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An expert resource for chemists using stereochemical analysis methods
In Chiral Separations and Stereochemical Elucidation: Fundamentals, Methods, and Applications, a team of distinguished researchers delivers a robust and authoritative discussion of the theoretical fundamentals of chiral separation, the most commonly used chiral selectors, and stereochemical elucidation methods. The book offers expert discussions of a variety of chiral separation methods by gas chromatography (GC), supercritical fluid chromatography (SFC), capillary electrophoresis (CE), and liquid chromatography (LC).
The authors also describe several methods for stereochemical elucidation, including X-ray crystallography, nuclear magnetic resonance spectroscopy, and chiroptical methods. The explored material is ideal for practicing chemists seeking a resource to help them guide method development and optimization or to explain quality control-complements during target compound production.
Readers will also find:
* A thorough introduction to the most important advances and applications in LC, GC, CE, SFC, and preparative chromatography
* Comprehensive explorations of the role of 2D-LC for chiral separation methods development and applications
* Practical discussions of the design, mechanisms, and applications of the most commonly used chiral selectors
* Fulsome treatments of the theoretical backgrounds, advantages, limitations, and applications of stereochemical elucidation methods
Perfect for academic and industrial chemists specially in organic, analytical chemistry and pharmaceutical analysis. Chiral Separations and Stereochemical Elucidation: Fundamentals, Methods, and Applications will also benefit biochemists, environmental analysts, forensic and medicinal chemists as well as natural product chemists and those involved with stereochemistry or structural elucidation.
List of contents
List of Contributors xv
Preface xix
Part I Fundamentals of Chiral Separation 1
1 Chiral Separation by LC 3
Juliana Cristina Barreiro and Quezia Bezerra Cass
1.1 Introduction 3
1.2 Workflow for LC Chiral Method Development 7
1.3 New Column Technologies 9
1.4 Selected Examples of Fast Separation 12
1.5 Chiral 2D- LC 14
1.5.1 LC-LC and mLC-LC 14
1.5.2 LC × LC and sLC × LC 17
1.6 Future and Perspectives 19
References 20
2 Chiral Separation by GC 27
Oliver Trapp
2.1 Introduction 27
2.2 Chiral Recognition in Gas Chromatography 29
2.2.1 Chiral Recognition by Hydrogen Bonding 31
2.2.2 Chiral Recognition Using Chiral Metal Complexes 31
2.2.3 Chiral Recognition by Host-Guest Interactions 31
2.3 Preparation of Fused- Silica Capillaries for GC with CSPs 33
2.4 Application of CSPs in Chiral Gas Chromatography 34
2.4.1 CSPs with Diamide Selectors 34
2.4.1.1 Chirasil- Val 34
2.4.2 CSPs with CD Selectors 35
2.4.2.1 Heptakis(2,3,6- tri- O- Methyl)- ß- Cyclodextrin (Permethyl- ß- Cyclodextrin) 38
2.4.2.2 Heptakis(2,3,6- tri- O- Methyl)- ß- Cyclodextrin Immobilized to Hydrido Dimethyl Polysiloxane (Chirasil- ß- Dex) 39
2.4.2.3 Heptakis(2,6- di- O- Methyl- 3- O- Pentyl)- ß- Cyclodextrin 43
2.4.2.4 Hexakis- (2,3,6-tri- O- Pentyl)- alpha- Cyclodextrin 47
2.4.2.5 Heptakis(2,3,6- tri- O- Pentyl)- ß- Cyclodextrin 48
2.4.2.6 Hexakis- (3- O- Acetyl- 2,6- di- O- Pentyl)- alpha- Cyclodextrin 51
2.4.2.7 Heptakis(3- O- Acetyl- 2,6- di- O- Pentyl)- ß- Cyclodextrin 51
2.4.2.8 Octakis(3- O- Butyryl- 2,6- di- O- Pentyl)- gamma- Cyclodextrin 53
2.4.2.9 Hexakis/Heptakis/Octakis(2,6- di- O- Alkyl- 3- O- Trifluoroacetyl)- alpha/ß/gamma- Cyclodextrins 57
2.4.2.10 Heptakis(2,3- di- O- Acetyl- 6- O-tert- Butyldimethylsilyl)- ß- Cyclodextrin (DIAC- 6- TBDMS- ß- CD) 58
2.4.2.11 Heptakis(2,3- di- O- Methyl- 6- O-tert- Butyldimethylsilyl)- ß- Cyclodextrin (DIME- 6- TBDMS- ß- CD) 58
2.4.3 Cyclofructans 62
2.4.4 CSPs with Metal Complexes 65
2.5 Conclusion 69
References 69
3 Chiral Separation by Supercritical Fluid Chromatography 85
Emmanuelle Lipka
3.1 Introduction 85
3.2 Characteristics and Properties of Supercritical Fluids 87
3.3 Development of a Chiral SFC Method 89
3.3.1 Chiral Stationary Phases 89
3.3.2 Mobile Phases 91
3.3.2.1 Mobile Phase: Type of Co- solvent Used 93
3.3.2.2 Mobile Phase: Percentage of Co- solvent Used 94
3.3.2.3 Mobile Phase: Use of Additives 94
3.4 Operating Parameters 94
3.4.1 Effect of the Flow Rate 95
3.4.2 Effect of the Outlet Pressure (Back- pressure) 95
3.4.2.1 Effect of Pressure When the Mobile Phase is a Gas- Like Fluid 96
3.4.2.2 Effect of Pressure When the Mobile Phase is a Liquid- Like Fluid 97
3.4.3 Effect of Temperature 97
3.4.3.1 Effect of Temperature When the Mobile Phase is a Gas- Like Fluid 98
3.4.3.2 Effect of Temperature When the Mobile Phase is a Liquid- Like Fluid 98
3.5 Detection 99
3.6 Scale- Up to Preparative Separation 99
3.7 Conclusion 100
References 101
4 Chiral Separation by Capillary Electrophoresis and Capillary Electrophoresis-Mass Spectrometry: Fundamentals, Recent Developments, and Applications 103
Charles Clark, Govert W. Somsen, and Isabelle Kohler
4.1 Introduction 103
4.2 Principles of Chiral CE 105
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About the author
Quezia Bezerra Cass, PhD, is a Full Professor of Chemistry at Universidade Federal de São Carlos, São Carlos, SP, Brazil.
Maria Elizabeth Tiritan, PhD, is an Assistant Professor of Organic Chemistry at Universidade do Porto, Porto, Portugal.
João Marcos Batista Junior, PhD, is an Assistant Professor of Chemistry at Universidade Federal de São Paulo, São José dos Campos, SP, Brazil.
Juliana Cristina Barreiro, PhD, is a Researcher in Chemistry at Universidade de São Paulo, São Carlos, SP, Brazil.
