Organic Structure Analysis / Edition 2

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Overview

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.

An Instructor's Resource CD-ROM, which includes all of the figures from the text in electronic format and the solutions to all of the exercises and problems from the text (in an editable Word file format), is also available for adopting professors. Please contact your publisher sales representative.

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.

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Editorial Reviews

From the Publisher
"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

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Product Details

  • ISBN-13: 9780195336047
  • Publisher: Oxford University Press
  • Publication date: 10/29/2009
  • Edition description: New Edition
  • Edition number: 2
  • Pages: 656
  • Sales rank: 822,144
  • Product dimensions: 8.96 (w) x 11.50 (h) x 1.14 (d)

Meet the Author

all in the Department of Chemistry at University of California, Santa Cruz
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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

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