Discrimination of chiral compounds using NMR spectroscopy:
Gespeichert in:
| Beteilige Person: | |
|---|---|
| Format: | Buch |
| Sprache: | Englisch |
| Veröffentlicht: |
Hoboken, N.J.
Wiley
2007
|
| Schlagwörter: | |
| Links: | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025426292&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| Beschreibung: | Table of contents only: http://www.loc.gov/catdir/toc/ecip072/2006033572.html |
| Umfang: | xxiii, 549 s. ill |
Internformat
MARC
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| 020 | |z 9780471763529 (alk. paper) |9 978-0-471-76352-9 (alk. paper) | ||
| 035 | |a (OCoLC)600966850 | ||
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| 084 | |a VE 5700 |0 (DE-625)147119:253 |2 rvk | ||
| 084 | |a VG 9500 |0 (DE-625)147241:253 |2 rvk | ||
| 100 | 1 | |a Wenzel, Thomas J. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Discrimination of chiral compounds using NMR spectroscopy |c Thomas J. Wenzel |
| 264 | 1 | |a Hoboken, N.J. |b Wiley |c 2007 | |
| 300 | |a xxiii, 549 s. |b ill | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Table of contents only: http://www.loc.gov/catdir/toc/ecip072/2006033572.html | ||
| 650 | 4 | |a Chemical tests and reagents | |
| 650 | 4 | |a Nuclear magnetic resonance spectroscopy | |
| 650 | 4 | |a Enantiomers / Derivatives | |
| 650 | 4 | |a Chirality | |
| 650 | 4 | |a Derivatization | |
| 650 | 4 | |a NMR-spektroskopi | |
| 650 | 0 | 7 | |a NMR-Spektroskopie |0 (DE-588)4075421-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Chirale Verbindungen |0 (DE-588)4348527-3 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Chirale Verbindungen |0 (DE-588)4348527-3 |D s |
| 689 | 0 | 1 | |a NMR-Spektroskopie |0 (DE-588)4075421-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 856 | 4 | 2 | |m HBZ Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025426292&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-025426292 | |
Datensatz im Suchindex
| _version_ | 1819314625955495936 |
|---|---|
| adam_text | CONTENTS
Preface xxi
Acknowledgments xxiii
1. Introduction 1
1.1. Chiral Derivatizing Agents 1
1.2. Chiral Solvating Agents 2
1.3. Overview of Chiral Reagents and Methodologies 4
1.4. Future Prospects 6
2. Aryl-Containing Carboxylic Acids 8
2.1. Introduction 8
2.2. a-Methoxy-a-trifluoromethylphenylacetic Acid
(MTPA-Mosher s Reagent) 11
2.2.1. Analysis of Secondary Alcohols 13
2.2.2. Analysis of Secondary Diols and Polyols 19
2.2.3. Analysis of Primary Alcohols 25
2.2.4. Analysis of Tertiary Alcohols 26
2.2.5. Analysis of Secondary Amines 26
2.2.6. Analysis of Primary Amines 28
2.2.7. Use as a Chiral Solvating Agent 29
2.2.8. Use of MTPA Derivatives with Paramagnetic
Lanthanide Chelates 30
2.2.9. Use of MTPA Derivatives with Diamagnetic
Lanthanide Chelates 34
vii
viü CONTENTS
2.2.10. Preparation of MTPA Derivatives 35
2.2.11. Liquid Chromatography-NMR Spectroscopy
of MTPA Derivatives 35
2.2.12. Database Methods with MTPA 35
2.3. a-Methoxyphenylacetic Acid (Omethyl Mandelic Acid-MPA) 38
2.3.1. Analysis of Secondary Alcohols 39
2.3.2. Analysis of Diols 42
2.3.3. Analysis of Primary Alcohols 43
2.3.4. Analysis ofAmines 44
2.3.5. Analysis of Sulfoxides 45
2.3.6. Variable-temperature Method for Assigning
Absolute Stereochemistry 46
2.2.7. Barium(II) Method for Assigning
Absolute Stereochemistry 47
2.3.8. Use of MPA Derivatives with Lanthanide Chelates 48
2.3.9. Use as a Chiral Solvating Agent 49
2.3.10. Preparation of MPA Derivatives-The
Mix and Shake Method 50
2.4. Mandelic Acid (2-Hydroxy-2-phenyl Acetic Acid) (MA) 51
2.5. O-Acetyl Mandelic Acid (2-Acetoxy-2-phenyl
Acetic Acid) (0-AMA) 53
2.6. Tetrahydropyranyl-protected Mandelic Acid [(2R)-2-phenyl-2-
[(2S)-tetrahydro-2-pyranyloxy] Ethanoic Acid] 56
2.7. O-Nitromandelic Acid 56
2.8. 2-Phenylpropionic Acid (2-PPA) 57
2.9. 2-Methoxy-2-phenylpropionic Acid 58
2.10. 3-Phenylbutanoic Acid (3-PBA)/2-Phenylbutanoic
Acid (2-PBA) 58
2.11. a-Methyl-a-methoxy(pentafluorophenyl) (Acetic Acid) 60
2.12. a-Cyano-a-fiuorophenylacetic Acid
(CFPA)/oc-Cyano-a-fluoronaphthylacetic Acid
(CFNA)/a-Cyano-oc-fluoro-/?-tolylacetic Acid (CFTA) 60
2.13. jV-Boc Phenylglycine (BPG) 62
2.14. 1,5-Difluoro-2,4-dinitrobenzene and Derivatives 63
2.14.1. JV-(5-Fluoro-2,4-dinitrophenyl)-1 -phenylethylamide 64
2.14.2. l-Fluoro-2,4-dinitrophenyl~5-(5 alanine Amide
(Marfey s Reagent) 65
2.15. 2-Fluoro-2-phenylacetic Acid/2-Fluoro-2-(l-naphthyl)propionic
Acid/2-Fluoro-2-(2-naphthyl)propionic Acid 66
2.16. a-Methoxy-a-(l-naphthyl) Acetic Acid
(1 -NM A)/a-Methoxy- x-(2-naphthy 1) Acetic Acid (2-NMA) 67
2.17. 2-(l-Naphthyl)-2-phenylacetic Acid 70
2.18. 2-Methoxy-2-( 1 -naphthyl) Propionic Acid (MaNP) 71
2.19. l-Methoxy-2,3-dihydro-l#-cyclopenta[a]naphthalene-
1-carboxylic Acid 72
CONTENTS ix
2.20. O-Aryl Lactic Acids 72
2.21. a-(2-Anthryl)~cc-methoxyacetic Acid
(2-AMA)/a-(9-Anthryl)-a-methoxyacetic Acid (9-AMA) 74
2.22. (a-[l-(9-Anthryl)]-2,2,2-trifluoroethoxy)acetic Acid 78
2.23. 2-Methoxy-2-(9-phenanthryl)propionic Acid 78
2.24. Summary 79
2.24.1. Analysis of Primary Alcohols 79
2.24.2. Analysis of Secondary Alcohols 79
2.24.3. Analysis of Tertiary Alcohols 80
2.24.4. Analysis of Primary Amines 80
2.24.5. Analysis of Secondary Amines 81
3. Other Carboxylic Acid-based Reagents 82
3.1. Camphanic Acid 82
3.2. Menthoxyacetic Acid (MAA) 86
3.3. 2-(2,3-Anthracenedicarboximido)cyclohexane
Carboxylic Acid 87
3.4. 3ß-Acetoxy-A5-etiocholenic Acid 88
3.5. Naproxen 89
3.6. 2-ter?-Butyl-2-methyl-l,3-benzodioxole-4-carboxylic Acid 90
3.7. en io-3-Benzamidonorbornane-2-carboxylic Acid 90
3.8. Coumarin-based Reagents 91
3.9. 2,2-Diphenylcyclopropane Carboxylic Acid 91
3.10. Amide Derivatives of Kemp s Triacid 91
3.11. AminoAcids 92
3.11.1. N-Boc-phenylalanine 92
3.11.2. Isotopically Substituted Amino Acids 92
3.12. (/?)-(-)-(2,3,5,7-Tetranitro-9-fluorenyloximino)propanoic Acid 93
3.13. 2-Chloropropanoic Acid (2-C1-PA) 93
3.14. Chlorofluoroacetic Acid 94
3.15. Perfiuoropropoxy Propionic Acid/Perfluoro
Isopropropoxy Propionic Acid 94
3.16. 2-Methylbutyric Acid 94
3.17. Lactic Acid and Derivatives 95
3.17.1. Trifluorolactic Acid 95
3.17.2. (S O-Acetyllactylchloride 95
3.18. Lasalocid 96
3.19. Axial Chiral Carboxylic Acids 96
3.19.1. (+)-1 -[2-Carboxy-6-(trifluoromethyl)phenyl]pyrrole-
2-carboxylic Acid 96
3.19.2. 2 -Methoxy-l,l -binaphthyl-2-carboxylic Acid (MBNC) 97
3.19.3. 2 -Methoxy-l,l -binaphthalene-8-carboxylic Acid 98
3.19.4. 2 -Octylcarbamoyl-l,l -binaphthyl-2-dicarboxylic Acid 100
3.19.5. 2-(2 -Methoxy-r-naphthyl)-3,5-dichlorobenzoic
Acid (MNCB) 100
x CONTENTS
4. Hydroxyl- and Thiol-Containing Reagents 102
4.1. 2,2,2-Trifluorophenylethanol(TFPE) 103
4.2. 2,2,2-Tnflüoro-l-(9-anthryl)ethanol
(Pirkle s Alcohol (TFAE) 109
4.2.1. AnalysisofS ulfoxides 109
4.2.2. Analysis of Lactones 110
4.2.3. Analysis of Lactams 111
4.2.4. Analysis of Oxaziridines 112
4.2.5. Analysis of Axial Chiral Compounds 112
4.2.6. Analysis of Compounds that are Chiral by
Virtue of SIow Rotation 113
4.2.7. Analysis ofMetal Complexes 115
4.2.8. Analysis of Cyclophosphazenes 116
4.2.9. Analysis of Phosphine Oxides 117
4.2.10. Analysis of Calixarenes 118
4.2.11. Analysis of Other Substrates 119
4.2.12. Use of Lanthanide Chelates with TFPE and TFAE 122
4.2.13. Use as a Chiral Derivatizing Agent 123
4.3. Other Anthryl-based Reagents 123
4.3.1. Analogs of TFAE 123
4.3.2. Ethyl-2-(9-anthryI)-2-hydroxyacetate 126
4.3.3. 2-(2,3~Anthracenedicarboximido)~l-cyclohexanol 127
4.4. 2,2,2-Trifluoro-l-(l~pyrenyl)ethanol 127
4.5. 2-(Trifluoromethyl)benzhydrol 127
4.6. 1-Phenylethanol 128
4.7. Methyl Mandelate (MM) 129
4.8. Octahydro-8,9,9-trimethyl-5,8-methano-2#-l-
benzopuran-2-ol (Noe s Reagent) 130
4.9. Menthol 132
4.10. Bomeol 135
4.11. (-)-lO-Mercaptoisoborneol 135
4.12. (^H-)-Pantolactone 136
4.13. /ra«j-Bis(hydroxydiphenylrnethyl)-
2,2-dimethyl-1,3-dioxacyclopentane 136
4.14. 2-Hydroxymethyl-4,6-dimethyl-2-phenyl-l,3-dioxane 137
4.15. 2-Butanol 137
4.16. Assignment of Absolute Configuration
Using Glycosidation Shifts 138
4.16.1. Analysis of Di- and Polysaccharides 141
4.16.2. ß-D-and ß-L-Fucofuranoside/Arabinofuranoside 142
4.17. Linear Dextrins 144
4.18. Axial Chiral (Atropoisomeric) Alcohols 144
4.18.1. 2,2 -Dihydroxy-1,1 -binaphthalene (BINOL) 145
4.18.2. 8,8 -Dihydroxy-1,1 -binaphthalene 147
CONTENTS Xi
4.18.3. Alkyl-Substituted Binaphthols 147
4.18.4. 2 -Hydroxy-l,l -binaphthyl-2-yl[(3,5-dinitrobenzoyl)
amino](phenyl)acetate 148
4.18.5. 1,6-Di(o-chlorophenyl)-1,6-diphenylhexa-
2,4-diyne-l,6-diol 148
4.18.6. 4,4 6,6 -Tetrachloro-2,2 -bis(hydroxydiphenylmethyl)
biphenyl 148
4.19. Diol and Dithiol Reagents 149
4.19.1. Butane-2,3-diol/Butane-2,3-thioI 149
4.19.2. 2,2-Dimethyl-l,3-propanediol 150
4.19.3. l,l,2-Triphenyl-l,2-ethanediol 151
4.19.4. Ethylene Dithiol 151
4.19.5. a,a,a ,a -Tetraphenyl-l,3-dioxolane-4,5-dimethanols)
(TADDOL) 151
5. Amine-based Reagents 153
5.1. Primary Amines 154
5.1.1. 1-Phenylethylamine (PEA)/1-(1-Naphthyl)ethylamine
(NEA)/l-(9-Anthryl)ethylamine (AEA) 154
5.1.2. Fluorinated Aryl Amines 161
5.1.3. 9-( 1 - Amino-2,2-dimethylpropyl)-9,10-
dihydroanthracene 161
5.1.4. (lS,25)-l-Phenyl-2-amino-3-methoxy-l-propanol 162
5.1.5. Phenylglycinol 163
5.1.6. l-(3-Aminopropyl)-(5/?,85,10Ä)terguride 163
5.1.7. 5-Amino-4-aryl-2,2-dimethyl-l,3-dioxans 164
5.1.8. Amino Acids 164
5.1.8.1. Peptides 164
5.1.8.2. Phenylglycine methyl ester (PGME)/
Phenylglycine dimethyl-amide 165
5.1.8.3. L-Cysteine 168
5.1.8.4. L-Proline 169
5.1.9. (lÄ,2Ä)-l-(l ,8 -Naphthalimide)-2-aminocyclohexane
Derivatives 169
5.1.10. l-(l-Naphthyl)-2,2-dimethylpropylamine 170
5.1.11. 1 -Methoxy-2-aminopropane 170
5.1.12. (+)-2-Amino-l-methoxymenth-8-ene 171
5.2. Secondary Amines 171
5.2.1. Ephedrine 171
5.2.2. 2-Methyl Piperidine 173
5.2.3. (Af-Methyl)-a-isosparteiniumcation 174
5.2.4. N-Boc-l-(l-naphthyl)ethylamine 174
5.2.5. yV-Methyl-D-(-)-ghicamine 175
5.2.6. (5)-2-(Diphenylmethyl)pyrrolidine 175
xjj CONTENTS
5.3. Tertiary Amines 175
5.3.1. Quinine/Cinchonidine/Quinidine 175
5.3.2. 2,8-Dimethyl-6^,12H-5,ll-methanodibenzo[b,f][l,5]
diazocine (Troger s Base) 180
5.3.3. Brucine 180
5.3.4. Strychnine 181
5.3.5. (R)- and (5)-Tetrahydroisoquinoline 181
5.4. Diamine Reagents 182
5.4.1. l,2-Diphenyl-l,2-diaminoethane 182
5.4.2. A^V -Substituted l,2-diphenyl-l,2-diaminoethane 183
5.5. Databases Using Amine Chiral Solvating Agents 184
5.5.1. Ma-Dimethylbenzylamine (DMBA) 184
5.5.2. Bis-l,3-methylbenzylamine-2-methylpropane(BMBA-pMe) 187
5.5.3. (7?-cx-Methoxy-a-trifluoromethylphenylacetic Acid
(MTPA)/BMBA-pMe 189
6. Miscellaneous Organic-based Chiral Derivatizing
and Solvating Agents 190
6.1. Amides 191
6.1.1. Af-(3,5-Dinitrobenzoyl)-l-phenylethylamine(DNB-PEA) 191
6.1.2. A -(3,5-Dinitrobenzoyl)-L-leucine(DNB-Leu) 193
6.1.3. AL(3,5-Dinitrobenzoyl)phenylglycine 195
6.1.4. A^(3,5-Dinitrobenzoyl)-4-amino-3-methyl-1,2,3,4-
tetrahydrophenanthrene (Whelk-O-1) 195
6.1.5. AM-(1-Naphthyl)ethyltrifluoroacetamide 196
6.1.6. 1-(1-Naphthyl)ethyl Urea Derivatives
of Amino Acids (NEU-AA) 197
6.1.7. Bis Allyl Amide Derivatives 198
6.1.7.1. /VyV -Diallyl-L-tartardiamide
fcw(4-terf-butylbenzoate) 198
6.1.7.2. (S,S)-trans-Acenaphthene-1,2-dicarboxylic
acid bis allylamide 198
6.1.8. (Ä)-Phenylglycinol-A -3,5-dinitrobenzoyl-C -
triethoxysilylpropylcarbamate 198
6.1.9. /V-Methy] Amide of (R)-N-Acetyl-4-methoxy Phenyl
Glycine 199
6.1.10. /V-(n-Butylamide) of (S)-2-Phenylcarbamoyloxypropionic
Acid 199
6.1.11. 2,2 -Oxybis[A^-( 1 -phenylethyl)acetamidej 200
6.1.12. Tetrapeptide Species 200
6.1.13. Tetraamidic Selector 200
6.2. Lactams 201
6.2.1. Dihydropyrimidone 202
6.2.2. Amino Acid Isocyanurate Derivatives 202
CONTENTS xiii
6.3. Aldehydes 203
6.3.1. 15-Formyl-14-hydroxy-2,8-dithia[9](2,5)
pyridinophane 203
6.3.2. 2 -Methoxy-l,l -binaphthalene-8-carbaldehyde 203
6.3.3. 2-Hydroxy-2 -nitrobenzoate-3-aldehyde-l,l -
binaphthalene 204
6.3.4. 2-Hydroxy-2 -substituted-3-aldehyde-l,l -
binaphthalene 205
6.4. Ketones 205
6.4.1. 1-Menthone 205
6.4.2. (S)-(+)-2-Propylcyclohexanone 206
6.5. Isocyanates 206
6.5.1. 1-Phenylethyl Isocyanate (PE-I) 206
6.5.2. 1-(1-Naphthyl)ethyl Isocyanate (NE-I) 208
6.5.3. Phenylethy Isothiocyanate (PE-IS)/Naphthylethyl
Isothiocyanate (NE-IS) 209
6.5.4. a-Methoxy-a-(trifluoromethyl)benzyl Isocyanate 210
6.5.5. 2,3,4,6-Tetra-O-acetyl-ß-D-glucopyranosyl
Isothiocyanate 210
6.5.6. (S)-2-Chloro-2-fluoroethanoyl Isocyanate 211
6.6. Miscellaneous Reagents 211
6.6.1. 2,2-Dimethoxypropane 211
6.6.2. (-)-Chloromethylmenthyl Ether 212
6.6.3. 2-Oxazolidones 213
6.6.4. 5(fi)-Methyl-l-(chloromethyl)-2-pyrrolidinone 214
6.6.5. 5-Methyl-5-phenylpyrroline N-oxide 215
6.6.6. (S 2[(/?)-Fluoro(phenyl)methyl]oxirane 215
6.6.7. (S)-Triazine Selector 216
6.6.8. 2-Deuterio-2,3-dihydro-2-methyl-6-
nitrobenzothiophene-1 -oxide 216
6.6.9. 3a-Benzhydryl-3,3a,4,5-tetrahydro-2//-
cyclopenta[b]furan 217
6.6.10. Camphor-10-sulfonic Acid(CSA) 217
6.6.11. Menthyl Chloroformate 219
6.6.12. (N-Methylphenylsulfoximidoyl)methyl Lithium 220
6.6.13. Coumarin Dimer 221
6.6.14. Di-O-benzoyl Tartrate/Di-O-p-toluoyl Tartrate 221
6.6.15. Dibenzoyl-L-tartaric Acid Anhydride 222
6.6.16. DNA 223
6.6.17. 5,8-Bis(aminomethyl)-1,12-dimethylbenzo[c]
phenanthrene 223
6.6.18. 2 -Methoxy-1,1 -binaphthalene-2-
carbohydroxymoyl Chloride (MBCC) 223
6.7. Self-discrimination of Chiral Compounds 224
6.8. High-throughput Optical Purity Measurements 227
xjv CONTENTS
7. Reagents Incorporating Phosphorus, Selenium, Boron,
and Silicon Atoms 229
7.1. Phosphorus-containing Reagents 230
7.1.1. Phosphorus(V) Reagents 230
7.1.1.1. Phosphimc Amides (Phos 1) 230
7.1.1.2. Phosphinothioic Acids (Phos2) 231
7.1.1.3. cw-2-Chloro-3,4-dimethyl-5-phenyl-1,3,2-
oxazophospholidin-2-one (Phos3) 234
7.1.1.4. (2-Chloro-4(/?),5(/?)-dimethyl-2-oxo-1,3,2-
dioxaphospholane (Phos4) 236
7.1.1.5. L-Menthylphenylchlorophosphine Oxide (Phos5) 236
7.1.1.6. 2-Chloro-5,5~dimethyl-4-phenyl-1,3,2-
dioxaphosphorinane-2-oxide (Phosö) 236
7.1.1.7. O,O-Di-(2-(5)-(A^^V-diethyl-2-hydroxypropyl)
phosphonate (Phos7) 237
7.1.1.8. 2-Chloro~3-phenyl-1,3,2-diazaphosphabicyclo
[3.3.0Joctane-2-oxide (Phos8) 238
7.1.1.9. Methyl Phosphonic Dichloride (Phos9)/
Methyl Phosphonothioic Dichloride (Phos 10) 239
7.1.1.10. (9,0-Diphenyldithioic Acid(Phosll) 239
7.1.1.11. l,l -Binaphthyl-2,2 -diylphosphoricAcid(Phosl2) 240
7.1.2. Phosphorus(III) Reagents 242
7.1.2.1. Diazaphospholidines(Phosl3-Phos20) 242
7.1.2.2. l,3,2-Dioxaphospholanes(Phos21-Phos27) 246
7.1.2.3. Dimenthyl Chlorophosphite (Phos28) 248
7.1.2.4. Dichloromenthylphosphine (Phos29) 248
7.1.2.5. Phosphorus Trichloride (Phos30) 249
7.1.2.6. Hexaalkylphosphorus Triamides (Phos31) 249
7.1.2.7. a-1-Phenylethylamino Trisaminoamine (Phos32) 249
7.1.2.8. [5] HELOL Phosphite (Phos33) 249
7.1.3. lonic Reagents—TRISPHAT, BINPHAT, and BINTROP 250
7.1.4. Configurational Analysis of Phosphates 260
7.1.4.1. Oxygen Isotope Methods 260
7.1.4.2. ROESYStudies 263
7.1.5. Summary 264
7.2. Selenium-containing Reagents 264
7.2.1. 4-MethyI-5-phenyIoxazolidine-2-selone 264
7.2.2. (/?,Ä)-AW-DimethyIcycIohexyl-1,2-diazaselenophospholine 266
7.2.3. 2-Phenylselenopropionic Acid 267
7.2.4. 1,2,3-Selenadiazoles 267
7.3. Boron-containing Reagents 268
7.3.1. 2-(l-Methoxyethyl)phenylboronic Acid 268
7.3.2. Phenylboronic Acid 269
7.3.3. Boric Acid [B(OH)3] 270
CONTENTS XV
7.3.4. Camphanylboronic Acid 270
7.3.5. 4S,5Ä-4-Methyl-5-phenyl-l,3,2-oxazaborolidine
(Ephedrine Borane) 271
7.3.6. (S)-(+)-N-Acetylphenylglycine Boronic Acid 271
7.3.7. l-Benzamido-l-(2-methylphenyl)methaneboronic Acid 271
7.3.8. 2-Formylphenylboronic Acid 272
7.3.9. 2,2/-(l,2-Phenylene)bis[(4Ä,5/?)-4,5-diphenyl-
1,3,2-dioxaboroIane 272
7.3.10. (l-Chloroalkyl)boronates 273
7.4. Silyl-containing Reagents 274
7.4.1. Menthylphenylsilylacetic Acid 274
7.4.2. (Benzylmethylphenylsilyl)methylamine 274
7.4.3. Monochlorosilanes 275
8. Host Compounds as Chiral NMR Discriminating Agents 278
8.1. Cyclodextrins 279
8.1.1. Introduction 279
8.1.2. Native Cyclodextrins 280
8.1.2.1. Lanthanide Coupling to Native Cyclodextrins 286
8.1.3. Neutral Cyclodextrin Derivatives 287
8.1.3.1. Hexakis(2,3,6-tri-0-methyl)-oc-cyclodextrin
(TM-a-CD)/Heptakis(2,3,6-tri-0-methyl)-
ß-cyclodextrin (TM-ß-CD) - (Permethyl CDs) 287
8.1.3.2. Heptakis(2,6-di-O-methyl)-ß-cyclodextrin
(2,6-DM-ß-CD) 289
8.1.3.3. Benzylated and Benzoylated Cyclodextrins 290
8.1.3.4. Carbamoylated Cyclodextrins 290
8.1.3.5. Octakis(3-O-butanoyl-2,6-di-O-pentyl)-
y-cyclodextrin (BP-CD) 291
8.1.3.6. Hydroxyethyl and Hydroxypropyl
Cyclodextrins (HE-CD, HP-CD) 291
8.1.3.7. Heptakis(2,3-di~O-acetyl)-ß-CD(2,3-DA-ß-CD) 291
8.1.3.8. Mono(2-acetylamino-2-deoxy)-, Mono
(3-acetylamino-3-deoxy)- and Mono
(6-acetylamino-6-deoxy)-ß-cyclodextrin
(AA-ß-CD) 292
8.1.3.9. Mono-3,6-anhydro-ß-cyclodextrin 292
8.1.3.10. Heptakis(3-O-acetyl-2,6-di-0-pentyl)-
ß-cyclodextrin 292
8.1.3.11. Octakis(2,6-di-O-pentyl-3-0-
trifluoroacetyl)-y-cyclodextrin 292
8.1.3.12. Cyanoethylated-ß-cyclodextrin 292
8.1.3.13. Per-0-octyl-oc-cyclodextrin 293
8.1.3.14. Biphenyl-capped-ß-cyclodextrin 293
8.1.3.15. Heptakis(2,3,6-tri-O-acetyl)-ß-CD(TA-ß-CD) 293
xvj CONTENTS
8.1.4. Anionic Cyclodextnn Derivatives 293
8.1.4.1. Carboxymethylated Cyclodextrins (CM-CD) 293
8.1.4.2. Heptakis(6-carboxymethylthio-6-deoxy)-
ß-cyclodextrin (6-CMT-ß-CD) 296
8.1.4.3. Sulfobutylether-ß-cyclodextrin(SBE-ß-CD) 296
8.1.4.4. Heptakis(2,3-di-(9-acetyl-6-sulfo)-ß-CD
(HDAS-ß-CD) 297
8.1.4.5. Sulfated Cyclodextrins (S-CD) 298
8.1.5. Cationic Cyclodextnn Derivatives 298
8.1.5.1. Amino-substituted Cyclodextrins 298
8.1.5.2. Bis(6-trimethylammonio)-ß-cyclodextrin
(TMA-ß-CD) 299
8.1.5.3. Mono(6-xylylenediamine)-ß-cyclodextrin(X-ß-CD) 299
8.1.6. Summary 299
8.2. Crown Ethers 300
8.2.1. Introduction 300
8.2.2. (18-Crown-6)-2,3,ll,12-tetracarboxylic Acid
(18-C-6-TCA) 301
8.2.2.1. Amide Derivatives of (18-Crown-6)-2,3,11,12-
tetracarboxylic Acid 303
8.2.3. (18-Crown-6)-2,3,ll,12-derivatives 303
8.2.4. Crown Ethers Incorporating a 2,2 -Dihydroxy-l,l -
binaphthalene Unit 305
8.2.5. Glycoside-derived Crown Ethers 305
8.2.6. Crown Ether-like Compounds with
Nitrogen-heterocyclic Units 306
8.2.7. Triazole-18-crown-6Ether 308
8.2.8. Crown Ether-like Compounds with Phenol Units 308
8.2.9. Aza Crown Ethers 309
8.3. Calixarenes and Calixresorcarenes 311
8.3.1. Introduction 311
8.3.2. Calix[4]resorcarenes 312
8.3.3. Calixarenes 315
8.3.4. Summary 319
8.4. Receptor Compounds for Carboxylic Acids 320
8.5. Cyclic Peptides 323
8.6. Miscellaneous Receptor Compounds 324
8.6.1. Cyclic Tetraamidic Reagent 324
8.6.2. Cyclosophoraoses (Cyclic(l-2)-ß-D-glucans) 325
8.6.3. Glycophane Receptor 325
8.6.4. Cyclophane Receptors 326
8.6.5. Cryptophane Receptor 326
8.6.6. Receptor for Secondary Amines 327
8.6.7. Spirobisindane Receptor 327
8.6.8. Receptors for Diols 328
8.6.9. l,l -Binaphthalene-based Receptors 328
CONTENTS xvii
8.7. Enzymes 329
8.7.1. Calmodulin 329
8.7.2. Chymotrypsin 330
9. Chiral Discrimination with Metal-based Reagents 331
9.1. Introduction 331
9.2. Lanthanide Complexes 332
9.2.1. Introduction 332
9.2.2. Peak Broadening with Lanthanide Shift Reagents 335
9.2.3. Catalytic Properties of Lanthanide Ions 337
9.2.4. Application of Lanthanide tris ß-diketonates 338
9.2.1.1. Discrimination of Prochiral Nuclei 339
9.2.1.2. Analysis of Deuterium-Substituted
Compounds 341
9.2.1.3. Analysis of Compounds Chiral by Virtue
of Slow Rotation 342
9.2.4.1. Analysis of Compounds Chiral by Virtue
of Geometrical Constraints 344
9.2.5. Miscellaneous Applications of Lanthanide
tris ß-diketonates 346
9.2.6. Analysis of Chiral Metal Complexes 348
9.2.7. Assignment of Absolute Stereochemistry 351
9.2.8. Pr(III) Complex of Tetraphenylimidodiphosphinate—
Pr(tpip)3 354
9.2.9. Binuclear Lanthanide-silver Reagents 355
9.2.9.1. Analysis of Organic Salts 358
9.2.10. Aqueous Lanthanide Shift Reagents 359
9.2.10.1. Complexes of Propylenediaminetetraacetate
(pdta) 360
9.2.10.2. Complexes of AWV,./V-Tetrakis(pyridylmethyl)
propylene Diamine (TPPN) 361
9.2.10.3. Complexes with Other Ligands 362
9.2.10.4. Complexes with Tetraazocyclodecane
Macrocyclic Ligands 364
9.3. Transition Metal Complexes 365
9.3.1. Palladium Complexes 365
9.3.1.1. Bridged Dimers with Amine Ligands 365
9.3.1.2. Miscellaneous Palladium Complexes 372
9.3.2. Platinum Complexes 374
9.3.2.1. Complexes with Diphosphine Ligands 374
9.3.2.2. Complexes with Amine Ligands 375
9.3.2.3. Analysis of Geometrical Isomers 378
9.3.3. Rhodium Complexes 378
9.3.3.1. Rhodium Dimer—[Rh2(MTPA)4] 378
9.3.3.2. Miscellaneous Rhodium Complexes 384
xviü CONTENTS
9.3.4. Cobalt Complexes 385
9.3.4.1. Complexes with Porphyrin Ligands 385
9.3.4.2. Analysis of Geometrical Isomers 387
9.3.4.3. Analysis of DNA 389
9.3.5. Zinc Complexes 389
9.3.6. Ruthenium Complexes 392
9.3.7. Nickel Complexes 394
9.3.8. Copper Complexes 394
9.3.9. Silver Complexes 395
9.3.10. Tin Complexes 396
9.3.11. Titanium Complexes 397
9.3.12. Tungsten Complexes 397
9.3.13. Molybdenum Complexes 397
9.3.14. Mercury Complexes 397
9.3.15. Osmium Complexes 398
9.3.16. Uranium Complexes 398
10. Chiral NMR Discrimination with Highly
Ordered Systems 399
10.1. Introduction 399
10.2. Liquid Crystals 400
10.2.1. Introduction 400
10.2.2. Early Studies with Liquid Crystals 401
10.2.3. 2H NMR Analysis of Labeled Compounds 403
10.2.4. Natural Abundance 2H NMR Analysis 410
10.2.5. 13C NMR Analysis 412
10.2.6. HNMR Analysis 414
10.2.7. 19F NMR Analysis 414
10.2.8. Analysis Using Other Nuclei 415
10.2.9. Miscellaneous Studies with Liquid
Crystals 415
10.3. Micelles and Gels 416
10.4. lonic Liquids 419
10.5. Polymers 420
10.5.1. Cellulose-carbamate Polymers 420
10.5.2. Poly 3- and 4-((S-(oc-Methylbenzylcarbamoyl)
phenyl Isocyanate 421
10.5.3. Poly(ester/ß-sulfoxides) 421
10.5.4. Chirasil-val 422
10.5.5. Poly(AM-anthrylmaleimide) 422
10.5.6. Poly [(l-6)-2,5-anhydro-3,4-di-O-methyl-
D-glucitol] 423
CONTENTS xix
10.6. Aggregation of Achiral Compounds into Chiral Assemblies 423
10.7. Solid-state NMR Spectroscopy 425
10.7.1. Tri-0-thymotide Clathrates 425
10.7.2. Cholic Acid Channels 426
10.7.3. Analysis of Polymer-bound Compounds 427
References 428
Index 537
|
| any_adam_object | 1 |
| author | Wenzel, Thomas J. |
| author_facet | Wenzel, Thomas J. |
| author_role | aut |
| author_sort | Wenzel, Thomas J. |
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| dewey-ones | 543 - Analytical chemistry |
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| dewey-search | 543/.66 |
| dewey-sort | 3543 266 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| id | DE-604.BV040598500 |
| illustrated | Illustrated |
| indexdate | 2024-12-20T16:18:17Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-025426292 |
| oclc_num | 600966850 |
| open_access_boolean | |
| owner | DE-384 |
| owner_facet | DE-384 |
| physical | xxiii, 549 s. ill |
| publishDate | 2007 |
| publishDateSearch | 2007 |
| publishDateSort | 2007 |
| publisher | Wiley |
| record_format | marc |
| spellingShingle | Wenzel, Thomas J. Discrimination of chiral compounds using NMR spectroscopy Chemical tests and reagents Nuclear magnetic resonance spectroscopy Enantiomers / Derivatives Chirality Derivatization NMR-spektroskopi NMR-Spektroskopie (DE-588)4075421-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| subject_GND | (DE-588)4075421-2 (DE-588)4348527-3 |
| title | Discrimination of chiral compounds using NMR spectroscopy |
| title_auth | Discrimination of chiral compounds using NMR spectroscopy |
| title_exact_search | Discrimination of chiral compounds using NMR spectroscopy |
| title_full | Discrimination of chiral compounds using NMR spectroscopy Thomas J. Wenzel |
| title_fullStr | Discrimination of chiral compounds using NMR spectroscopy Thomas J. Wenzel |
| title_full_unstemmed | Discrimination of chiral compounds using NMR spectroscopy Thomas J. Wenzel |
| title_short | Discrimination of chiral compounds using NMR spectroscopy |
| title_sort | discrimination of chiral compounds using nmr spectroscopy |
| topic | Chemical tests and reagents Nuclear magnetic resonance spectroscopy Enantiomers / Derivatives Chirality Derivatization NMR-spektroskopi NMR-Spektroskopie (DE-588)4075421-2 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| topic_facet | Chemical tests and reagents Nuclear magnetic resonance spectroscopy Enantiomers / Derivatives Chirality Derivatization NMR-spektroskopi NMR-Spektroskopie Chirale Verbindungen |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025426292&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT wenzelthomasj discriminationofchiralcompoundsusingnmrspectroscopy |