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Organic Structure Determination Using 2-D NMR Spectroscopy - 1st Edition - ISBN: 9780120885220, 9780080916637

Organic Structure Determination Using 2-D NMR Spectroscopy

1st Edition

A Problem-Based Approach

Authors: Jeffrey Simpson Jeffrey Simpson
eBook ISBN: 9780080916637
Imprint: Academic Press
Published Date: 10th July 2008
Page Count: 384
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Description

Organic Structure Determination Using 2-D NMR Spectroscopy is a primary text for a course in NMR techniques, with the goal to learn to identify organic molecular structure. It presents strategies for assigning resonances to known structures and for deducing structures of unknown organic molecules based on their NMR spectra.

It contains 20 known and 20 unknown structure determination problems and features a supporting website from which instructors can download the structures of the unknowns in selected chapters, digital versions of all figures, and raw data sets for processing. Many other books describe the methods used, but none offer a large number of problems. Instructors at universities and colleges are forced to cobble together problems from a wide range of sources. The fragmentary approach to assembling course materials has a negative impact on course continuity and thus adversely impacts student retention.

This book will stand as a single source to which instructors and students can go to obtain a comprehensive compendium of NMR problems of varying difficulty.

Key Features

• Presents strategies for assigning resonances to known structures and for deducing structures of unknown organic molecules based on their NMR spectra
• Contains 20 known and 20 unknown structure determination problems

Readership

This is a primary text for a course in NMR techniques, with the goal to learn to identify organic molecular structure.

Table of Contents

PART I: Background and Methods

Chapter 1: Introduction
What is NMR?
Consequences of Nuclear Spin
Application of a Magnetic Field to a Single Nuclear Spin
Application of a Magnetic Field to an Ensemble of Nuclear Spins
Tipping the Net Magnetization Vector from Equilibrium
Signal Detection
The Chemical Shift
The 1-D NMR Spectrum
The 2-D NMR Spectrum
Information Content Available Using NMR

Chapter 2: Instrumental Considerations
Sample Preparation
Locking
Shimming
Temperature Regulation
Modern NMR Instrument Architecture
Pulse Calibration
Sample Excitation and the Rotating Frame of Reference
Pulse Rolloff
Probe Variations
Analog Signal Detection
Signal Digitization

Chapter 3: Data Collection, Processing, and Plotting
Setting the Spectral Window
Determining the Optimal Wait Between Scans
Setting the Acquisition Time
How Many Points to Acquire in a 1-D Spectrum
Zero Filling and Digital Resolution
Setting the Number of Points to Acquire in a 2-D Spectrum
Truncation Error and Apodization
The Relationship Between T2* and Observed Line Width
Resolution Enhancement
Forward Linear Prediction
Pulse Ringdown and Backward Linear Prediction
Phase Correction
Baseline Correction
Integration
Measurement of Chemical Shifts and J-Couplings
Data Representation

Chapter 4: 1H and 13C Chemical Shifts
The Nature of the Chemical Shift
Aliphatic Hydrocarbons
Saturated, Cyclic Hydrocarbons
Olefinic Hydrocarbons
Acetylenic Hydrocarbons
Aromatic Hydrocarbons
Heteroatom Effects

Chapter 5: Symmetry and Topicity
Homotopicity
Enantiotopicity
Diastereotopicity
Chemical Equivalence
Magnetic Equivalence

Chapter 6: Through-Bond Effects: Spin-Spin (J) Coupling
Origin of J-Coupling
Skewing of the Intensity of Multiplets
Prediction of First-Order Multiplets
The Karplus Relationship for Spins Separated by Three Bonds
The Karplus Relationship for Spins Separated by Two Bonds
Long Range J-Coupling
Decoupling Methods
One-Dimensional Experiments Utilizing J-Couplings
Two-Dimensional Experiments Utilizing J-Couplings

Chapter 7: Through-Space Effects: the Nuclear Overhauser Effect (NOE)
The Dipolar Relaxation Pathway
The Energetics of an Isolated Heteronuclear Two-Spin System
The Spectral Density Function
Decoupling One of the Spins in a Heteronuclear Two-Spin System
Rapid Relaxation via the Double Quantum Pathway
A One-Dimensional Experiment Utilizing the NOE
Two-Dimensional Experiments Utilizing the NOE

Chapter 8: Molecular Dynamics
Relaxation
Rapid Chemical Exchange
Slow Chemical Exchange
Intermediate Chemical Exchange
Two-Dimensional Experiments that Show Exchange

Chapter 9: Strategies for Assigning Molecules
Prediction of Chemical Shifts
Prediction of Integrals and Intensities
Prediction of 1H Multiplets
Good Bookkeeping Practices
Assigning 1H Resonances on the Basis of Chemical Shifts
Assigning 1H Resonances on the Basis of Multiplicities
Assigning 1H Resonances on the Basis of the gCOSY Spectrum
The Best Way to Read a 2-D gCOSY Spectrum
Assigning 13C Resonances on the Basis of Chemical Shifts
Pairing 1H and 13C Shifts By Using the HSQC/HMQC Spectrum
Assignment of Non-Protonated 13C’s on the Basis of the HMBC Spectrum

Chapter 10: Strategies for Elucidating Unknown Molecular Structures
Initial Inspection of the One-Dimensional Spectra
Good Accounting Practices
Identification of Entry Points
Completion of Assignments

PART II: Problems

Chapter 11 Simple Assignment Problems

Chapter 12: Complex Assignment Problems

Chapter 13: Simple Unknown Problems

Chapter 14: Complex Unknown Problems

Details

No. of pages:
384
Language:
English
Copyright:
© Academic Press 2008
Published:
10th July 2008
Imprint:
Academic Press
eBook ISBN:
9780080916637

About the Authors

Jeffrey Simpson

Jeffrey H Simpson, PhD, was Director of the Instrumentation Facility in the Department of Chemistry at M.I.T. from 2006 to 2017. Dr. Simpson’s career in NMR/instrumentation research and instruction spans 20 years, and he has authored an introductory text on the subject of NMR as well as publishing a number of peer-reviewed articles. He is one of the Founding Members of the New England NMR Society and served as VP from its inception to 2017. He currently is a faculty member in the Department of Chemistry at the University of Richmond.

Affiliations and Expertise

Department of Chemistry, University of Richmond, USA

Jeffrey Simpson

Affiliations and Expertise

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, USA

Reviews

"I like [the book] a lot. Books that cover theory in depth AND lots of problems are (surprisingly) rare."--Steven M. Graham, St. John's University

"The abundance of problems and highly detailed glossary are especially noteworthy; the quality of the spectrum presentations is excellent [...] Overall organization works well, and the layout and other 'production values' are what one has long come to expect from [Academic Press]."--Barry Shapiro

"When trying to explain two-dimensional nuclear magnetic resonance (NMR) spectroscopy, one may strive to avoid two pitfalls: getting bogged down in the mathematics behind the technique, or skipping the mathematics altogether and by default making the technique a "magic box." In his book, Simpson (MIT) has nearly done the impossible, covering two-dimensional NMR without slipping into either of those problems. Starting off with the instrumental setups and working through topics such as pulse sequences and spectral interpretation, this book gives readers all that they will need to prepare, run, and interpret a 2-D NMR experiment. This work would be useful for anyone who is currently using 2-D NMR and is a must for newcomers to the technique. Simpson provides almost 100 spectra to interpret as exercises, which make this volume an ideal teaching tool for 2-D NMR spectroscopy. Summing Up: Essential. Upper-division undergraduate through professional collections."-- S. S. Mason, Mount Union College writing CHOICE April 2009

 

Ratings and Reviews