Discrimination of Chiral Compounds Using NMR Spectroscopy

by Wenzel, Thomas J.

ISBN13: 9780471763529

ISBN10: 0471763527

Format: Hardcover

Pub. Date: 2007-04-13

Publisher(s): Wiley-Interscience

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Summary

A comprehensive overview of the use of NMR spectroscopy for chiral discrimination Discrimination of Chiral Compounds Using NMR Spectroscopy concisely covers the broad array of reagents that make it possible to determine the optical purity and assign the absolute configuration of many classes of compounds. It describes chiral NMR derivatizing agents, solvating agents, metal-based reagents, and liquid crystals and discusses the range and types of compounds for which they can be used for analysis. After an overview of chiral reagents and methodologies, this reference: * Includes comprehensive coverage of the chiral reagents that have been reported * Catalogs the range of compounds for which different reagents have been shown to be effective * Includes specialty categories such as liquid crystals, ionic liquids, and the formation of chiral aggregates from achiral building blocks that do not fit into the broader categories * Offers experimental strategies for using the reagents that are likely to improve the quality of the results This guide describes the various systems and their overall utility, but goes further to show the full scope of the field as a way of guiding investigations into the optimal chiral reagents for use in NMR spectroscopy. It's a practical reference for organic chemists in the pharmaceutical industry, academia, and other areas, NMR spectroscopists, and researchers involved in the isolation and structure determination of natural products.

Author Biography

Thomas J. Wenzel, PHD, is the Charles A. Dana Professor of Chemistry at Bates College in Lewiston, Maine. He has received research and educational grants from the National Science Foundation, Research Corporation, the Petroleum Research Fund, the Camille and Henry Dreyfus Foundation, and the Pittsburgh Conference and Exhibition. His most recent research focuses on the development of chiral NMR shift reagents.

Preface	p. xxi
Acknowledgments	p. xxiii
Introduction	p. 1
Chiral Derivatizing Agents	p. 1
Chiral Solvating Agents	p. 2
Overview of Chiral Reagents and Methodologies	p. 4
Future Prospects	p. 6
Aryl-Containing Carboxylic Adds	p. 8
Introduction	p. 8
[alpha]-Methoxy-[alpha]-trifluoromethylphenylacetic Acid (MTPA-Mosher's Reagent)	p. 11
Analysis of Secondary Alcohols	p. 13
Analysis of Secondary Diols and Polyols	p. 19
Analysis of Primary Alcohols	p. 25
Analysis of Tertiary Alcohols	p. 26
Analysis of Secondary Amines	p. 26
Analysis of Primary Amines	p. 28
Use as a Chiral Solvating Agent	p. 29
Use of MTPA Derivatives with Paramagnetic Lanthanide Chelates	p. 30
Use of MTPA Derivatives with Diamagnetic Lanthanide Chelates	p. 34
Preparation of MTPA Derivatives	p. 35
Liquid Chromatography-NMR Spectroscopy of MTPA Derivatives	p. 35
Database Methods with MTPA	p. 35
[alpha]-Methoxyphenylacetic Acid (O-methyl Mandelic Acid-MPA)	p. 38
Analysis of Secondary Alcohols	p. 39
Analysis of Diols	p. 42
Analysis of Primary Alcohols	p. 43
Analysis of Amines	p. 44
Analysis of Sulfoxides	p. 45
Variable-temperature Method for Assigning Absolute Stereochemistry	p. 46
Barium(II) Method for Assigning Absolute Stereochemistry	p. 47
Use of MPA Derivatives with Lanthanide Chelates	p. 48
Use as a Chiral Solvating Agent	p. 49
Preparation of MPA Derivatives-The "Mix and Shake" Method	p. 50
Mandelic Acid (2-Hydroxy-2-phenyl Acetic Acid) (MA)	p. 51
O-Acetyl Mandelic Acid (2-Acetoxy-2-phenyl Acetic Acid) (O-AMA)	p. 53
Tetrahydropyranyl-protected Mandelic Acid [(2R)-2-phenyl-2[(2S)-tetrahydro-2-pyranyloxyl Ethanoic Acid]	p. 56
O-Nitromandelic Acid	p. 56
2-Phenylpropionic Acid (2-PPA)	p. 57
2-Methoxy-2-phenylpropionic Acid	p. 58
3-Phenylbutanoic Acid (3-PBA)/2-Phenylbutanoic Acid (2-PBA)	p. 58
[alpha]-Methyl-[alpha]-methoxy(pentafluorophenyl) (Acetic Acid)	p. 60
[alpha]-Cyano-[alpha]-fluorophenylacetic Acid (CFPA)/[alpha]-Cyano-[alpha]-fluoronaphthylacetic Acid (CFNA)/[alpha]-Cyano-[alpha]-fluoro-p-tolylacetic Acid (CFTA)	p. 60
N-Boc Phenylglycine (BPG)	p. 62
1,5-Difluoro-2,4-dinitrobenzene and Derivatives	p. 63
N-(5-Fluoro-2,4-dinitrophenyl)-1-phenylethylamide	p. 64
1-Fluoro-2,4-dinitrophenyl-5-(S)-alanine Amide (Marfey's Reagent)	p. 65
2-Fluoro-2-phenylacetic Acid/2-Fluoro-2-(1-naphthyl)propionic Acid/2-Fluoro-2-(2-naphthyl)propionic Acid	p. 66
[alpha]-Methoxy-[alpha]-(1-naphthyl) Acetic Acid (1-NMA)/[alpha]-Methoxy-[alpha]-(2-naphthyl) Acetic Acid (2-NMA)	p. 67
2-(1-Naphthyl)-2-phenylacetic Acid	p. 70
2-Methoxy-2-(1-naphthyl) Propionic Acid (M[alpha]NP)	p. 71
1-Methoxy-2,3-dihydro-1H-cyclopenta[a]naphthalene-1-carboxylic Acid	p. 72
O-Aryl Lactic Acids	p. 72
[alpha]-(2-Anthryl)-[alpha]-methoxyacetic Acid (2-AMA)/[alpha]-(9-Anthryl)-[alpha]-methoxyacetic Acid (9-AMA)	p. 74
([alpha]-[1-(9-Anthryl)]-2,2,2-trifluoroethoxy)acetic Acid	p. 78
2-Methoxy-2-(9-phenanthryl)propionic Acid	p. 78
Summary	p. 79
Analysis of Primary Alcohols	p. 79
Analysis of Secondary Alcohols	p. 79
Analysis of Tertiary Alcohols	p. 80
Analysis of Primary Amines	p. 80
Analysis of Secondary Amines	p. 81
Other Carboxylic Acid-based Reagents	p. 82
Camphanic Acid	p. 82
Menthoxyacetic Acid (MAA)	p. 86
2-(2,3-Anthracenedicarboximido)cyclohexane Carboxylic Acid	p. 87
3[beta]-Acetoxy-[Delta]5-etiocholenic Acid	p. 88
Naproxen	p. 89
2-tert-Butyl-2-methyl-1,3-benzodioxole-4-carboxylic Acid	p. 90
Endo-3-Benzamidonorbornane-2-carboxylic Acid	p. 90
Coumarin-based Reagents	p. 91
2,2-Diphenylcyclopropane Carboxylic Acid	p. 91
Amide Derivatives of Kemp's Triacid	p. 91
Amino Acids	p. 92
N-Boc-phenylalanine	p. 92
Isotopically Substituted Amino Acids	p. 92
(R)-(-)-(2,3,5,7-Tetranitro-9-fluorenyloximino)propanoic Acid	p. 93
2-Chloropropanoic Acid (2-C1-PA)	p. 93
Chlorofluoroacetic Acid	p. 94
Perfluoropropoxy Propionic Acid/Perfluoro Isopropropoxy Propionic Acid	p. 94
2-Methylbutyric Acid	p. 94
Lactic Acid and Derivatives	p. 95
Trifluorolactic Acid	p. 95
(S)-O-Acetyllactylchloride	p. 95
Lasalocid	p. 96
Axial Chiral Carboxylic Acids	p. 96
(+)-1-[2-Carboxy-6-(trifluoromethyl)phenyl]pyrrole-2-carboxylic Acid	p. 96
2[prime]-Methoxy-1,1[prime]-binaphthyl-2-carboxylic Acid (MBNC)	p. 97
2[prime]-Methoxy-1,1[prime]-binaphthalene-8-carboxylic Acid	p. 98
2[prime]-Octylcarbamoyl-1,1[prime]-binaphthyl-2-dicarboxylic Acid	p. 100
2-(2[prime]-Methoxy-1[prime]-naphthyl)-3,5-dichlorobenzoic Acid (MNCB)	p. 100
Hydroxyl-and Thiol-Containing Reagents	p. 102
2,2,2-Trifluorophenylethanol (TFPE)	p. 103
2,2,2-Trifluoro-1-(9-anthryl)ethanol (Pirkle's Alcohol (TFAE)	p. 109
Analysis of Sulfoxides	p. 109
Analysis of Lactones	p. 110
Analysis of Lactams	p. 111
Analysis of Oxaziridines	p. 112
Analysis of Axial Chiral Compounds	p. 112
Analysis of Compounds that are Chiral by Virtue of Slow Rotation	p. 113
Analysis of Metal Complexes	p. 115
Analysis of Cyclophosphazenes	p. 116
Analysis of Phosphine Oxides	p. 117
Analysis of Calixarenes	p. 118
Analysis of Other Substrates	p. 119
Use of Lanthanide Chelates with TFPE and TFAE	p. 122
Use as a Chiral Derivatizing Agent	p. 123
Other Anthryl-based Reagents	p. 123
Analogs of TFAE	p. 123
Ethyl-2-(9-anthryl)-2-hydroxyacetate	p. 126
2-(2,3-Anthracenedicarboximido)-1-cyclohexanol	p. 127
2,2,2-Trifluoro-1-(1-pyrenyl)ethanol	p. 127
2-(Trifluoromethyl)benzhydrol	p. 127
1-Phenylethanol	p. 128
Methyl Mandelate (MM)	p. 129
Octahydro-8,9,9-trimethyl-5,8-methano-2H-1-benzopuran-2-ol (Noe's Reagent)	p. 130
Menthol	p. 132
Borneol	p. 135
(-)-10-Mercaptoisoborneol	p. 135
(R)-(-)-Pantolactone	p. 136
Trans-Bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane	p. 136
2-Hydroxymethyl-4,6-dimethyl-2-phenyl-1,3-dioxane	p. 137
2-Butanol	p. 137
Assignment of Absolute Configuration Using Glycosidation Shifts	p. 138
Analysis of Di-and Polysaccharides	p. 141
[beta]-D- and [beta]-L-Fucofuranoside/Arabinofuranoside	p. 142
Linear Dextrins	p. 144
Axial Chiral (Atropoisomeric) Alcohols	p. 144
2,2[prime]-Dihydroxy-1,1[prime]-binaphthalene (BINOL)	p. 145
8,8[prime]-Dihydroxy-1,1[prime]-binaphthalene	p. 147
Alkyl-Substituted Binaphthols	p. 147
2[prime]-Hydroxy-1,1[prime]-binaphthyl-2-yl[(3,5-dinitrobenzoyl) amino](phenyl)acetate	p. 148
1,6-Di(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol	p. 148
4,4[prime]6,6[prime]-Tetrachloro-2,2[prime]-bis(hydroxydiphenylmethyl) biphenyl	p. 148
Diol and Dithiol Reagents	p. 149
Butane-2,3-diol/Butane-2,3-thiol	p. 149
2,2-Dimethyl-1,3-propanediol	p. 150
1,1,2-Triphenyl-1,2-ethanediol	p. 151
Ethylene Dithiol	p. 151
[alpha],[alpha],[alpha prime],[alpha prime]-Tetraphenyl-1,3-dioxolane-4,5-dimethanols) (TADDOL)	p. 151
Amine-based Reagents	p. 153
Primary Amines	p. 154
1-Phenylethylamine (PEA)/1-(1 -Naphthyl)ethylamine (NEA)/1-(9-Anthryl)ethylamine(AEA)	p. 154
Fluorinated Aryl Amines	p. 161
9-(1-Amino-2,2-dimethylpropyl)-9,10 dihydroanthracene	p. 161
(1S,2S)-1-Phenyl-2-amino-3-methoxy-1-propanol	p. 162
Phenylglycinol	p. 163
1-(3-Aminopropyl)-(5R,8S,10R)terguride	p. 163
5-Amino-4-aryl-2,2-dimethyl-1,3-dioxans	p. 164
Amino Acids	p. 164
Peptides	p. 164
Phenylglycine methyl ester (PGME)/Phenylglycine dimethyl-amide	p. 165
L-Cysteine	p. 168
L-Proline	p. 169
(1R,2R)-1-(1[prime],8[prime]-Naphthalimide)-2-aminocyclohexane Derivatives	p. 169
1-(1-Naphthyl)-2,2-dimethylpropylamine	p. 170
1-Methoxy-2-aminopropane	p. 170
(+)-2-Amino-1-methoxymenth-8-ene	p. 171
Secondary Amines	p. 171
Ephedrine	p. 171
2-Methyl Piperidine	p. 173
(N-Methyl)-[alpha]-isosparteinium cation	p. 174
N-Boc-1-(1-naphthyl)ethylamine	p. 174
N-Methyl-D-(-)-glucamine	p. 175
(S)-2-(Diphenylmethyl)pyrrolidine	p. 175
Tertiary Amines	p. 175
Quinine/Cinchonidine/Quinidine	p. 175
2,8-Dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5] diazocine (Troger's Base)	p. 180
Brucine	p. 180
Strychnine	p. 181
(R)- and (S)-Tetrahydroisoquinoline	p. 181
Diamine Reagents	p. 182
1,2-Diphenyl-1,2-diaminoethane	p. 182
N,N[prime]-Substituted 1,2-diphenyl-1,2-diaminoethane	p. 183
Databases Using Amine Chiral Solvating Agents	p. 184
N,[alpha]-Dimethylbenzylamine (DMBA)	p. 184
Bis-1,3-methylbenzylamine-2-methylpropane (BMBA-pMe)	p. 187
(R-[alpha]-Methoxy-[alpha]-trifluoromethylphenylacetic Acid (MTPA)/BMBA-pMe	p. 189
Miscellaneous Organic-based Chiral Derivatizing and Solvating Agents	p. 190
Amides	p. 191
N-(3,5-Dinitrobenzoyl)-1-phenylethylamine (DNB-PEA)	p. 191
N-(3,5-Dinitrobenzoyl)-L-leucine (DNB-Leu)	p. 193
N-(3,5-Dinitrobenzoyl)phenylglycine	p. 195
N-(3,5-Dinitrobenzoyl)-4-amino-3-methyl-1,2,3,4-tetrahydrophenanthrene (Whelk-O-1)	p. 195
N-1-(1-Naphthyl)ethyltrifluoroacetamide	p. 196
1-(1-Naphthyl)ethyl Urea Derivatives of Amino Acids (NEU-AA)	p. 197
Bis Allyl Amide Derivatives	p. 198
N,N[prime]-Diallyl-L-tartardiamide bis(4-tert-butylbenzoate)	p. 198
(S,S)-trans-Acenaphthene-1,2-dicarboxylic acid bis allylamide	p. 198
(R)-Phenylglycinol-N-3,5-dinitrobenzoyl-O-triethoxysilylpropylcarbamate	p. 198
N-Methyl Amide of (R)-N-Acetyl-4-methoxy Phenyl Glycine	p. 199
N-(n-Butylamide) of (S)-2-Phenylcarbamoyloxypropionic Acid	p. 199
2,2[prime]-Oxybis[N-(1-phenylethyl)acetamide]	p. 200
Tetrapeptide Species	p. 200
Tetraamidic Selector	p. 200
Lactams	p. 201
Dihydropyrimidone	p. 202
Amino Acid Isocyanurate Derivatives	p. 202
Aldehydes	p. 203
15-Formyl-14-hydroxy-2,8-dithia[9](2,5) pyridinophane	p. 203
2[prime]-Methoxy-1,1[prime]-binaphthalene-8-carbaldehyde	p. 203
2-Hydroxy-2[prime]-nitrobenzoate-3-aldehyde-1,1[prime]-binaphthalene	p. 204
2-Hydroxy-2[prime]-substituted-3-aldehyde-1,1[prime]-binaphthalene	p. 205
Ketones	p. 205
1-Menthone	p. 205
(S)-(+)-2-Propylcyclohexanone	p. 206
Isocyanates	p. 206
1-Phenylethyl Isocyanate (PE-I)	p. 206
1-(1-Naphthyl)ethy] Isocyanate (NE-I)	p. 208
Phenylethy Isothiocyanate (PE-IS)/Naphthylethyl Isothiocyanate (NE-IS)	p. 209
[alpha]-Methoxy-[alpha]-(trifluoromethyl)benzyl Isocyanate	p. 210
2,3,4,6-Tetra-O-acetyl-[beta]-D-glucopyranosyl Isothiocyanate	p. 210
(S)-2-Chloro-2-fluoroethanoyl Isocyanate	p. 211
Miscellaneous Reagents	p. 211
2,2-Dimethoxypropane	p. 211
(-)-Chloromethylmenthyl Ether	p. 212
2-Oxazolidones	p. 213
5(R)-Methyl-1-(chloromethyl)-2-pyrrolidinone	p. 214
5-Methyl-5-phenylpyrroline N-oxide	p. 215
(S)-2[(R)-Fluoro(phenyl)methyl]oxirane	p. 215
(S)-Triazine Selector	p. 216
2-Deuterio-2,3-dihydro-2-methyl-6-nitrobenzothiophene-1 -oxide	p. 216
3a-Benzhydryl-3,3a,4,5-tetrahydro-2H-cyclopenta[b]furan	p. 217
Camphor-10-sulfonic Acid (CSA)	p. 217
Menthyl Chloroformate	p. 219
(N-Methylphenylsulfoximidoyl)methyl Lithium	p. 220
Coumarin Dimer	p. 221
Di-O-benzoyl Tartrate/Di-O-p-toluoyl Tartrate	p. 221
Dibenzoyl-L-tartaric Acid Anhydride	p. 222
DNA	p. 223
5,8-Bis(aminomethyl)-1,12-dimethylbenzo[c] phenanthrene	p. 223
2[prime]-Methoxy-1,1[prime]-binaphthalene-2-carbohydroxymoyl Chloride (MBCC)	p. 223
Self-discrimination of Chiral Compounds	p. 224
High-throughput Optical Purity Measurements	p. 227
Reagents Incorporating Phosphorus, Selenium, Boron, and Silicon Atoms	p. 229
Phosphorus-containing Reagents	p. 230
Phosphorus(V) Reagents	p. 230
Phosphinic Amides (Phos1)	p. 230
Phosphinothioic Acids (Phos2)	p. 231
Cis-2-Chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazophospholidin-2-one (Phos3)	p. 234
(2-Chloro-4(R),5(R)-dimethyl-2-oxo-1,3,2-dioxaphospholane (Phos4)	p. 236
L-Menthylphenylchlorophosphine Oxide (Phos5)	p. 236
2-Chloro-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane-2-oxide (Phos6)	p. 236
O,O-Di-(2-(S)-(N,N-diethyl-2-hydroxypropyl) phosphonate (Phos7)	p. 237
2-Chloro-3-phenyl-1,3,2-diazaphosphabicyclo [3.3.0]octane-2-oxide (Phos8)	p. 238
Methyl Phosphonic Dichloride (Phos9)/Methyl Phosphonothioic Dichloride (Phos10)	p. 239
O,O-Diphenyldithioic Acid (Phos11)	p. 239
1,1[prime]-Binaphthyl-2,2[prime]-diylphosphoric Acid (Phos12)	p. 240
Phosphorus(III) Reagents	p. 242
Diazaphospholidines (Phos13-Phos20)	p. 242
1,3,2-Dioxaphospholanes (Phos21-Phos27)	p. 246
Dimenthyl Chlorophosphite (Phos28)	p. 248
Dichloromenthylphosphine (Phos29)	p. 248
Phosphorus Trichloride (Phos30)	p. 249
Hexaalkylphosphorus Triamides (Phos31)	p. 249
[alpha]-1-Phenylethylamino Trisaminoamine (Phos32)	p. 249
[5] HELOL Phosphite (Phos33)	p. 249
Ionic Reagents-TRISPHAT, BINPHAT, and BINTROP	p. 250
Configurational Analysis of Phosphates	p. 260
Oxygen Isotope Methods	p. 260
ROESY Studies	p. 263
Summary	p. 264
Selenium-containing Reagents	p. 264
4-Methyl-5-phenyloxazolidine-2-selone	p. 264
(R,R)-N,N[prime]-Dimethylcyclohexyl-1,2-diazaselenophospholine	p. 266
2-Phenylselenopropionic Acid	p. 267
1,2,3-Selenadiazoles	p. 267
Boron-containing Reagents	p. 268
2-(1-Methoxyethyl)phenylboronic Acid	p. 268
Phenylboronic Acid	p. 269
Boric Acid [B(OH)[subscript 3]]	p. 270
Camphanylboronic Acid	p. 270
4S,5R-4-Methyl-5-phenyl-1,3,2-oxazaborolidine (Ephedrine Borane)	p. 271
(S)-(+)-N-Acetylphenylglycine Boronic Acid	p. 271
1-Benzamido-1-(2-methylphenyl)methaneboronic Acid	p. 271
2-Formylphenylboronic Acid	p. 272
2,2[prime]-(1,2-Phenylene)bis(4R,5R)-4,5-diphenyl-1,3,2-dioxaborolane	p. 272
(1-Chloroalkyl)boronates	p. 273
Silyl-containing Reagents	p. 274
Menthylphenylsilylacetic Acid	p. 274
(Benzylmethylphenylsilyl)methylamine	p. 274
Monochlorosilanes	p. 275
Host Compounds as Chiral NMR Discriminating Agents	p. 278
Cyclodextrins	p. 279
Introduction	p. 279
Native Cyclodextrins	p. 280
Lanthanide Coupling to Native Cyclodextrins	p. 286
Neutral Cyclodextrin Derivatives	p. 287
Hexakis(2,3,6-tri-O-methyl)-[alpha]-cyclodextrin (TM-[alpha]-CD)/Heptakis(2,3,6-tri-O-methyl)-[beta]-cyclodextrin (TM-[beta]-CD) - (Permethyl CDs)	p. 287
Heptakis(2,6-di-O-methyl)-[beta]-cyclodextrin (2,6-DM-[beta]-CD)	p. 289
Benzylated and Benzoylated Cyclodextrins	p. 290
Carbamoylated Cyclodextrins	p. 290
Octakis(3-O-butanoyl-2,6-di-O-pentyl)-[gamma]-cyclodextrin (BP-CD)	p. 291
Hydroxyethyl and Hydroxypropyl Cyclodextrins (HE-CD, HP-CD)	p. 291
Heptakis(2,3-di-O-acetyl)-[beta]-C D(2,3-DA-[beta]-CD)	p. 291
Mono(2-acetylamino-2-deoxy)-, Mono (3-acetylamino-3-deoxy)- and Mono (6-acetylamino-6-deoxy)-[beta]-cyclodextrin (AA-[beta]-CD)	p. 292
Mono-3,6-anhydro-[beta]-cyclodextrin	p. 292
Heptakis(3-O-acetyl-2,6-di-O-pentyl)-[beta]-cyclodextrin	p. 292
Octakis(2,6-di-O-pentyl-3-O-trifluoroacetyl)-[gamma]-cyclodextrin	p. 292
Cyanoethylated-[beta]-cyclodextrin	p. 292
Per-O-octyl-[alpha]-cyclodextrin	p. 293
Biphenyl-capped-[beta]-cyclodextrin	p. 293
Heptakis(2,3,6-tri-O-acetyl)-[beta]-CD (TA-[beta]-CD)	p. 293
Anionic Cyclodextrin Derivatives	p. 293
Carboxymethylated Cyclodextrins (CM-CD)	p. 293
Heptakis(6-carboxymethylthio-6-deoxy)-[beta]-cyclodextrin (6-CMT-[beta]-CD)	p. 296
Sulfobutylether-[beta]-cyclodextrin (SBE-[beta]-CD)	p. 296
Heptakis(2,3-di-O-acetyl-6-sulfo)-[beta]-CD (HDAS-[beta]-CD)	p. 297
Sulfated Cyclodextrins (S-CD)	p. 298
Cationic Cyclodextrin Derivatives	p. 298
Amino-substituted Cyclodextrins	p. 298
Bis(6-trimethylammonio)-[beta]-cyclodextrin (TMA-[beta]-CD)	p. 299
Mono(6-xylylenediamine)-[beta]-cyclodextrin (X-[beta]-CD)	p. 299
Summary	p. 299
Crown Ethers	p. 300
Introduction	p. 300
(18-Crown-6)-2,3,11,12-tetracarboxylic Acid (18-C-6-TCA)	p. 301
Amide Derivatives of (18-Crown-6)-2,3,11,12-tetracarboxylic Acid	p. 303
(18-Crown-6)-2,3,11,12-derivatives	p. 303
Crown Ethers Incorporating a 2,2[prime]-Dihydroxy-1,1[prime]-binaphthalene Unit	p. 305
Glycoside-derived Crown Ethers	p. 305
Crown Ether-like Compounds with Nitrogen-heterocyclic Units	p. 306
Triazole-18-crown-6 Ether	p. 308
Crown Ether-like Compounds with Phenol Units	p. 308
Aza Crown Ethers	p. 309
Calixarenes and Calixresorcarenes	p. 311
Introduction	p. 311
Calix[4]resorcarenes	p. 312
Calixarenes	p. 315
Summary	p. 319
Receptor Compounds for Carboxylic Acids	p. 320
Cyclic Peptides	p. 323
Miscellaneous Receptor Compounds	p. 324
Cyclic Tetraamidic Reagent	p. 324
Cyclosophoraoses (Cyclic(1-2)-[beta]-D-glucans)	p. 325
Glycophane Receptor	p. 325
Cyclophane Receptors	p. 326
Cryptophane Receptor	p. 326
Receptor for Secondary Amines	p. 327
Spirobisindane Receptor	p. 327
Receptors for Diols	p. 328
1,1[prime]-Binaphthalene-based Receptors	p. 328
Enzymes	p. 329
Calmodulin	p. 329
Chymotrypsin	p. 330
Chiral Discrimination with Metal-based Reagents	p. 331
Introduction	p. 331
Lanthanide Complexes	p. 332
Introduction	p. 332
Peak Broadening with Lanthanide Shift Reagents	p. 335
Catalytic Properties of Lanthanide Ions	p. 337
Application of Lanthanide tris [beta]-diketonates	p. 338
Discrimination of Prochiral Nuclei	p. 339
Analysis of Deuterium-Substituted Compounds	p. 341
Analysis of Compounds Chiral by Virtue of Slow Rotation	p. 342
Analysis of Compounds Chiral by Virtue of Geometrical Constraints	p. 344
Miscellaneous Applications of Lanthanide tris [beta]-diketonates	p. 346
Analysis of Chiral Metal Complexes	p. 348
Assignment of Absolute Stereochemistry	p. 351
Pr(III) Complex of Tetraphenylimidodiphosphinate-Pr(tpip)[subscript 3]	p. 354
Binuclear Lanthanide-silver Reagents	p. 355
Analysis of Organic Salts	p. 358
Aqueous Lanthanide Shift Reagents	p. 359
Complexes of Propylenediaminetetraacetate (pdta)	p. 360
Complexes of N,N,N[prime],N[prime]-Tetrakis(pyridylmethyl) propylene Diamine (TPPN)	p. 361
Complexes with Other Ligands	p. 362
Complexes with Tetraazocyclodecane Macrocyclic Ligands	p. 364
Transition Metal Complexes	p. 365
Palladium Complexes	p. 365
Bridged Dimers with Amine Ligands	p. 365
Miscellaneous Palladium Complexes	p. 372
Platinum Complexes	p. 374
Complexes with Diphosphine Ligands	p. 374
Complexes with Amine Ligands	p. 375
Analysis of Geometrical Isomers	p. 378
Rhodium Complexes	p. 378
Rhodium Dimer-[Rh[subscript 2](MTPA)[subscript 4]]	p. 378
Miscellaneous Rhodium Complexes	p. 384
Cobalt Complexes	p. 385
Complexes with Porphyrin Ligands	p. 385
Analysis of Geometrical Isomers	p. 387
Analysis of DNA	p. 389
Zinc Complexes	p. 389
Ruthenium Complexes	p. 392
Nickel Complexes	p. 394
Copper Complexes	p. 394
Silver Complexes	p. 395
Tin Complexes	p. 396
Titanium Complexes	p. 397
Tungsten Complexes	p. 397
Molybdenum Complexes	p. 397
Mercury Complexes	p. 397
Osmium Complexes	p. 398
Uranium Complexes	p. 398
Chiral NMR Discrimination with Highly Ordered Systems	p. 399
Introduction	p. 399
Liquid Crystals	p. 400
Introduction	p. 400
Early Studies with Liquid Crystals	p. 401
[superscript 2]H NMR Analysis of Labeled Compounds	p. 403
Natural Abundance [superscript 2]H NMR Analysis	p. 410
[superscript 13]C NMR Analysis	p. 412
[superscript 1]H NMR Analysis	p. 414
[superscript 19]F NMR Analysis	p. 414
Analysis Using Other Nuclei	p. 415
Miscellaneous Studies with Liquid Crystals	p. 415
Micelles and Gels	p. 416
Ionic Liquids	p. 419
Polymers	p. 420
Cellulose-carbamate Polymers	p. 420
Poly 3- and 4-((S-([alpha]-Methylbenzylcarbamoyl) phenyl Isocyanate	p. 421
Poly(ester[beta]-sulfoxides)	p. 421
Chirasil-val	p. 422
Poly(N-1-anthrylmaleimide)	p. 422
Poly [(1-6)-2,5-anhydro-3,4-di-O-methyl-D-glucitol]	p. 423
Aggregation of Achiral Compounds into Chiral Assemblies	p. 423
Solid-state NMR Spectroscopy	p. 425
Tri-O-thymotide Clathrates	p. 425
Cholic Acid Channels	p. 426
Analysis of Polymer-bound Compounds	p. 427
References	p. 428
Index	p. 537
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Discrimination of Chiral Compounds Using NMR Spectroscopy

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