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Mass Spectrometry of Non-Covalent Complexes: Supramolecular Chemistry in the Gas Phase

ISBN: 978-0-470-13115-2
571 pages
September 2009
Mass Spectrometry of Non-Covalent Complexes: Supramolecular Chemistry in the Gas Phase (0470131152) cover image
Details the many benefits of applying mass spectrometry to supramolecular chemistry

Except as a method for the most basic measurements, mass spectrometry (MS) has long been considered incompatible with supramolecular chemistry. Yet, with today's methods, the disconnect between these two fields is not warranted. Mass Spectrometry and Gas-Phase Chemistry of Non-Covalent Complexes provides a convincing look at how modern MS techniques offer supramolecular chemists a powerful investigatory toolset.

Bringing the two fields together in an interdisciplinary manner, this reference details the many different topics associated with the study of non-covalent complexes in the gas phase. The text begins with brief introductions to supramolecular chemistry and such relevant mass spectrometric methods as ionization techniques, analyzers, and tandem MS experiments. The coverage continues with:

  • How the analyte's transition into the gas phase changes covalent bonding

  • How limitations and pitfalls in analytical methods may produce data misinterpretations

  • Artificial supramolecular aggregates and their examination

  • Biomolecules, their complexes, and their examination

After the general remarks making up the first section of the book, the following sections describe specific experimental procedures and are illustrated with numerous examples and short tutorials. Detailed citations end each chapter. Mass spectrometrists, supramolecular chemists, students in these fields, and interested readers from other disciplines involving the study of non-covalent bonds will all value Mass Spectrometry and Gas-Phase Chemistry of Non-Covalent Complexes as an innovative and practical resource.

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Preface.

List of Tutorials.

PART A: GENERAL ISSUES.

1. INTRODUCTION.

2. SUPRAMOLECULAR CHEMISTRY: SOME BACKGROUND.

2.1. The Nature of Non-Covalent Interactions.

2.2. Classical Building Blocks in Supramolecular Chemistry.

2.3. Key Areas and Key Concepts in Supramolecular Chemistry.

2.4. Biomolecules: Intra- and Intermolecular Non-Covalent Bonds.

References.

3 MASS SPECTROMETRY FOR THE EXAMINATION OF NON-COVALENT COMPLEXES.

3.1. Common Mass Spectrometric Instrumentation for the Examination of Non-Covalent Bonds.

3.2. How Non-Covalent Bonds Change on the Transition from Solution to the Gas Phase.

3.3. Ion Energetics Issues.

3.4. Tandem-MS-Experiments.

3.5. Potential Sources of Error or Misinterpretation.

References.

PART B: ARTIFICIAL SUPRAMOLECULAR SYSTEMS. 

4 FUNDAMENTAL STUDIES ON SMALLER NON-COVALENT COMPLEXES.

4.1. Ion Neutral Complexes.

4.2. High-Pressure Mass Spectrometry: Bridging the Gap Between Gas and Condensed Phase.

References.

5 DETERMINATION OF THE "SECONDARY STRUCTURE" OF SUPRAMOLECULES BY MASS SPECTROMETRY.

5.1. Mechanically Interlocked Molecules and Their Precursors.

5.2. Guest Encapsulation.

5.3. Gas-Phase Conformations.

5.4. Zwitterions and Salt-Bridges.

References.

6 CHIRAL RECOGNITION.

6.1. Tartrate Clusters.

6.2. Chiral Crown Ether-Ammonium Complexes: The Three-Point Model.

6.3. Cyclodextrin-Amino Acid Recognition.

6.4. Chiral Recognition in Amino Acid Clusters.

6.5. Homochiral Serine Octamers.

6.6. Resonant Two Photon Ionization Studies of Chiral Complexes: Spectroscopy of Diastereomeric Complexes in the Gas Phase.

References.

7 MONITORING SOLUTION REACTIVITY OF NON-COVALENT COMPLEXES BY MASS SPECTROMETRY.

7.1. Mass Spectrometric Characterization of Metallo-Supramolecular Aggregates.

7.2. Simple Ligand Exchanges in Metallo-Supramolecular Squares.

7.3. Titration Experiments with Helicates.

7.4. Helicates Again: Mechanistic Insight into Ligand Exchange Reactions.

7.5. Titration Experiments with Self-Sorting Tetraurea-Calixarenes.

7.6. Self-Sorting Reactions of Pseudorotaxane Assemblies.

7.7. Shorter Time-Scales: A Mixed-Flow Technique Applied to Self-Assembly.

References.

8. GAS-PHASE REACTIVITY OF SUPRAMOLECULES.

8.1. Molecular "Mouse Traps": Covalent Bond Formation Within Non-Covalent Complexes.

8.2. Fragmentation of Metallo-Supramolecular Helicates, Squares, and Cages.

8.3. Host-Guest Chemistry of Dendrimers in the Gas Phase.

8.4. H/D Exchange Reactions in Gaseous Non-Covalent Complexes.

References.

9 DETERMINATION OF THERMOCHEMICAL DATA.

9.1. Crown Ether Binding Affinities in Solution.

9.2. Ranking of Anion-Cavitand Gas-Phase Binding Energies.

9.3. Crown Ether-Ammonium Ion Complexes in the Gas Phase.

9.4. Crown Ether-Alkali Metal Ion Complexes and the Best-Fit Model.

References.

PART C NON-COVALENT COMPLEXES OF BIOMOLECULES.

10 NON-COVALENT COMPLEXES WITH PETIDES AND PROTEINS.

10.1. Metal-Ion Binding to Peptides and Small Proteins.

10.2. Probing Three-Dimensional Protein Structure and Protein-Protein Interactions.

10.3. Interactions of Proteins with Small Molecules.

10.4. Sugar-Peptide and Sugar-Protein Complexes.

10.5. Interactions of Proteins with Oligonucleotides, DNA, and RNA.

References.

11. NON-COVALENT COMPLEXES OF NUCLEOTIDES.

11.1. Metal-Ion Binding to DNA Bases and Oligonucleotides.

11.2. Are Watson-Crick Base Pairing and Double Helix Conserved in the Gas Phase?

11.3. G-Quartets.

11.4. The Folding of G-Rich Strands into Quadruplexes.

11.5. Minor Groove Binders and Intercalators: The Binding to Duplexes.

11.6. Non-Covalent Interactions With G-Quadruplexes.

References.

12. CARBOHYDRATES.

12.1 Carbohydrates: Their Importance and Analysis.

12.2. Stereodifferentiation of Small Carbohydrates.

12.3. Structural Aspects of Oligosaccharides by MS and IMS.

12.4. Carbohydrate Association.

12.5. Summary and Outlook.

References.

13. EPILOGUE.

Index.

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Christoph A. Schalley, PhD, is a professor of organic chemistry at Freie Universität Berlin. He received his PhD with Helmut Schwarz at the Technische Universität Berlin followed by a postdoctorate with Julius Rebek, Jr., at The Scripps Research Institute in California. He has authored more than 120 publications and edited seven books. He was awarded the Dozentenstipendium in 2004 of the Fonds der Chemischen Industrie and the Mattauch-Herzog Prize from the German Society of Mass Spectrometry in 2006.

Andreas Springer, PhD, received his PhD from the Humboldt-Universität zu Berlin for work with Prof. Michael Linscheid. Currently, he is head of the mass spectrometry core facility of the Department of Chemistry at Freie Universität Berlin, where he is running — besides a collection of up-to-date instruments — one of the oldest, still working EI sector-field instruments worldwide.

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"Whether the reader is a mass spectrometrist or a supramolecular chemist ... both are accommodated." (Book News, December 2009)
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