Catalogue


Discrimination of chiral compounds using NMR spectroscopy /
Thomas J. Wenzel.
imprint
Hoboken, N.J. : Wiley-Interscience, c2007.
description
xxiii, 549 p.
ISBN
0471763527 (alk. paper), 9780471763529 (alk. paper)
format(s)
Book
Holdings
More Details
imprint
Hoboken, N.J. : Wiley-Interscience, c2007.
isbn
0471763527 (alk. paper)
9780471763529 (alk. paper)
catalogue key
6142982
 
Includes bibliographical references (p. 428-535) and index.
A Look Inside
About the Author
Author Affiliation
Thomas J. Wenzel is the Charles A. Dana Professor of Chemistry at Bates College in Lewiston, Maine.
Reviews
Review Quotes
"...a foremost literature resource for NMR-based enantiodiscrimination." ( Journal of Medicinal Chemistry , October 18, 2007)
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SciTech Book News, September 2007
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Summaries
Main Description
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.
Back Cover Copy
A comprehensive overview of the use of NMR spectroscopy for chiral discriminationDiscrimination 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 reportedCatalogs the range of compounds for which different reagents have been shown to be effectiveIncludes 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 categoriesOffers experimental strategies for using the reagents that are likely to improve the quality of the resultsThis 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.
Bowker Data Service Summary
Providing NMR methods for determination of molecular chirality, this book focuses on commercially available systems. Wenzel catalogs the range of compounds for which different reagents have been shown to be effective.
Back Cover Copy
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.
Table of Contents
Prefacep. xxi
Acknowledgmentsp. xxiii
Introductionp. 1
Chiral Derivatizing Agentsp. 1
Chiral Solvating Agentsp. 2
Overview of Chiral Reagents and Methodologiesp. 4
Future Prospectsp. 6
Aryl-Containing Carboxylic Addsp. 8
Introductionp. 8
[alpha]-Methoxy-[alpha]-trifluoromethylphenylacetic Acid (MTPA-Mosher's Reagent)p. 11
Analysis of Secondary Alcoholsp. 13
Analysis of Secondary Diols and Polyolsp. 19
Analysis of Primary Alcoholsp. 25
Analysis of Tertiary Alcoholsp. 26
Analysis of Secondary Aminesp. 26
Analysis of Primary Aminesp. 28
Use as a Chiral Solvating Agentp. 29
Use of MTPA Derivatives with Paramagnetic Lanthanide Chelatesp. 30
Use of MTPA Derivatives with Diamagnetic Lanthanide Chelatesp. 34
Preparation of MTPA Derivativesp. 35
Liquid Chromatography-NMR Spectroscopy of MTPA Derivativesp. 35
Database Methods with MTPAp. 35
[alpha]-Methoxyphenylacetic Acid (O-methyl Mandelic Acid-MPA)p. 38
Analysis of Secondary Alcoholsp. 39
Analysis of Diolsp. 42
Analysis of Primary Alcoholsp. 43
Analysis of Aminesp. 44
Analysis of Sulfoxidesp. 45
Variable-temperature Method for Assigning Absolute Stereochemistryp. 46
Barium(II) Method for Assigning Absolute Stereochemistryp. 47
Use of MPA Derivatives with Lanthanide Chelatesp. 48
Use as a Chiral Solvating Agentp. 49
Preparation of MPA Derivatives-The "Mix and Shake" Methodp. 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 Acidp. 56
2-Phenylpropionic Acid (2-PPA)p. 57
2-Methoxy-2-phenylpropionic Acidp. 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 Derivativesp. 63
N-(5-Fluoro-2,4-dinitrophenyl)-1-phenylethylamidep. 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 Acidp. 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 Acidp. 70
2-Methoxy-2-(1-naphthyl) Propionic Acid (M[alpha]NP)p. 71
1-Methoxy-2,3-dihydro-1H-cyclopenta[a]naphthalene-1-carboxylic Acidp. 72
O-Aryl Lactic Acidsp. 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 Acidp. 78
2-Methoxy-2-(9-phenanthryl)propionic Acidp. 78
Summaryp. 79
Analysis of Primary Alcoholsp. 79
Analysis of Secondary Alcoholsp. 79
Analysis of Tertiary Alcoholsp. 80
Analysis of Primary Aminesp. 80
Analysis of Secondary Aminesp. 81
Other Carboxylic Acid-based Reagentsp. 82
Camphanic Acidp. 82
Menthoxyacetic Acid (MAA)p. 86
2-(2,3-Anthracenedicarboximido)cyclohexane Carboxylic Acidp. 87
3[beta]-Acetoxy-[Delta]5-etiocholenic Acidp. 88
Naproxenp. 89
2-tert-Butyl-2-methyl-1,3-benzodioxole-4-carboxylic Acidp. 90
Endo-3-Benzamidonorbornane-2-carboxylic Acidp. 90
Coumarin-based Reagentsp. 91
2,2-Diphenylcyclopropane Carboxylic Acidp. 91
Amide Derivatives of Kemp's Triacidp. 91
Amino Acidsp. 92
N-Boc-phenylalaninep. 92
Isotopically Substituted Amino Acidsp. 92
(R)-(-)-(2,3,5,7-Tetranitro-9-fluorenyloximino)propanoic Acidp. 93
2-Chloropropanoic Acid (2-C1-PA)p. 93
Chlorofluoroacetic Acidp. 94
Perfluoropropoxy Propionic Acid/Perfluoro Isopropropoxy Propionic Acidp. 94
2-Methylbutyric Acidp. 94
Lactic Acid and Derivativesp. 95
Trifluorolactic Acidp. 95
(S)-O-Acetyllactylchloridep. 95
Lasalocidp. 96
Axial Chiral Carboxylic Acidsp. 96
(+)-1-[2-Carboxy-6-(trifluoromethyl)phenyl]pyrrole-2-carboxylic Acidp. 96
2[prime]-Methoxy-1,1[prime]-binaphthyl-2-carboxylic Acid (MBNC)p. 97
2[prime]-Methoxy-1,1[prime]-binaphthalene-8-carboxylic Acidp. 98
2[prime]-Octylcarbamoyl-1,1[prime]-binaphthyl-2-dicarboxylic Acidp. 100
2-(2[prime]-Methoxy-1[prime]-naphthyl)-3,5-dichlorobenzoic Acid (MNCB)p. 100
Hydroxyl-and Thiol-Containing Reagentsp. 102
2,2,2-Trifluorophenylethanol (TFPE)p. 103
2,2,2-Trifluoro-1-(9-anthryl)ethanol (Pirkle's Alcohol (TFAE)p. 109
Analysis of Sulfoxidesp. 109
Analysis of Lactonesp. 110
Analysis of Lactamsp. 111
Analysis of Oxaziridinesp. 112
Analysis of Axial Chiral Compoundsp. 112
Analysis of Compounds that are Chiral by Virtue of Slow Rotationp. 113
Analysis of Metal Complexesp. 115
Analysis of Cyclophosphazenesp. 116
Analysis of Phosphine Oxidesp. 117
Analysis of Calixarenesp. 118
Analysis of Other Substratesp. 119
Use of Lanthanide Chelates with TFPE and TFAEp. 122
Use as a Chiral Derivatizing Agentp. 123
Other Anthryl-based Reagentsp. 123
Analogs of TFAEp. 123
Ethyl-2-(9-anthryl)-2-hydroxyacetatep. 126
2-(2,3-Anthracenedicarboximido)-1-cyclohexanolp. 127
2,2,2-Trifluoro-1-(1-pyrenyl)ethanolp. 127
2-(Trifluoromethyl)benzhydrolp. 127
1-Phenylethanolp. 128
Methyl Mandelate (MM)p. 129
Octahydro-8,9,9-trimethyl-5,8-methano-2H-1-benzopuran-2-ol (Noe's Reagent)p. 130
Mentholp. 132
Borneolp. 135
(-)-10-Mercaptoisoborneolp. 135
(R)-(-)-Pantolactonep. 136
Trans-Bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentanep. 136
2-Hydroxymethyl-4,6-dimethyl-2-phenyl-1,3-dioxanep. 137
2-Butanolp. 137
Assignment of Absolute Configuration Using Glycosidation Shiftsp. 138
Analysis of Di-and Polysaccharidesp. 141
[beta]-D- and [beta]-L-Fucofuranoside/Arabinofuranosidep. 142
Linear Dextrinsp. 144
Axial Chiral (Atropoisomeric) Alcoholsp. 144
2,2[prime]-Dihydroxy-1,1[prime]-binaphthalene (BINOL)p. 145
8,8[prime]-Dihydroxy-1,1[prime]-binaphthalenep. 147
Alkyl-Substituted Binaphtholsp. 147
2[prime]-Hydroxy-1,1[prime]-binaphthyl-2-yl[(3,5-dinitrobenzoyl) amino](phenyl)acetatep. 148
1,6-Di(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diolp. 148
4,4[prime]6,6[prime]-Tetrachloro-2,2[prime]-bis(hydroxydiphenylmethyl) biphenylp. 148
Diol and Dithiol Reagentsp. 149
Butane-2,3-diol/Butane-2,3-thiolp. 149
2,2-Dimethyl-1,3-propanediolp. 150
1,1,2-Triphenyl-1,2-ethanediolp. 151
Ethylene Dithiolp. 151
[alpha],[alpha],[alpha prime],[alpha prime]-Tetraphenyl-1,3-dioxolane-4,5-dimethanols) (TADDOL)p. 151
Amine-based Reagentsp. 153
Primary Aminesp. 154
1-Phenylethylamine (PEA)/1-(1 -Naphthyl)ethylamine (NEA)/1-(9-Anthryl)ethylamine(AEA)p. 154
Fluorinated Aryl Aminesp. 161
9-(1-Amino-2,2-dimethylpropyl)-9,10 dihydroanthracenep. 161
(1S,2S)-1-Phenyl-2-amino-3-methoxy-1-propanolp. 162
Phenylglycinolp. 163
1-(3-Aminopropyl)-(5R,8S,10R)terguridep. 163
5-Amino-4-aryl-2,2-dimethyl-1,3-dioxansp. 164
Amino Acidsp. 164
Peptidesp. 164
Phenylglycine methyl ester (PGME)/Phenylglycine dimethyl-amidep. 165
L-Cysteinep. 168
L-Prolinep. 169
(1R,2R)-1-(1[prime],8[prime]-Naphthalimide)-2-aminocyclohexane Derivativesp. 169
1-(1-Naphthyl)-2,2-dimethylpropylaminep. 170
1-Methoxy-2-aminopropanep. 170
(+)-2-Amino-1-methoxymenth-8-enep. 171
Secondary Aminesp. 171
Ephedrinep. 171
2-Methyl Piperidinep. 173
(N-Methyl)-[alpha]-isosparteinium cationp. 174
N-Boc-1-(1-naphthyl)ethylaminep. 174
N-Methyl-D-(-)-glucaminep. 175
(S)-2-(Diphenylmethyl)pyrrolidinep. 175
Tertiary Aminesp. 175
Quinine/Cinchonidine/Quinidinep. 175
2,8-Dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5] diazocine (Troger's Base)p. 180
Brucinep. 180
Strychninep. 181
(R)- and (S)-Tetrahydroisoquinolinep. 181
Diamine Reagentsp. 182
1,2-Diphenyl-1,2-diaminoethanep. 182
N,N[prime]-Substituted 1,2-diphenyl-1,2-diaminoethanep. 183
Databases Using Amine Chiral Solvating Agentsp. 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-pMep. 189
Miscellaneous Organic-based Chiral Derivatizing and Solvating Agentsp. 190
Amidesp. 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)phenylglycinep. 195
N-(3,5-Dinitrobenzoyl)-4-amino-3-methyl-1,2,3,4-tetrahydrophenanthrene (Whelk-O-1)p. 195
N-1-(1-Naphthyl)ethyltrifluoroacetamidep. 196
1-(1-Naphthyl)ethyl Urea Derivatives of Amino Acids (NEU-AA)p. 197
Bis Allyl Amide Derivativesp. 198
N,N[prime]-Diallyl-L-tartardiamide bis(4-tert-butylbenzoate)p. 198
(S,S)-trans-Acenaphthene-1,2-dicarboxylic acid bis allylamidep. 198
(R)-Phenylglycinol-N-3,5-dinitrobenzoyl-O-triethoxysilylpropylcarbamatep. 198
N-Methyl Amide of (R)-N-Acetyl-4-methoxy Phenyl Glycinep. 199
N-(n-Butylamide) of (S)-2-Phenylcarbamoyloxypropionic Acidp. 199
2,2[prime]-Oxybis[N-(1-phenylethyl)acetamide]p. 200
Tetrapeptide Speciesp. 200
Tetraamidic Selectorp. 200
Lactamsp. 201
Dihydropyrimidonep. 202
Amino Acid Isocyanurate Derivativesp. 202
Aldehydesp. 203
15-Formyl-14-hydroxy-2,8-dithia[9](2,5) pyridinophanep. 203
2[prime]-Methoxy-1,1[prime]-binaphthalene-8-carbaldehydep. 203
2-Hydroxy-2[prime]-nitrobenzoate-3-aldehyde-1,1[prime]-binaphthalenep. 204
2-Hydroxy-2[prime]-substituted-3-aldehyde-1,1[prime]-binaphthalenep. 205
Ketonesp. 205
1-Menthonep. 205
(S)-(+)-2-Propylcyclohexanonep. 206
Isocyanatesp. 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 Isocyanatep. 210
2,3,4,6-Tetra-O-acetyl-[beta]-D-glucopyranosyl Isothiocyanatep. 210
(S)-2-Chloro-2-fluoroethanoyl Isocyanatep. 211
Miscellaneous Reagentsp. 211
2,2-Dimethoxypropanep. 211
(-)-Chloromethylmenthyl Etherp. 212
2-Oxazolidonesp. 213
5(R)-Methyl-1-(chloromethyl)-2-pyrrolidinonep. 214
5-Methyl-5-phenylpyrroline N-oxidep. 215
(S)-2[(R)-Fluoro(phenyl)methyl]oxiranep. 215
(S)-Triazine Selectorp. 216
2-Deuterio-2,3-dihydro-2-methyl-6-nitrobenzothiophene-1 -oxidep. 216
3a-Benzhydryl-3,3a,4,5-tetrahydro-2H-cyclopenta[b]furanp. 217
Camphor-10-sulfonic Acid (CSA)p. 217
Menthyl Chloroformatep. 219
(N-Methylphenylsulfoximidoyl)methyl Lithiump. 220
Coumarin Dimerp. 221
Di-O-benzoyl Tartrate/Di-O-p-toluoyl Tartratep. 221
Dibenzoyl-L-tartaric Acid Anhydridep. 222
DNAp. 223
5,8-Bis(aminomethyl)-1,12-dimethylbenzo[c] phenanthrenep. 223
2[prime]-Methoxy-1,1[prime]-binaphthalene-2-carbohydroxymoyl Chloride (MBCC)p. 223
Self-discrimination of Chiral Compoundsp. 224
High-throughput Optical Purity Measurementsp. 227
Reagents Incorporating Phosphorus, Selenium, Boron, and Silicon Atomsp. 229
Phosphorus-containing Reagentsp. 230
Phosphorus(V) Reagentsp. 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) Reagentsp. 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 BINTROPp. 250
Configurational Analysis of Phosphatesp. 260
Oxygen Isotope Methodsp. 260
ROESY Studiesp. 263
Summaryp. 264
Selenium-containing Reagentsp. 264
4-Methyl-5-phenyloxazolidine-2-selonep. 264
(R,R)-N,N[prime]-Dimethylcyclohexyl-1,2-diazaselenophospholinep. 266
2-Phenylselenopropionic Acidp. 267
1,2,3-Selenadiazolesp. 267
Boron-containing Reagentsp. 268
2-(1-Methoxyethyl)phenylboronic Acidp. 268
Phenylboronic Acidp. 269
Boric Acid [B(OH)[subscript 3]]p. 270
Camphanylboronic Acidp. 270
4S,5R-4-Methyl-5-phenyl-1,3,2-oxazaborolidine (Ephedrine Borane)p. 271
(S)-(+)-N-Acetylphenylglycine Boronic Acidp. 271
1-Benzamido-1-(2-methylphenyl)methaneboronic Acidp. 271
2-Formylphenylboronic Acidp. 272
2,2[prime]-(1,2-Phenylene)bis(4R,5R)-4,5-diphenyl-1,3,2-dioxaborolanep. 272
(1-Chloroalkyl)boronatesp. 273
Silyl-containing Reagentsp. 274
Menthylphenylsilylacetic Acidp. 274
(Benzylmethylphenylsilyl)methylaminep. 274
Monochlorosilanesp. 275
Host Compounds as Chiral NMR Discriminating Agentsp. 278
Cyclodextrinsp. 279
Introductionp. 279
Native Cyclodextrinsp. 280
Lanthanide Coupling to Native Cyclodextrinsp. 286
Neutral Cyclodextrin Derivativesp. 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 Cyclodextrinsp. 290
Carbamoylated Cyclodextrinsp. 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]-cyclodextrinp. 292
Heptakis(3-O-acetyl-2,6-di-O-pentyl)-[beta]-cyclodextrinp. 292
Octakis(2,6-di-O-pentyl-3-O-trifluoroacetyl)-[gamma]-cyclodextrinp. 292
Cyanoethylated-[beta]-cyclodextrinp. 292
Per-O-octyl-[alpha]-cyclodextrinp. 293
Biphenyl-capped-[beta]-cyclodextrinp. 293
Heptakis(2,3,6-tri-O-acetyl)-[beta]-CD (TA-[beta]-CD)p. 293
Anionic Cyclodextrin Derivativesp. 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 Derivativesp. 298
Amino-substituted Cyclodextrinsp. 298
Bis(6-trimethylammonio)-[beta]-cyclodextrin (TMA-[beta]-CD)p. 299
Mono(6-xylylenediamine)-[beta]-cyclodextrin (X-[beta]-CD)p. 299
Summaryp. 299
Crown Ethersp. 300
Introductionp. 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 Acidp. 303
(18-Crown-6)-2,3,11,12-derivativesp. 303
Crown Ethers Incorporating a 2,2[prime]-Dihydroxy-1,1[prime]-binaphthalene Unitp. 305
Glycoside-derived Crown Ethersp. 305
Crown Ether-like Compounds with Nitrogen-heterocyclic Unitsp. 306
Triazole-18-crown-6 Etherp. 308
Crown Ether-like Compounds with Phenol Unitsp. 308
Aza Crown Ethersp. 309
Calixarenes and Calixresorcarenesp. 311
Introductionp. 311
Calix[4]resorcarenesp. 312
Calixarenesp. 315
Summaryp. 319
Receptor Compounds for Carboxylic Acidsp. 320
Cyclic Peptidesp. 323
Miscellaneous Receptor Compoundsp. 324
Cyclic Tetraamidic Reagentp. 324
Cyclosophoraoses (Cyclic(1-2)-[beta]-D-glucans)p. 325
Glycophane Receptorp. 325
Cyclophane Receptorsp. 326
Cryptophane Receptorp. 326
Receptor for Secondary Aminesp. 327
Spirobisindane Receptorp. 327
Receptors for Diolsp. 328
1,1[prime]-Binaphthalene-based Receptorsp. 328
Enzymesp. 329
Calmodulinp. 329
Chymotrypsinp. 330
Chiral Discrimination with Metal-based Reagentsp. 331
Introductionp. 331
Lanthanide Complexesp. 332
Introductionp. 332
Peak Broadening with Lanthanide Shift Reagentsp. 335
Catalytic Properties of Lanthanide Ionsp. 337
Application of Lanthanide tris [beta]-diketonatesp. 338
Discrimination of Prochiral Nucleip. 339
Analysis of Deuterium-Substituted Compoundsp. 341
Analysis of Compounds Chiral by Virtue of Slow Rotationp. 342
Analysis of Compounds Chiral by Virtue of Geometrical Constraintsp. 344
Miscellaneous Applications of Lanthanide tris [beta]-diketonatesp. 346
Analysis of Chiral Metal Complexesp. 348
Assignment of Absolute Stereochemistryp. 351
Pr(III) Complex of Tetraphenylimidodiphosphinate-Pr(tpip)[subscript 3]p. 354
Binuclear Lanthanide-silver Reagentsp. 355
Analysis of Organic Saltsp. 358
Aqueous Lanthanide Shift Reagentsp. 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 Ligandsp. 362
Complexes with Tetraazocyclodecane Macrocyclic Ligandsp. 364
Transition Metal Complexesp. 365
Palladium Complexesp. 365
Bridged Dimers with Amine Ligandsp. 365
Miscellaneous Palladium Complexesp. 372
Platinum Complexesp. 374
Complexes with Diphosphine Ligandsp. 374
Complexes with Amine Ligandsp. 375
Analysis of Geometrical Isomersp. 378
Rhodium Complexesp. 378
Rhodium Dimer-[Rh[subscript 2](MTPA)[subscript 4]]p. 378
Miscellaneous Rhodium Complexesp. 384
Cobalt Complexesp. 385
Complexes with Porphyrin Ligandsp. 385
Analysis of Geometrical Isomersp. 387
Analysis of DNAp. 389
Zinc Complexesp. 389
Ruthenium Complexesp. 392
Nickel Complexesp. 394
Copper Complexesp. 394
Silver Complexesp. 395
Tin Complexesp. 396
Titanium Complexesp. 397
Tungsten Complexesp. 397
Molybdenum Complexesp. 397
Mercury Complexesp. 397
Osmium Complexesp. 398
Uranium Complexesp. 398
Chiral NMR Discrimination with Highly Ordered Systemsp. 399
Introductionp. 399
Liquid Crystalsp. 400
Introductionp. 400
Early Studies with Liquid Crystalsp. 401
[superscript 2]H NMR Analysis of Labeled Compoundsp. 403
Natural Abundance [superscript 2]H NMR Analysisp. 410
[superscript 13]C NMR Analysisp. 412
[superscript 1]H NMR Analysisp. 414
[superscript 19]F NMR Analysisp. 414
Analysis Using Other Nucleip. 415
Miscellaneous Studies with Liquid Crystalsp. 415
Micelles and Gelsp. 416
Ionic Liquidsp. 419
Polymersp. 420
Cellulose-carbamate Polymersp. 420
Poly 3- and 4-((S-([alpha]-Methylbenzylcarbamoyl) phenyl Isocyanatep. 421
Poly(ester[beta]-sulfoxides)p. 421
Chirasil-valp. 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 Assembliesp. 423
Solid-state NMR Spectroscopyp. 425
Tri-O-thymotide Clathratesp. 425
Cholic Acid Channelsp. 426
Analysis of Polymer-bound Compoundsp. 427
Referencesp. 428
Indexp. 537
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