Organic Structure Analysis

by Crews, Phillip; Rodriguez, Jaime; Jaspars, Marcel

• ISBN13: 9780195336047
• ISBN10: 0195336046
• Edition: 2nd
• Format: Hardcover
• Copyright: 2009-10-29
• Publisher: Oxford University Press

Summary

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. Organic Structure Analysis, Second Edition, is supplemented by 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). 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.

Table of Contents

Preface

Using Spectroscopic Data In Organic Structure Analysis

A Glimpse of the Methods in Common Use

Characteristics of the Methods in Common Use

Steps in Establishing a Molecular Structure

Molecular Formula (MF) and Unsaturation Number (UN)

Substructures, Working Structures, and Final Structures

Limitations of Spectroscopic Data in Structure Analysis

Introduction To Nuclear Magnetic Resonance

A Glimpse of the NMR Phenomenon

Commonly Studied Nuclei

Obtaining an NMR Spectrum

Magnetic Shielding

Relaxation Effects

Effect of Relaxation and NOE on Peak Intensities

Electric Quadrupole Effects

Measurement and Presentation of Data

Sample Preparation and Sample Size

Common Impurities in NMR Spectra

Other Useful Nuclei

Interpretation And Use Of Proton And Carbon Chemical Shifts

A Glimpse of Chemical Shifts and Peak Areas

Terms and Conventions

Factors That Determine Chemical Shifts

Chemical Shift Positions of 1H/13C Attached to Common Functional Groups

Chemical Shift Equivalence

Characteristic Chemical Shifts for Different Protons and Carbons

Using Databases to Estimate 13C NMR Chemical Shifts

Making Configurational Assignments Based on Chemical Shifts: Case Examples

Interpretation And Use Of Proton And Carbon Coupling Constants

A Glimpse of Coupling Constants

First-Order Spectra and the n + 1 Rule

Terms and Conventions

Common Coupled Spin Systems

Magnetic Nonequivalence

Using Coupling Constants to Understand the Appearance of Spectra and Make Assignments

Coupling Constant Values for Different Carbon and Proton Types

Using Coupling Constants to Make Configurational Assignments

Ways to Simplify or Eliminate Coupling Effects

The Nuclear Overhauser effect

Additional Ways to Obtain J Values

Multiple-Pulse And Multidimensional Nmr Techniques

A Glimpse of Multiple-Pulse NMR Methods

Elements of Multiple-Pulse NMR

One-Dimensional NMR Techniques

Two-Dimensional NMR Techniques

Using Two-Dimensional NMR in Assigning Spectra

Using Two-Dimensional NMR Data to Determine an Unknown Structure

Strategies for Using 2D NMR in Structure Determination

Use of NOESY and ROESY to Determine Relative Stereochemistry and Conformations

Specialized Pulse Sequences

Configurational Analysis Based on Coupling Constants: Experimental Measurement of 2.3 JCH

Computer-Assisted Structure Elucidation

Future Prospects in Multidimensional NMR

Mass Spectrometry: Core Techniques And Ionization Processes

A Glimpse of Mass Spectrometry

Measurement, Presentation of Data, and Nomenclature

Isotopes, Atomic Composition, Molecular Formulas, and Ionic Mass: Low and High Resolution and Measurements

Different Ionization Techniques in Mass Spectrometry

Different Techniques for Analyzing Ions in Mass Spectrometry

Detectors in Mass Spectrometry

Hyphenated Mass Spectrometry

Tandem Mass Spectrometry

Future Prospects

Mass Spectrometry Analysis Of Small And Large Molecules

A Glimpse of Molecular Ions Revisited

Small-Molecule Mass Spectral Analysis

Large-Molecule Mass Spectrometry

Future Prospects

Fragmentation Processes In Electron Ionization Mass Spectrometry

A Glimpse of Fragmentation in Mass Spectrometry

Interpreting a Low Resolution Electron Ionization Mass Spectrum

Fragmentation Processes

Identification of Functionality from Fragmentation Processes

Schematic Approach for the Interpretation of an EIMS

Infrared Spectroscopy

A Glimpse of Infrared Spectroscopy

Measurement and Presentation of Data

The Fundamentals

Identifying Functional Groups

Interpreted Infrared Spectra

Use of Infrared Databases

Optical And Chiroptical Techniques: Ultraviolet Spectroscopy

A Glimpse of Ultraviolet Spectroscopy

Measurement and Presentation of Data

The Fundamentals for Interpreting Spectra

Identifying Functional Groups

Theoretical Simulations of UV Spectra

The Behavior of Chiral Chromophores ORD/CD

The Exciton Chirality Method

Other Ways to Examine Chiral Chromophores

Strategies Of Determining Structure And Stereochemistry: Spectroscopic Data Translated Into Structures

A Glimpse of the Combined Use of Spectroscopic Data

The Strategies of Determining Structure and Stereochemistry

Dereplication Strategies

Worked Examples of Deriving Structures from Spectroscopic Data

Problems In Organic Structure Analysis

A Glimpse of the Scope of the 51 Unknowns

Using the Spectra, Accompanying Information, and Other Resources

Appendices

Collections of Spectra or Data Tables

Shape of MS Clusters

CAS Registry Numbers for Unknowns

Glossary and Abbreviations

Index

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