Cargando…
The assignment of the absolute configuration by NMR using chiral derivatizing agents : a practical guide /
The Assignment of the Absolute Configuration by NMR Using Chiral Derivatizing Agents: A Practical Guide briefly explains the theoretical aspects necessary for understanding the methodology of new research in the field of Nuclear magnetic resonance spectroscopy (NMR), dedicating most of its space to...
| Clasificación: | Libro Electrónico |
|---|---|
| Autor principal: | |
| Otros Autores: | , |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
New York, NY :
Oxford University Press,
[2015]
|
| Temas: | |
| Acceso en línea: | Texto completo |
Tabla de Contenidos:
- Cover; The Assignment of the Absolute Configuration by NMR Using Chiral Derivatizing Agents; Copyright; Contents; Preface; Introduction; 1 The Theoretical Basis for Assignment by NMR; 1.1. Distinguishing Enantiomers by NMR: The Use of CDAs; 1.2. Structural Characteristics of the Auxiliaries and the Substrates; 1.3. Importance of the Conformation; 1.4. Importance of the Aromatic Shielding Effect; 1.5. Use of 13C NMR for Assignment; 1.6. Simplified Approaches to Assignment by NMR; 1.6.1. Single-Derivatization Method: Manipulating the Conformational Equilibrium by Temperature.
- 1.6.2. Single-Derivatization Method: Manipulating the Conformational Equilibrium by Complexation1.6.3. Single-Derivatization Method Based on Esterification Shifts; 1.6.4. Mix-and-Shake Method: Assignment Using Resin-Bound CDAs; 1.7. General Criteria for the Correct Application of the NMR Methodology; 1.8. Correlation Models for the Assignment of Polyfunctional Compounds; 1.9. Summary; 2 Practical Aspects of the Preparation of the Derivatives; 2.1. Instrumentation, Concentration, Solvent, and Temperature of the NMR Experiment; 2.2. Source and Preparation of the CDAs.
- 2.3. Preparation of the CDA Esters, Thioesters, and Amides2.3.1. Derivatization of Alcohols, Thiols, and Cyanohydrins Using the CDA Acid; 2.3.2. Derivatization of Amines Using the CDA Acid; 2.3.3. Preparation of the CDA Acid Chlorides; 2.3.4. Derivatization of Alcohols, Thiols, and Cyanohydrins Using the CDA Acid Chloride; 2.4. Resin-Bound CDA Derivatives (Mix-and-Shake Method); 2.4.1. Preparation of Resin-Bound CDA Derivatives; 2.4.2. Preparation of Acid Chloride Resins; 2.4.3. Preparation of CDA-Resins; 2.4.4. Determination of the Loading of the CDA-Resins.
- 2.4.5. In-Tube Derivatization of Amines2.4.6. In-Tube Derivatization of Primary and Secondary Alcohols, Cyanohydrins, and Secondary Thiols; 2.4.7. In-Tube Derivatization of Amino Alcohols; 2.4.8. In-Tube Derivatization of Diols and Triols; 2.4.9. In-Tube Derivatization for Single-Derivatization Procedures; 3 Assignment of the Absolute Configuration of Monofunctional Compounds by Double Derivatization; 3.1. Secondary Alcohols; 3.1.1. MPA and 9-AMA as CDAs for Secondary Alcohols; 3.1.2. Example 1: Assignment of the Absolute Configuration of Diacetone D-Glucose Using MPA.
- 3.1.3. Example 2: Assignment of the Absolute Configuration of (
- )-Isopulegol Using 9-AMA3.1.4. Example 3: Assignment of the Absolute Configuration of (R)-Butan-2-ol Using MPA and 13C-NMR; 3.1.5. Simultaneous Derivatization of the Substrate with the (R)- and (S)-CDAs; 3.1.6. Example 4: Assignment of the Absolute Configuration of (S)-Butan-2-ol Using a 1:2 Mixture of (R)- and (S)-MPA; 3.1.7. Example 5: Assignment of the Absolute Configuration of (
- )-Menthol Using a 2:1 Mixture of (R)- and (S)-9-AMA and 13C NMR; 3.1.8. MTPA as the CDA for Secondary Alcohols.