Organic Structure Analysis / Edition 2

by Phillip Crews, Jaime Rodriguez, Marcel Jaspars

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.

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.

Product Details

ISBN-13:	9780195336047
Publisher:	Oxford University Press
Publication date:	10/29/2009
Series:	Topics in Organic Chemistry
Edition description:	New Edition
Pages:	656
Product dimensions:	8.96(w) x 11.50(h) x 1.14(d)

About the Author

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

Table of Contents

, PrefaceCHAPTER 1.USING SPECTROSCOPIC DATA IN ORGANIC STRUCTURE ANALYSIS1.1 A Glimpse of the Methods in Common Use1.2 Characteristics of the Methods in Common Use1.3 Steps in Establishing a Molecular Structure1.4 Molecular Formula (MF) and Unsaturation Number (UN)1.5 Substructures, Working Structures, and Final Structures1.6 Limitations of Spectroscopic Data in Structure AnalysisCHAPTER 2. INTRODUCTION TO NUCLEAR MAGNETIC RESONANCE2.1 A Glimpse of the NMR Phenomenon2.2 Commonly Studied Nuclei2.3 Obtaining an NMR Spectrum2.4 Magnetic Shielding2.5 Relaxation Effects2.6 Effect of Relaxation and NOE on Peak Intensities2.7 Electric Quadrupole Effects2.8 Measurement and Presentation of Data2.9 Sample Preparation and Sample Size2.10 Common Impurities in NMR Spectra2.11 Other Useful NucleiCHAPTER 3. INTERPRETATION AND USE OF PROTON AND CARBON CHEMICAL SHIFTS3.1 A Glimpse of Chemical Shifts and Peak Areas3.2 Terms and Conventions3.3 Factors That Determine Chemical Shifts3.4 Chemical Shift Positions of ¹H/¹3C Attached to Common Functional Groups3.5 Chemical Shift Equivalence3.6 Characteristic Chemical Shifts for Different Protons and Carbons3.7 Using Databases to Estimate ¹3C NMR Chemical Shifts3.8 Making Configurational Assignments Based on Chemical Shifts: Case ExamplesCHAPTER 4. INTERPRETATION AND USE OF PROTON AND CARBON COUPLING CONSTANTS4.1 A Glimpse of Coupling Constants4.2 First-Order Spectra and the n + 1 Rule4.3 Terms and Conventions4.4 Common Coupled Spin Systems4.5 Magnetic Nonequivalence4.6 Using Coupling Constants to Understand the Appearance of Spectra and Make Assignments4.7 Coupling Constant Values for Different Carbon and Proton Types4.8 Using Coupling Constants to Make Configurational Assignments4.9 Ways to Simplify or Eliminate Coupling Effects4.10 The Nuclear Overhauser effect4.11 Additional Ways to Obtain J ValuesCHAPTER 5. MULTIPLE-PULSE AND MULTIDIMENSIONAL NMR TECHNIQUES5.1 A Glimpse of Multiple-Pulse NMR Methods5.2 Elements of Multiple-Pulse NMR5.3 One-Dimensional NMR Techniques5.4 Two-Dimensional NMR Techniques5.5 Using Two-Dimensional NMR in Assigning Spectra5.6 Using Two-Dimensional NMR Data to Determine an Unknown Structure5.7 Strategies for Using 2D NMR in Structure Determination5.8 Use of NOESY and ROESY to Determine Relative Stereochemistry and Conformations5.9 Specialized Pulse Sequences5.10 Configurational Analysis Based on Coupling Constants: Experimental Measurement of ².3 JCH5.11 Computer-Assisted Structure Elucidation5.12 Future Prospects in Multidimensional NMRCHAPTER 6. MASS SPECTROMETRY: CORE TECHNIQUES AND IONIZATION PROCESSES6.1 A Glimpse of Mass Spectrometry6.2 Measurement, Presentation of Data, and Nomenclature6.3 Isotopes, Atomic Composition, Molecular Formulas, and Ionic Mass: Low and High Resolution and Measurements6.4 Different Ionization Techniques in Mass Spectrometry6.5 Different Techniques for Analyzing Ions in Mass Spectrometry6.6 Detectors in Mass Spectrometry6.7 Hyphenated Mass Spectrometry6.8 Tandem Mass Spectrometry6.9 Future ProspectsCHAPTER 7. MASS SPECTROMETRY ANALYSIS OF SMALL AND LARGE MOLECULES7.1 A Glimpse of Molecular Ions Revisited7.2 Small-Molecule Mass Spectral Analysis7.3 Large-Molecule Mass Spectrometry7.4 Future ProspectsCHAPTER 8. FRAGMENTATION PROCESSES IN ELECTRON IONIZATION MASS SPECTROMETRY8.1 A Glimpse of Fragmentation in Mass Spectrometry8.2 Interpreting a Low Resolution Electron Ionization Mass Spectrum8.3 Fragmentation Processes8.4 Identification of Functionality from Fragmentation Processes8.5 Schematic Approach for the Interpretation of an EIMSCHAPTER 9. INFRARED SPECTROSCOPY9.1 A Glimpse of Infrared Spectroscopy9.2 Measurement and Presentation of Data9.3 The Fundamentals9.4 Identifying Functional Groups9.5 Interpreted Infrared Spectra9.6 Use of Infrared DatabasesCHAPTER 10. OPTICAL AND CHIROPTICAL TECHNIQUES: ULTRAVIOLET SPECTROSCOPY10.1 A Glimpse of Ultraviolet Spectroscopy10.2 Measurement and Presentation of Data10.3 The Fundamentals for Interpreting Spectra10.4 Identifying Functional Groups10.5 Theoretical Simulations of UV Spectra10.6 The Behavior of Chiral Chromophores ORD/CD10.7 The Exciton Chirality Method10.8 Other Ways to Examine Chiral ChromophoresCHAPTER 11. STRATEGIES OF DETERMINING STRUCTURE AND STEREOCHEMISTRY: SPECTROSCOPIC DATA TRANSLATED INTO STRUCTURES11.1 A Glimpse of the Combined Use of Spectroscopic Data11.2 The Strategies of Determining Structure and Stereochemistry11.3 Dereplication Strategies11.4 Worked Examples of Deriving Structures from Spectroscopic DataCHAPTER 12. PROBLEMS IN ORGANIC STRUCTURE ANALYSIS12.1 A Glimpse of the Scope of the 51 Unknowns12.2 Using the Spectra, Accompanying Information, and Other ResourcesAPPENDICESA. Collections of Spectra or Data TablesB. Shape of MS ClustersC. CAS Registry Numbers for UnknownsD. Glossary and Abbreviations, Index

Editorial 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

"… 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

From the Publisher