Organic structure analysis

Abstract

CHAPTER 1.USING SPECTROSCOPIC DATA IN ORGANIC STRUCTURE ANALYSIS 1.1 A Glimpse of the Methods in Common Use 1.2 Characteristics of the Methods in Common Use 1.3 Steps in Establishing a Molecular Structure 1.4 Molecular Formula (MF) and Unsaturation Number (UN) 1.5 Substructures, Working Structures, and Final Structures 1.6 Limitations of Spectroscopic Data in Structure Analysis CHAPTER 2. INTRODUCTION TO NUCLEAR MAGNETIC RESONANCE 2.1 A Glimpse of the NMR Phenomenon 2.2 Commonly Studied Nuclei 2.3 Obtaining an NMR Spectrum 2.4 Magnetic Shielding 2.5 Relaxation Effects 2.6 Effect of Relaxation and NOE on Peak Intensities 2.7 Electric Quadrupole Effects 2.8 Measurement and Presentation of Data 2.9 Sample Preparation and Sample Size 2.10 Common Impurities in NMR Spectra 2.11 Other Useful Nuclei CHAPTER 3. INTERPRETATION AND USE OF PROTON AND CARBON CHEMICAL SHIFTS 3.1 A Glimpse of Chemical Shifts and Peak Areas 3.2 Terms and Conventions 3.3 Factors That Determine Chemical Shifts 3.4 Chemical Shift Positions of 'H/'3C Attached to Common Functional Groups 3.5 Chemical Shift Equivalence 3.6 Characteristic Chemical Shifts for Different Protons and Carbons 3.7 Using Databases to Estimate '3C NMR Chemical Shifts 3.8 Making Configurational Assignments Based on Chemical Shifts: Case Examples CHAPTER 4. INTERPRETATION AND USE OF PROTON AND CARBON COUPLING CONSTANTS 4.1 A Glimpse of Coupling Constants 4.2 First-Order Spectra and the n + 1 Rule 4.3 Terms and Conventions 4.4 Common Coupled Spin Systems 4.5 Magnetic Nonequivalence 4.6 Using Coupling Constants to Understand the Appearance of Spectra and Make Assignments 4.7 Coupling Constant Values for Different Carbon and Proton Types 4.8 Using Coupling Constants to Make Configurational Assignments 4.9 Ways to Simplify or Eliminate Coupling Effects 4.10 The Nuclear Overhauser effect 4.11 Additional Ways to Obtain J Values CHAPTER 5. MULTIPLE-PULSE AND MULTIDIMENSIONAL NMR TECHNIQUES 5.1 A Glimpse of Multiple-Pulse NMR Methods 5.2 Elements of Multiple-Pulse NMR 5.3 One-Dimensional NMR Techniques 5.4 Two-Dimensional NMR Techniques 5.5 Using Two-Dimensional NMR in Assigning Spectra 5.6 Using Two-Dimensional NMR Data to Determine an Unknown Structure 5.7 Strategies for Using 2D NMR in Structure Determination 5.8 Use of NOESY and ROESY to Determine Relative Stereochemistry and Conformations 5.9 Specialized Pulse Sequences 5.10 Configurational Analysis Based on Coupling Constants: Experimental Measurement of .3 J[CH 5.11 Computer-Assisted Structure Elucidation 5.12 Future Prospects in Multidimensional NMR CHAPTER 6. MASS SPECTROMETRY: CORE TECHNIQUES AND IONIZATION PROCESSES 6.1 A Glimpse of Mass Spectrometry 6.2 Measurement, Presentation of Data, and Nomenclature 6.3 Isotopes, Atomic Composition, Molecular Formulas, and Ionic Mass: Low and High Resolution and Measurements 6.4 Different Ionization Techniques in Mass Spectrometry 6.5 Different Techniques for Analyzing Ions in Mass Spectrometry 6.6 Detectors in Mass Spectrometry 6.7 Hyphenated Mass Spectrometry 6.8 Tandem Mass Spectrometry 6.9 Future Prospects CHAPTER 7. MASS SPECTROMETRY ANALYSIS OF SMALL AND LARGE MOLECULES 7.1 A Glimpse of Molecular Ions Revisited 7.2 Small-Molecule Mass Spectral Analysis 7.3 Large-Molecule Mass Spectrometry 7.4 Future Prospects CHAPTER 8. FRAGMENTATION PROCESSES IN ELECTRON IONIZATION MASS SPECTROMETRY 8.1 A Glimpse of Fragmentation in Mass Spectrometry 8.2 Interpreting a Low Resolution Electron Ionization Mass Spectrum 8.3 Fragmentation Processes 8.4 Identification of Functionality from Fragmentation Processes 8.5 Schematic Approach for the Interpretation of an EIMS CHAPTER 9. INFRARED SPECTROSCOPY 9.1 A Glimpse of Infrared Spectroscopy 9.2 Measurement and Presentation of Data 9.3 The Fundamentals 9.4 Identifying Functional Groups 9.5 Interpreted Infrared Spectra 9.6 Use of Infrared Databases CHAPTER 10. OPTICAL AND CHIROPTICAL TECHNIQUES: ULTRAVIOLET SPECTROSCOPY 10.1 A Glimpse of Ultraviolet Spectroscopy 10.2 Measurement and Presentation of Data 10.3 The Fundamentals for Interpreting Spectra 10.4 Identifying Functional Groups 10.5 Theoretical Simulations of UV Spectra 10.6 The Behavior of Chiral Chromophores ORD/CD 10.7 The Exciton Chirality Method 10.8 Other Ways to Examine Chiral Chromophores CHAPTER 11. STRATEGIES OF DETERMINING STRUCTURE AND STEREOCHEMISTRY: SPECTROSCOPIC DATA TRANSLATED INTO STRUCTURES 11.1 A Glimpse of the Combined Use of Spectroscopic Data 11.2 The Strategies of Determining Structure and Stereochemistry 11.3 Dereplication Strategies 11.4 Worked Examples of Deriving Structures from Spectroscopic Data CHAPTER 12. PROBLEMS IN ORGANIC STRUCTURE ANALYSIS 12.1 A Glimpse of the Scope of the 51 Unknowns 12.2 Using the Spectra, Accompanying Information, and Other Resources APPENDICES A. COLLECTIONS OF SPECTRA OR DATA TABLES B. SHAPE OF MS CLUSTERS C. CAS REGISTRY NUMBERS FOR UNKNOWNS D. GLOSSARY AND ABBREVIATIONS