NMR SPECTROSCOPY. Basic Principles, Concepts, and Applications in Chemistry. Harald Günther University of Siegen, Siegen, Germany.

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1 NMR SPECTROSCOPY Basic Principles, Concepts, and Applications in Chemistry Harald Günther University of Siegen, Siegen, Germany Second Edition Translated by Harald Günther JOHN WILEY & SONS Chichester New York Brisbane Toronto Singapore

2 CONTENTS Preface Introduction xi xiii CHAPTER 1: The Physical Basis of the Nuclear Magnetic Resonance Experiment. Part The Quantum Mechanical Model for the Isolated Proton 1 2. The Experimental Demonstration of Quantized Angular Momentum and of the Resonance Equation 4 3. The Nuclear Magnetic Resonance Experiment on Compact Matter and the Principle of the Nuclear Magnetic Resonance Spectrometer The Magnetic Properties of Other Nuclei 10 CHAPTER 2: The Proton Magnetic Resonance Spectra of Organic Molecules The Chemical Shift Chemical Shift Measurements The Integration of the Spectrum The Dependence of the Resonance Frequency on Structure A General Survey Spin-Spin Coupling Simple Rules for the Interpretation of Multiplet Structures Spin-Spin Coupling with Other Nuclei The Limits of the Simple Splitting Rules Spin-Spin Decoupling The Structure Dependence of the Spin-Spin Coupling A General Survey References 52 CHAPTER 3: Experimental Aspects of Nuclear Magnetic Resonance Spectroscopy Sample Preparation and Sample Tubes Internal and External Standards; Solvent Effects Tuning the Spectrometer Increasing the Sensitivity 63

3 Vi CONTENTS 5. The Measurement of Spectra at Different Temperatures References 67 CHAPTER 4: Chemical Shift and Spin-Spin Coupling as Functions of Structure The Origins of Proton Chemical Shifts The Influence of the Electron Density at the Proton The Influence of the Electron Density at Neighbouring Carbon Atoms The Influence of Induced Magnetic Moments of Neighbouring Atoms and Bonds The Ring Current Effect in Cyclic Conjugated n Systems The Magnetic Anisotropy of the Cyclopropane Ring The Electric Field Effect of Polar Groups and the van der Waals Effect Chemical Shifts through Hydrogen Bonding Chemical Shifts of Protons in Organometallic Compounds Solvent Effects Empirical Substiruent Constants Tables of Proton Resonances in Organic Molecules Spin-Spin Coupling and Chemical Structure The Geminal Coupling Constant ( 2 J) The Vicinal Coupling Constant ( 3 J) Long-Range Coupling Constants (V, 5 J) Direct Spin-Spin Interaction and Through-Space Coupling Tables of Spin-Spin Coupling Constants in Organic Molecules References 133 CHAPTER 5: The Analysis of High-Resolution Nuclear Magnetic Resonance Spectra Notation for Spin Systems Quantum Mechanical Formalism The Schrödinger Equation The Hamiltonian Operator for High-Resolution Nuclear Magnetic Resonance Spectroscopy The Calculation of Individual Spin Systems The Stationary States of a Single Nucleus A Two Nuclei without Spin-Spin Interaction (J^ = 0); Selection Rules Two Nuclei with Spin-Spin Interaction (Ty ^ 0) The AB System The AX System and the First-Order Approximation General Rules for the Treatment of More Complex Spin Systems 157

4 CONTENTS VÜ 5. The Calculation of the Parameters v< and J tj from the Experimental Spectrum The Direct Analysis of the AB System Spin Systems with Three Nuclei Spin Systems with Four Nuclei Computer Analysis References 198 CHAPTER 6: The Influence of Molecular Symmetry and Chirality on Proton Magnetic Resonance Spectra Spectral Types and Structural Isomerism The Influence of Chirality on the NMR Spectrum The Analysis of Degenerate Spin Systems by Means of 13 C Satellites and H/D Substitution References 218 CHAPTER 7: The Physical Basis of the Nuclear Magnetic Resonance Experiment. Part II: Fourier Transform and Pulse Nuclear Magnetic Resonance Resonance for the Isolated Nucleus Resonance for a Macroscopic Sample and the CW NMR Signal Relaxation Effects Longitudinal Relaxation Transverse Relaxation Pulse Spectroscopy T\ Measurements The Spin Echo Experiment Pulse Fourier Transform (FT) Spectroscopy Experimental Aspects of Pulse Fourier Transform Spectroscopy The FT NMR Spectrometer Basic Principles and Operation Excitation and Detection Complications with FT NMR Spectroscopy Data Improvement Double Resonance Experiments Homonuclear Spin Decoupling Heteronuclear Double Resonance Broadband Decoupling Double Resonance Experiments for Spectral Analysis References 271 CHAPTER 8: Two-Dimensional Nuclear Magnetic Resonance Spectroscopy The Principles of Two-Dimensional NMR Spectroscopy Graphical Presentation of Two-Dimensional NMR Spectra 277

5 VÜi CONTENTS 2. The Spin Echo Experiment in Modern NMR Spectroscopy The Time-Dependence of Transverse Magnetization Chemical Shifts and Spin-Spin Coupling Constants and the Spin Echo Experiment Two-Dimensional Spin Echo Spectroscopy: The Separation of Parameters S and J Applications of Homonuclear *H,/,<5-Spectroscopy Practical Aspects of./,<5-spectroscopy The COSY Experiment Two-Dimensional 'H/H Shift Correlations Some Experimental Aspects of 2D-COSY Spectroscopy Artefacts in COSY Spectra Modifications of the Jeener Pulse Sequence The Product Operator Formalism The Phenomenon of Coherence The Operator Basis for an AX System Zero and Multiple Quantum Coherences The Evolution of Operators The Observables The COSY Experiment within the Product Operator Formalism The COSY Experiment with Double Quantum Filter (COSY-DQF) Phase Cycles Gradient Enhanced Spectroscopy Universal Building Blocks for Pulse Sequences Constant Time Experiments: coi-decoupled COSY Bird Pulses Low-Pass Filter z-filter Homonuclear Shift Correlation by Double Quantum Selection of AX Systems The 2D INADEQUATE Experiment Three-Dimensional NMR Experiments References 333 CHAPTER 9: The Influence of Dynamic Effects on *H Nuclear Magnetic Resonance Spectra The Exchange of Protons between Positions with Different Larmor Frequencies The Quantitative Description of Dynamic Nuclear Magnetic Resonance Relationships to Reaction Kinetics Approximate Solutions and Sources of Error More Complex Exchange Phenomena Application of Double Resonance Experiments to the Determination of Rate Constants 346

6 CONTENTS IX 1.6 Two-Dimensional Exchange Spectroscopy (EXSY) Measurements of First Order Rate Constants by Integration The Internal Dynamics of Organic Molecules Hindrance to Internal Rotation Inversion of Configuration Ring Inversion Valence Tautomerism Dynamic Processes in Organometallic Compounds and Carbocations Intermolecular Exchange Processes The Influence of 14 N Nuclei on Proton Resonances References 388 CHAPTER 10: Selected Experimental Techniques of Nuclear Magnetic Resonance Spectroscopy Superconducting Magnets The Nuclear Overhauser Effect (NOE) One-Dimensional NOE Experiments Complications During NOE Measurements NOE Difference Spectroscopy Two-Dimensional Nuclear Overhauser Spectroscopy (NOESY) Polarization Transfer Experiments The SPI Experiment The INEPT-Pulse Sequence Rotating Frame Experiments Spinlock and Hartmann-Hahn Condition Spinlock Experiments in Solution Chemically Induced Dynamic Nuclear Polarization (CIDNP) Energy Polarization (Net Effect) Entropy Polarization (Multiplet Effect) The Kaptein Rules Nuclear Magnetic Resonance Spectroscopy of Paramagnetic Materials Contact Shifts Pseudocontact Shifts Shift Reagents Nuclear Magnetic Resonance of Partially Oriented Molecules High-Resolution Solid State Nuclear Magnetic Resonance Spectroscopy The Experimental Techniques of High-Resolution Solid State NMR Spectroscopy Applications of High-Resolution Solid State NMR Spectroscopy Nuclear Magnetic Resonance in Biology and Medicine 453

7 X CONTENTS 9.1 In-vivo NMR Spectroscopy NMR Imaging References 460 CHAPTER 11: Carbon-13 Nuclear Magnetic Resonance Spectroscopy Historical Development and Most Important Areas of Application Experimental Aspects of Carbon-13 Nuclear Magnetic Resonance Spectroscopy Gated Decoupling Assignment Techniques Chemical Shifts Theoretical Models Empirical Correlations Carbon-13 Spin-Spin Coupling Constants Carbon-13 Coupling Constants and Chemical Structure Carbon-13 Spin-Lattice Relaxation Rates References 512 CHAPTER 12: Appendix The 'Ring Current Effect' of the Benzene Nucleus Tables of Proton Resonance Frequencies and 'H^H Coupling Constants The Hamiltonian Operator (5.3) in Polar Coordinates Commutable Operators The F z Operator Eigenfunctions of the AB 2 System Equations for the Direct Analysis of AA'BB' Systems The Bloch Equations The Bloch Equations Modined for Chemical Exchange The Haigh Notation for Spin Systems Chemical Shifts of 13 C Resonances in Organic Compounds The International System (SI) of Units (MKSA System) References Standard Definitions of Terms, Symbols, Conventions, and References Relating to High-Resolution Nuclear Magnetic Resonance (NMR) Spectroscopy 540 BIBLIOGRAPHY 549 SOLUTIONS TO EXERCISES 555 INDEX 567

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