21
22
22
24
26
27
27
28
29
29
31
31
32
33
34
36
vii
viii Contents
2Л
Pulse Roll-off
2.9
Probe Variations
2.9.1
Small Volume NMR Probes
2.9.2
Flow-Through NMR Probes
2.9.3
Cryogenically Cooled Probes
2.9.4
Probe Sizes (Diameter of Recommended NMR Tube)
2.9.5
Normal Versus Inverse Coil Configurations in NMR Probes
2.10
Analog Signal Detection
2.11
Signal Digitization
37
39
41
41
42
43
44
45
45
CHAPTER
3
Data Collection, Processing, and Plotting
3.1
Setting the Spectral Window
3.2
Determining the Optimal Wait Between Scans
3.3
Setting the Acquisition Time
ЗЛ
How Many Points to Acquire in a 1-D Spectrum
3.5
Zero Filling and Digital Resolution
3.6
Setting the Number of Points to Acquire in a 2-D Spectrum
3.7
Truncation Error and Apodization
3.8
The Relationship Between T2
*
and Observed Line Width
3.9
Resolution Enhancement
3.10
Forward Linear Prediction
3.11
Pulse Ringdown and Backward Linear Prediction
3.12
Phase Correction
3.13
Baseline Correction
3.14
Integration
3.15
Measurement of Chemical Shifts and J-Couplings
3.16
Data Representation
51
51
53
56
57
58
59
61
62
64
65
66
67
70
71
73
76
CHAPTER
4
Ή
and 13C Chemical Shifts
4.1
The Nature of the Chemical Shift
4.2
Aliphatic Hydrocarbons
4.3
Saturated, Cyclic Hydrocarbons
4.4
Olefinic Hydrocarbons
4.5
Acetylenie
Hydrocarbons
4.6
Aromatic Hydrocarbons
4.7
Heteroatom
Effects
83
83
86
88
88
90
90
91
CHAPTER
5
Symmetry and Topicity
5.1
Homotopicity
5.2
Enantiotopicity
5.3
Diastereotopicity
95
95
97
98
Contents ix
5.4 Chemical
Equivalence
5.5
Magnetic
Equivalence
CHAPTER
б
Through-Bond Effects: Spin-Spin
(J)
Coupling
6.1
Origin of J-Coupling
6.2
Skewing of the Intensity of
Multiplets
6.3
Prediction of First-Order
Multiplets
6.4
The Karplus Relationship for Spins Separated by Three Bonds
6.5
The Karplus Relationship for Spins Separated by Two Bonds
6.6
Long Range J-Coupling
6.7
Decoupling Methods
6.8
One-Dimensional Experiments Utilizing J-Couplings
6.9
Two-Dimensional Experiments Utilizing J-Couplings
6.9.1
Homonudear Two-Dimensional Experiments Utilizing
J-Couplings
6.9.1.1
COSY
6.9.1.1.1
Phase Sensitive COSY
6.9.1.1.2
Absolute-Value COSY, Including gCOSY
6.9.1.2
TOCSY
6.9.1.3
INADEQUATE
6.9.2
Heteronuclear Two-Dimensional Experiments Utilizing J-Couplings
6.9.2.1
HMQC and HSQC
6.9.2.2
HMBC
99
99
101
101
103
106
110
111
113
113
115
117
118
118
119
120
120
123
124
124
132
CHAPTER
7
Through-Space Effects: The Nuclear Overhauser Effect
(NOE)
7.1
The Dipolar Relaxation Pathway
7
Λ
The Energetics of an Isolated Heteronuclear Two-Spin System
7.3
The Spectral Density Function
7.4
Decoupling One of the Spins in a Heteronuclear Two-Spin System
7.5
Rapid Relaxation via the Double Quantum Pathway
7.6
A One-Dimensional Experiment Utilizing the
NOE
7.7
Two-Dimensional Experiments Utilizing the
NOE
7.7.1
NOESY
7.7.2
ROESY
137
137
138
139
141
142
144
147
147
148
CHAPTER
8
Molecular Dynamics
8.1
Relaxation
8.2
Rapid Chemical Exchange
8.3
Slow Chemical Exchange
8.4
Intermediate Chemical Exchange
8.5
Two-Dimensional Experiments that Show Exchange
151
152
153
153
154
156
χ
Contents
CHAPTER
9
Strategies for Assigning Resonance to Atoms Within a Molecule
9.1
Prediction of Chemical Shifts
9.2
Prediction of Integrals and Intensities
9.3
Prediction of lH
Multiplets
9.4
Good Bookkeeping Practices
9.5
Assigning
Ή
Resonances on the Basis of Chemical Shifts
9.6
Assigning !H Resonances on the Basis of Multiplicities
9.7
Assigning
Ή
Resonances on the Basis of the gCOSY Spectrum
9Λ
The Best Way to Read a gCOSY Spectrum
9.9
Assigning 13C Resonances on the Basis of Chemical Shifts
9.10
Pairing
Ή
and 13C Shifts by Using the HSQC/HMQC Spectrum
9.11
Assignment of Nonprotonated 13C s on the Basis of the HMBC Spectrum
CHAPTER
10
Strategies for Elucidating Unknown Molecular Structures
10.1
Initial Inspection of the One-Dimensional Spectra
10.2
Good Accounting Practices
103
Identification of Entry Points
10.4
Completion of Assignments
CHAPTER
11
Simple Assignment Problems
11.1
2-Acetylbutyrolactone in CDCI3 (Sample
26)
11.2 .
α
-Terpinene
in
CDĄ
(Sample
28)
11.3
[lR)-endo-{+)-¥endiy Alcohol in CDCL, (Sample
30)
11.4 ( -
)-Bornyl Acetate in CDClj (Sample
31 )
11.5
N-Acetylhomocysteine Thiolactone in CDCI3 (Sample
35)
11.6
Guaiazulene in CDCI3 (Sample
52)
11.7
г-Нуагоху-З-Ріпапопе
in CDCI3 (Sample
76)
11.8
(R)-(+)-Perillyl Alcohol in CDCI3 (Sample
81)
11.9
y-Methoxy-^Methylcoumarin in
СОСІз
(Sample
90)
11.10
Sucrose in D2O (Sample
21)
CHAPTER
12
Complex Assignment Problems
12.1
Longifolene in CDCI3 (Sample
48)
12 .2 (+
)-Limonene in CDC^ (Sample
49)
12.3
i-Cinchodine in CDCb (Sample
53)
12.4
(SaRH+J-Sdareolide in CDC13 (Sample
54)
12.5 (—
i-Epicatechin in Acetone^ (Sample
55)
12.6
(-)-Eburnamonine in CDCI3 (Sample
71)
12.7
irons-Myrtanol in CDCI3 (Sample
72/78)
12.8
ris-Myrtanol in CDC13 (Sample
73/77)
12.9
Naringenin in Acetone-dg (Sample
89)
12.10
(-)-Ambroxide in CDCI3 (Sample Ambroxide)
157
158
159
159
160
162
163
166
169
171
173
178
183
184
187
191
191
199
199
201
205
209
214
217
221
224
227
230
233
233
238
241
246
251
255
258
261
264
268
Contents xi
CHAPTER
13
Simple Unknown Problems
13.1
Unknown
13.1
in CDC^ (Sample
20)
13.2
Unknown
13.2
in
CDĄ
(Sample
41)
13.3
Unknown
13.3
in CDClj (Sample
22)
13.4
Unknown
13.4
in CDClj (Sample
24)
13.5
Unknown
13.5
in CDClj (Sample
34)
13.6
Unknown
13.6
in CDC^ (Sample
36)
13.7
Unknown
13.7
in CDC^ (Sample
50)
13.8
Unknown
13.8
in CDC^ (Sample
83)
13.9
Unknown
13.9
in CDC^ (Sample
82)
13.10
Unknown
13.10
in CDC^ (Sample
84)
CHAPTER
14
Complex Unknown Problems
14.1
Unknown
14.1
in CDClj (Sample
32)
14.2
Unknown
14.2
in CDC^ (Sample
33)
14.3
Unknown
14.3
in CDClj (Sample
51)
14.4
Unknown
14.4
in CDC^ (Sample
74)
14.5
Unknown
14.5
in CDC^ (Sample
75)
14.6
Unknown
14.6
in CDC^ (Sample
80)
14.7
Unknown
14.7
in ACETONE-dj, (Sample
86)
14.8
Unknown
14.8
in CDClj (Sample
87)
14.9
Unknown
14.9
in CDClj (Sample
88)
14.10
Unknown
14.10
in CDClj (Sample
72)
Glossary of Terms
Index
271
271
274
278
280
282
285
287
290
293
295
299
299
302
305
309
312
315
319
322
326
329
333
349
Ideai
for advanced undergraduate and graduate courses in organic
spectroscopy, this book provides the analytical skills and methodologies
needed to assign nuclear magnetic resonances to known and unknown
molecular structures. Part I covers the essential knowledge
—
along wttn worked
examples—synthetic organic chemists should possess to understand and
apply NMR in their research. Part II presents a comprehensive selection of
40
problems
(20
knowns and
20
unknowns), consisting of !H and 13G 1-D spectra
plus muffiple 2-D spectra.
While most books on the subject focus on mathematically rigorous treatments, this
text balances rigor with guidance, providing novice and experienced chemists with
the tools needed to understand and interpret
2-0
NMR spectra.
•
Optimizes workflow by presenting strategies for assigning resonances
to known structures and for deducing structures of unknown organic
molecules based on their NMR spectra
•
improves
anaiyöca!
and interpretation skills through the use
of extensive examples and problem-solving techniques
•
Enhances understanding through detailed explanations of key
concepts, including an extensive glossary
|
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| id | DE-604.BV025552911 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T22:36:21Z |
| institution | BVB |
| isbn | 9780120885220 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-020153081 |
| oclc_num | 705354836 |
| open_access_boolean | |
| owner | DE-11 DE-355 DE-BY-UBR |
| owner_facet | DE-11 DE-355 DE-BY-UBR |
| physical | XIV, 362 p. graph. Darst. |
| publishDate | 2008 |
| publishDateSearch | 2008 |
| publishDateSort | 2008 |
| publisher | Elsevier, Acad. Press |
| record_format | marc |
| spelling | Simpson, Jeffrey H. Verfasser aut Organic structure determination using 2-D NMR spectroscopy a problem-based approach Jeffrey H. Simpson Amsterdam [u.a.] Elsevier, Acad. Press 2008 XIV, 362 p. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Strukturaufklärung (DE-588)4183788-5 gnd rswk-swf Zweidimensionale NMR-Spektroskopie (DE-588)4191219-6 gnd rswk-swf Organische Verbindungen (DE-588)4043816-8 s Strukturaufklärung (DE-588)4183788-5 s Zweidimensionale NMR-Spektroskopie (DE-588)4191219-6 s DE-604 Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020153081&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020153081&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Simpson, Jeffrey H. Organic structure determination using 2-D NMR spectroscopy a problem-based approach Organische Verbindungen (DE-588)4043816-8 gnd Strukturaufklärung (DE-588)4183788-5 gnd Zweidimensionale NMR-Spektroskopie (DE-588)4191219-6 gnd |
| subject_GND | (DE-588)4043816-8 (DE-588)4183788-5 (DE-588)4191219-6 |
| title | Organic structure determination using 2-D NMR spectroscopy a problem-based approach |
| title_auth | Organic structure determination using 2-D NMR spectroscopy a problem-based approach |
| title_exact_search | Organic structure determination using 2-D NMR spectroscopy a problem-based approach |
| title_full | Organic structure determination using 2-D NMR spectroscopy a problem-based approach Jeffrey H. Simpson |
| title_fullStr | Organic structure determination using 2-D NMR spectroscopy a problem-based approach Jeffrey H. Simpson |
| title_full_unstemmed | Organic structure determination using 2-D NMR spectroscopy a problem-based approach Jeffrey H. Simpson |
| title_short | Organic structure determination using 2-D NMR spectroscopy |
| title_sort | organic structure determination using 2 d nmr spectroscopy a problem based approach |
| title_sub | a problem-based approach |
| topic | Organische Verbindungen (DE-588)4043816-8 gnd Strukturaufklärung (DE-588)4183788-5 gnd Zweidimensionale NMR-Spektroskopie (DE-588)4191219-6 gnd |
| topic_facet | Organische Verbindungen Strukturaufklärung Zweidimensionale NMR-Spektroskopie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020153081&sequence=000003&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=020153081&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
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