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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]
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| Temas: | |
| Acceso en línea: | Texto completo |
MARC
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| 100 | 1 | |a Seco, J. M. |q (José Manuel) |1 https://id.oclc.org/worldcat/entity/E39PCjvmB4yPP3CFRt7tXWCBbm | |
| 245 | 1 | 4 | |a The assignment of the absolute configuration by NMR using chiral derivatizing agents : |b a practical guide / |c José M. Seco, Emilio Quiñoá and Ricardo Riguera. |
| 264 | 1 | |a New York, NY : |b Oxford University Press, |c [2015] | |
| 264 | 4 | |c ©2015 | |
| 300 | |a 1 online resource : |b illustrations | ||
| 336 | |a text |b txt |2 rdacontent | ||
| 337 | |a computer |b c |2 rdamedia | ||
| 338 | |a online resource |b cr |2 rdacarrier | ||
| 504 | |a Includes bibliographical references and index. | ||
| 588 | 0 | |a Print version record. | |
| 505 | 0 | |a 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. | |
| 505 | 8 | |a 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. | |
| 505 | 8 | |a 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. | |
| 505 | 8 | |a 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. | |
| 505 | 8 | |a 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. | |
| 520 | |a 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 covering the practical aspects of the assignment, with examples and spectra taken from the authors' own experiments. Upper-level undergraduates, graduate students, and chemical researchers will find this guide useful for their studies and practice. | ||
| 590 | |a ProQuest Ebook Central |b Ebook Central Academic Complete | ||
| 650 | 0 | |a Nuclear magnetic resonance spectroscopy. | |
| 650 | 0 | |a Spectrum analysis. | |
| 650 | 0 | |a Nuclear magnetic resonance spectroscopy |v Problems, exercises, etc. | |
| 650 | 0 | |a Spectrum analysis |v Problems, exercises, etc. | |
| 650 | 2 | |a Magnetic Resonance Spectroscopy | |
| 650 | 4 | |a Nuclear magnetic resonance spectroscopy |x Problems, exercises, etc. | |
| 650 | 4 | |a Nuclear magnetic resonance spectroscopy. | |
| 650 | 4 | |a Spectrum analysis |x Problems, exercises, etc. | |
| 650 | 4 | |a Spectrum analysis. | |
| 650 | 6 | |a Spectroscopie de la résonance magnétique nucléaire. | |
| 650 | 6 | |a Spectroscopie de la résonance magnétique nucléaire |v Problèmes et exercices. | |
| 650 | 7 | |a SCIENCE |x Chemistry |x Analytic. |2 bisacsh | |
| 650 | 7 | |a Nuclear magnetic resonance spectroscopy |2 fast | |
| 650 | 7 | |a Spectrum analysis |2 fast | |
| 655 | 7 | |a Problems and exercises |2 fast | |
| 700 | 1 | |a Quiñoá, E. |q (Emilio) |1 https://id.oclc.org/worldcat/entity/E39PBJhH4TYWWBBqJ8JMhPfrMP | |
| 700 | 1 | |a Riguera, R. |q (Ricardo) |1 https://id.oclc.org/worldcat/entity/E39PBJkD9MrYMg9tBWMgtP7PwC | |
| 758 | |i has work: |a The assignment of the absolute configuration by NMR using chiral derivatizing agents (Text) |1 https://id.oclc.org/worldcat/entity/E39PCGGJ7G6CQ4cBRmF9RGPWQm |4 https://id.oclc.org/worldcat/ontology/hasWork | ||
| 776 | 0 | 8 | |i Print version: |a Seco, J.M. (José Manuel). |t Assignment of the absolute configuration by NMR using chiral derivatizing agents |z 9780199996803 |w (DLC) 2014042823 |w (OCoLC)894183698 |
| 856 | 4 | 0 | |u https://ebookcentral.uam.elogim.com/lib/uam-ebooks/detail.action?docID=3564608 |z Texto completo |
| 880 | 8 | |6 505-00/(S |a 2.4.6. 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-AMA -- 3.1.4. 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 -- 3.1.9. Example 6: Assignment of the Absolute Configuration of (−)-Borneol Using MTPA -- 3.1.10. Summary -- 3.2. β-Chiral Primary Alcohols -- 3.2.1. Assignment of β-Chiral Primary Alcohols as 9-AMA Esters -- 3.2.2. Example 7: Assignment of the Absolute Configuration of (S)-2-Methylbutan-1-ol Using 9-AMA -- 3.2.3. Absolute Configuration of Primary Alcohols with Polar Groups as 9-AMA Esters -- 3.2.4. Example 8: Assignment of the Absolute Configuration of (S)-2-Chloropropan-1-ol Using 9-AMA -- 3.2.5. Summary -- 3.3. Aldehyde Cyanohydrins -- 3.3.1. Assignment of Aldehyde Cyanohydrins as MPA Esters -- 3.3.2. Example 9: Assignment of the Absolute Configuration of (R)-2-Hydroxy-3-Methylbutanenitrile Using MPA. | |
| 880 | 8 | |6 505-00/(S |a 3.3.3. Example 10: Assignment of the Absolute Configuration of (R)-2-Hydroxy-2-(4-Methoxyphenyl)Acetonitrile Using MPA and 13C NMR -- 3.3.4. Summary -- 3.4. Ketone Cyanohydrins -- 3.4.1. Assignment of Ketone Cyanohydrins as MPA Esters -- 3.4.2. Example 11: Assignment of the Absolute Configuration of (1R, 2S, 5R)-1-Hydroxy-2-Isopropyl-5-Methylcyclohexanecarbonitrile Using MPA -- 3.4.3. Example 12: Assignment of the Absolute Configuration of (S)-2-Hydroxy-2,4-Dimethylpentanenitrile Using MPA and 13C NMR -- 3.4.4. Summary -- 3.5. Secondary Thiols -- 3.5.1. MPA and 2-NTBA Thioesters of Secondary Thiols -- 3.5.2. Example 13: Assignment of the Absolute Configuration of (S)-Butane-2-Thiol Using MPA -- 3.5.3. Example 14: Assignment of the Absolute Configuration of (R)-Ethyl 2-Mercaptopropanoate Using 2-NTBA -- 3.5.4. Example 15: Assignment of the Absolute Configuration of (R)-Ethyl 2-Mercaptopropanoate Using 2-NTBA and 13C NMR -- 3.5.5. Summary -- 3.6. α-Chiral Primary Amines -- 3.6.1. BPG as the CDA for α-Chiral Primary Amines -- 3.6.2. Example 16: Assignment of the Absolute Configuration of (−)-Isopinocampheylamine Using BPG -- 3.6.3. Example 17: Assignment of the Absolute Configuration of (S)-Butan-2-Amine Using BPG and 13C NMR -- 3.6.4. MPA as the CDA for α-Chiral Primary Amines -- 3.6.5. Example 18: Assignment of the Absolute Configuration of (−)-Bornylamine Using MPA -- 3.6.6. MTPA as the CDA for α-Chiral Primary Amines -- 3.6.7. Example 19: Assignment of the Absolute Configuration of (−)-Bornylamine Using MTPA -- 3.6.8. Summary -- 3.7. α-Chiral Carboxylic Acids -- 3.7.1. 9-AHA Esters of Carboxylic Acids -- 3.7.2. Example 20: Assignment of the Absolute Configuration of (S)-3-(Acetylthio)-2-Methylpropanoic Acid Using 9-AHA -- 3.7.3. Summary -- 4 Assignment of the Absolute Configuration of Monofunctional Compounds by Single Derivatization. | |
| 880 | 8 | |6 505-00/(S |a 4.1. Low-Temperature NMR Procedure for Secondary Alcohols -- 4.1.1. Example 21: Assignment of the Absolute Configuration of Diacetone D-Glucose Using (R)-MPA -- 4.1.2. Example 22: Assignment of the Absolute Configuration of (R)-Butan-2-ol Using (S)-MPA -- 4.2. Complexation with Ba2+: MPA Esters of Secondary Alcohols -- 4.2.1. Example 23: Assignment of the Absolute Configuration of (R)-Pentan-2-ol Using (S)-MPA -- 4.2.2. Example 24: Assignment of the Absolute Configuration of (R)-Pentan-2-ol Using (R)-MPA -- 4.3. Complexation with Ba2+: MPA Amides of α-Chiral Primary Amines -- 4.3.1. Example 25: Assignment of the Absolute Configuration of (−)-Isopinocampheylamine Using (R)-MPA -- 4.4. Esterification Shifts -- 4.4.1. Example 26: Assignment of the Absolute Configuration of (1R, 4S)-Hydroxycyclopent-2-en-1-yl Acetate as (R)-9-AMA Ester -- 4.4.2. Example 27: Assignment of the Absolute Configuration of (1R, 4S)-Hydroxycyclopent-2-en-1-yl Acetate as (S)-9-AMA Ester -- 4.5. Summary -- 5 Assignment of the Absolute Configuration of Polyfunctional Compounds -- 5.1. Sec/Sec-1,2- and Sec/Sec-1,n-Diols -- 5.1.1. Double-Derivatization Methods: MPA, 9-AMA, and MTPA -- 5.1.2. Example 28: Assignment of the Absolute Configuration of Heptane-2,3-Diol (Syn) -- 5.1.3. Example 29: Assignment of the Absolute Configuration of Heptane-2,3-Diol (Anti) -- 5.1.4. Example 30: Assignment of the Absolute Configuration of 1,4-Bis-O-(4-Chlorobenzyloxy)-D-Threitol (Syn) Using 13C NMR -- 5.1.5. Single-Derivatization Methods: MPA -- 5.1.6. Example 31: Assignment of the Absolute Configuration of a Pure Isomer of 3,4-Dihydroxy-5-Methylhexan-2-One -- 5.1.7. Example 32: Assignment of the Absolute Configuration of Another Isomer of 3,4-Dihydroxy-5-Methylhexan-2-One -- 5.1.8. Summary -- 5.2. Sec/Sec-1,2-Amino Alcohols -- 5.2.1. Double-Derivatization Method: MPA. | |
| 880 | 8 | |6 505-00/(S |a 5.2.2. Example 33: Assignment of the Absolute Configuration of 2-Aminopentan-3-ol (Syn) -- 5.2.3. Example 34: Assignment of the Absolute Configuration of Methyl 4-Amino-3-Hydroxy-5-Phenylpentanoate (Anti) -- 5.2.4. Summary -- 5.3. Prim/Sec-1,2-Diols -- 5.3.1. Double-Derivatization Methods: MPA -- 5.3.2. Example 35: Assignment of the Absolute Configuration of (S)-Propane-1,2-Diol Using MPA -- 5.3.3. Double-Derivatization Methods: 9-AMA -- 5.3.4. Example 36: Assignment of the Absolute Configuration of (S)-Propane-1,2-Diol Using 9-AMA -- 5.3.5. Example 37: Assignment of the Absolute Configuration of (R)-2,3-Dihydroxypropyl Stearate Based Only on the Methylene Hydrogens -- 5.3.6. Example 38: Assignment of the Absolute Configuration of (R)-1-Phenylethane-1,2-Diol Based Only on the Methylene Hydrogens -- 5.3.7. Single-Derivatization Method: MPA -- 5.3.8. Example 39: Assignment of the Absolute Configuration of (S)-Propane-1,2-Diol -- 5.3.9. Example 40: Assignment of the Absolute Configuration of (R)-Propane-1,2-Diol -- 5.3.10. Summary -- 5.4. Sec/Prim-1,2-Amino Alcohols -- 5.4.1. Double-Derivatization Methods: MPA and the Use of R and Methylene Hydrogens -- 5.4.2. Example 41: Assignment of the Absolute Configuration of (S)-2-Aminopropan-1-ol Based on R and Methylene Hydrogens -- 5.4.3. Double-Derivatization Methods: The Use of OMe and CαH Signals for Assignment -- 5.4.4. Example 42: Assignment of the Absolute Configuration of (S)-2-Aminopropan-1-ol Using ΔδRS of OMe and CαH signals -- 5.4.5. Example 43: Assignment of the Absolute Configuration of (S)-2-Aminopropan-1-ol Using the Separation of OMe and CαH Signals -- 5.4.6. Example 44: Assignment of the Absolute Configuration of (R)-2-Amino-3-Methylbutan-1-ol Using the Separation of OMe and CαH Signals -- 5.4.7. Single-Derivatization Method: MPA. | |
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