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Cover

Organic Structure Analysis

Second Edition

Phillip Crews, Jaime Rodriguez, and Marcel Jaspars

Publication Date - October 2009

ISBN: 9780195336047

656 pages
Hardcover
8-1/2 x 11 inches

In Stock

Retail Price to Students: $214.99

The most up-to-date integrated spectroscopy text available, Organic Structure Analysis, Second Edition, is the only text that teaches students how to solve structures as they are solved in actual practice.

Description

The most up-to-date integrated spectroscopy text available, Organic Structure Analysis, Second Edition, is the only text that teaches students how to solve structures as they are solved in actual practice. Ideal for advanced undergraduate and graduate courses in organic structure analysis, organic structure identification, and organic spectroscopy, it emphasizes real applications--integrating theory as needed--and introduces students to the latest spectroscopic methods.

FEATURES
* Focus on Structure: Opens with structural elements and then considers the characteristics, advantages, and disadvantages of spectroscopic methods. Includes coverage of the steps used in determining a molecular structure, the limitations to organic structure determination by spectroscopic methods, and an "Organic Structure Analyses Gone Bad" table (all unique to this text)

* Practical Organization: Presents the most commonly used methods first, beginning with an overview of strategies, followed by the use of NMR, and then moving on to mass spectrometry, infrared, and ultraviolet

* Innovative Real-World Problem-Solving Approach: Follows the actual information flow used by chemists to solve molecular structures, as opposed to the standard methods-based approach of other texts

* Unique Chapter (12) Featuring 51 Structure-Solving Problems: Each problem emphasizes a different method; the problems increase in difficulty throughout the chapter, successively building on students' knowledge and requiring them to integrate multiple methods to identify molecules.

NEW TO THE SECOND EDITION

* Coverage of the Latest Instrumental and Computational Advances:
Examines the use of modern instruments, data processing, and computer-assisted structure elucidation techniques

* Updated and Expanded Treatment of NMR (Chapters 2-5): An extensively revised Chapter 5 discusses multi-pulse 1D and 2D NMR methods, 1D TOCSY and 1D NOESY sequences, and using NOESY and ROESY in determining relative stereochemistry and solution conformation.

* Additional Coverage of Mass Spectrometry: A new chapter (7) expands the discussion of mass spectrometry to three chapters (6-8). Topics include cutting-edge MS instrumentation and new information on tandem MS techniques, combining NMR with MS, large-molecule MS, chemo-informatics, and more.

* More Exercises and Improved Spectra: The second edition includes 25% more problems than the previous edition (279 total). In addition, many of the spectra, including all of those presented in Chapters 11 and 12, have been reprocessed or reacquired for greater clarity.

Previous Publication Date(s)

June 1998

Reviews

"Overall this text is more comprehensive and more detailed in introductory descriptions than the classic text in the area, Spectroscopic Methods in Organic Synthesis by Williams and Fleming. It is less of a handbook for PhDs and post-docs and will find its greatest utility as a substantial text for undergraduate teaching. In this respect it is the best around."--David O'Hagen, in Chemistry World

"EL the problems given at the conclusion of each chapter, as well as those comprising the entirety of the final two chapters of the book, should prepare any beginning graduate student in a natural products laboratory for the structure elucidation problems that surely lie ahead."--Joshua N. Fletcher, in Journal of Natural Products

Table of Contents

    Preface
    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 ¹H/¹3C 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 ¹3C 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 ².3 JCH
    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
    Index