Chiral analysis: advances in spectroscopy, chromatography and emerging methods
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Format: | Buch |
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Sprache: | English |
Veröffentlicht: |
Amsterdam
Elservier
[2018]
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Ausgabe: | Second edition |
Schlagworte: | |
Online-Zugang: | Inhaltsverzeichnis Klappentext |
Beschreibung: | xviii, 804 Seiten Illustrationen |
ISBN: | 9780444640277 |
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adam_text | CONTENTS
List of Contributors xiii
Preface xvii
Part One Chirality in Nature 1
1. Chiral Asymmetry in Nature 3
Dilip Kondepudi
1.1 Introduction 3
1.2 Chirality: terminology and quantification issues 3
1.3 Chiral asymmetry in nature 10
1.4 Theory of spontaneous chiral symmetry breaking 15
1.5 Sensitivity of chiral symmetry breaking transitions to asymmetric
interactions 19
1.6 Examples of spontaneous chiral symmetry breaking 22
1.7 Concluding remarks 25
References 25
2. Remote Sensing of Homochirality: A Proxy for the Detection
of Extraterrestrial Life 29
C.H. Lucas Patty, Inge Loes ten Kate, William B. Sparks, Frans Snik
2.1 Introduction 29
2.2 Homochirality 30
2.3 Chemical and biological mechanisms for creating circular
speciropolarimetric signals 35
2.4 Considerations for the remote sensing of homochirality in our solar
system and beyond 45
2.5 Instrumentation 50
2.6 Conclusion and outlook 60
References 61
Part Two Spectroscopic Methods and Analyses 71
3. Light Polarization and Signal Processing in Chiroptical
Instrumentation 73
Kenneth W. Busch, Marianna A. Busch
3.1 Introduction 73
Part A—The polarization of light 73
3.2 Light as a wave 74
v
VI
Contents
3.3 Types of polarized light
3.4 Production of linearly polarized light
3.5 Production of circularly polarized light
3.6 Production of elüpîically polarized light
3.7 Photoelastic modulators
Part B—Signal handling
3.8 Noise in electrical circuits
3.9 Noise reduction strategies
3.10 Application of phase-sensitive detection in chiroptical instrumentation
Appendix A basic optics
Appendix B signal handling
References
76
81
98
101
101
105
105
108
123
126
136
150
4. Chiroptical Spectroscopic Studies on Soft Aggreg ates
and Their Interactions 153
Vijay Raghavan, Prasad L. Polavarapu
4.1 Introduction 153
4.2 OR studies 158
4.3 ECD studies 172
4.4 VCD studies 184
4.5 ROA studies 193
4.6 Summary 195
References 195
5. Vibrational Optical Activity in Chiral Analysis 201
Laurence A. Ñafie, Rina K. Dukor
5.1 Introduction
5.2 Definitions of VOA
5.3 Measurement of VOA
5.4 Theoretical basis of VOA
5.5 Calculation of VOA
5.6 Determination of AC
5.7 Determination of ee of multiple chiral species
5.8 VOA of solids and formulated products
5.9 Summary and conclusions
References
201
204
206
208
214
216
226
235
238
239
6.
Raman Optical Activity
Saeideh Ostovar pour, Laurence D. Barron, Shaun T. Mutte f Ew£)n w B|anch
6.1 Fundamental principles
6.2 Experimental ROA studies
249
250
256
Contents
vii
6.3 Enhancement of ROA signals 270
6.4 Recent ROA instrumentation developments 273
6.5 Computational modeling of ROA spectra 274
6.6 Concluding remarks: future opportunities 282
References 284
7. Chiral Molecular Tools Powerful for the Preparation
of Enantiopure Compounds and Unambiguous Determination
of Their Absolute Configurations by X-Ray crystallography
and/or ’H NMR Diamagnetic Anisotropy 293
Nobuyuki Harada
7.1 Introduction 293
7.2 Methodologies for determining AC and their evaluations 294
7.3 Methodologies for chiral synthesis and their evaluations 297
7.4 Camphorsultam dichlorophthalic acid, CSDP acid (-)-!,
and camphorsultam phthalic acid, CPS acid (-9-5, useful
for enantioresolution of alcohols by HPLC and determination
of their ACs by X-ray crystallography 299
7.5 A novel chiral molecular tool, 2-methoxy-2-(1-naphthyl)-propionic
acid {MaNP acid (s)-(+)-2}, useful for enantioresolution of alcohols
and determination of their ACs by the H nmr diamagnetic anisotropy
method 312
7.6 Complementary use of CSDP acid (-)-! and MaNP acid (s)-(+)-2
for enantioresolution of alcohols and determination of their ACs
by X-ray crystallographic and H nmr diamagnetic anisotropy
methods 325
7.7 Conclusions 338
References 339
8. Chiroptical Probes for Determination of Absolute
Stereochemistry by Circular Dichroism Exciton Chirality
Method 345
Kuwahara Shunsuke, Ikeda Mari, Habata Yoichi
8.1 Introduction 345
8.2 A chiroptical probe for chiral resolution and determination
of the absolute configuration of aromatic alcohols 346
8.3 A chiroptical probe for determination of the absolute configuration
of primary amines 352
8.4 A chiroptical probe for chirality transcription and amplification
by the forming of [2]pseudorotaxanes 358
8.5 Conclusions 363
References 363
Contents
VIM
9. Chiral Analysis by NMR Spectroscopy: Chiral Solvating Agents 367
Federica Balzano, Gloria Uccello-Barretta, Federica Aiello
9.1 Introduction 367
9.2 Low-molecular-weight csas 371
9.3 CSAs involving ion pairing processes 383
9.4 Molecular tweezer csas 389
9.5 Synthetic macrocycle csas 391
9.6 Cyclodextrms 401
9.7 Natural products 406
9.8 Lyotropic chiral liquid crystals 408
9.9 Chiral sensing 409
9.10 Configurational assignments 409
9.11 Conclusions 411
References 412
10. Chiroptical Spectroscopy of Biofluids 429
Vladimir Setnicka, Lucie Habartova
10.1 Introduction 429
10.2 Blood and blood-based derivatives 430
10.3 Hen egg white 446
10.4 Vitreous humor 447
10.5 Urine 447
10.6 Chiroclinics—chiroptical methods as diagnostic tools 452
10.7 Concluding remarks 459
References 460
Part Three Chromatographic and Electromigration Methods 467
11. Chiral Gas Chromatography 469
Rahul A. Patil, Choyce A. Weatherly, Daniel W. Armstrong
11.1 Introduction 469
11.2 Commercial stationary phases 471
11.3 Non-commercial stationary phases 490
11.4 Conclusions 500
References 500
12. Chiral Liquid Chromatography 507
Muhammad F.Wahab, Choyce A. Weatherly, Rahul A. Patil,
Daniel W. Armstrong
12.1 Introduction
12.2 Historical background of chiral liquid chromatography 508
Conrents
ix
12.3 Interactions in chiral liquid chromatography 509
12.4 Chiral separations in liquid chromatography today 512
12.5 Salient features of chiral liquid chromatography 512
12.6 Major classes of modern chiral stationary phases (CSPs)
for liquid chromatography: the “a of the resolution equation 51 5
12.7 Packing process of high-efficiency chiral phases ( A/ in the resolution
equation) 534
12.8 Method development in chiral LC (adjustment of /c in the resolution
equation) 535
12.9 Special detectors in liquid chiral chromatography 536
12.10 Recent developments in enhancing chiral resolution using
ultrahigh efficiency supports 539
12.11 Instrumental considerations for fast chiral LC 544
12.12 Future directions and developments in chiral liquid chromatography 558
References 558
1 3. Enantioseparations by Capillary Electromigration Techniques 565
Bezhan Chankvetadze
13.1 Introduction 565
13.2 Separation principle in chiral CE: electrophoretic or chromatographic? 566
13.3 Enantioseparations with charged and uncharged chiral selectors 567
13.4 Enantioselective and nonselective phenomena in chiral CEKC 567
13.5 Similarities and differences between enantioseparations
by pressure-driven chromatography and CEKC 569
13.6 Modes of enantioseparations tn CEKC 574
13.7 Chiral selectors 584
13.8 Selector-selectand interaction in chiral CE 586
13.9 Mathematical models of CE enantioseparations 589
13.10 Enantioseparations in capillary electrochromatography 593
13.11 Future trends 600
References 601
14. Recent Developments in Chiral Separations by Supercritical
Fluid Chromatography 607
Roberta Franzini, Alessia Ciogli, Francesco Gasparrini, Omar H. Ismail,
Claudio Villani
14.1 Introduction 607
14.2 Chiral stationary phases for SFC 610
14.3 Analytical separations 612
14.4 Ultrafast high-efficient SFC separations 618
14.5 Conclusions 626
References 626
x Contents
15. Chiral Separation Strategies in Mass Spectrometry: Integration
of Chromatography, Electrophoresis, and Gas-Phase Mobility 631
James N. Dodds, Jody C. May, John A. McLean
15.1 Introduction 631
1 5.2 Chromatography and mass spectrometry 633
15.3 Liquid chromatography 635
1 5.4 Electrophoresis-mass spectrometry 637
15.5 Isomer separations by IM-MS 640
15.6 Conclusions 643
References 644
Part Four Emerging Methods 647
16. Cavity-based Chiral Polarimetry 649
Dimitris Sofikitis, George E. Katsoprinakis, Alexandros K. Spiliotis,
T. Peter Rakitzis
16.1 Introduction 649
16.2 Optical activity 650
16.3 Single-pass polarimetry 652
16.4 Cavity ring-down polarimetry 654
16.5 Cavity ring-down polarimetry with signal reversals 660
16.6 Continuous-wave cavity-enhanced polarimetry with signal reversals 672
16.7 Future outlook and conclusions 675
References 676
17. Quantitative Chiral Analysis by Molecular Rotational
Spectroscopy 679
Brooks H. Pate, Luca Evangelisti, Walther Caminati, Yunjie Xu,
Javix Thomas, David Patterson, Cristobal Perez, Melanie Schnell
17.1 Introduction 679
17.2 Basic principles of molecular rotational spectroscopy 682
17.3 Chiral tag rotational spectroscopy for enantiomer analysis 698
17.4 Three-wave mixing rotational spectroscopy for enantiomer analysis 714
17.5 Conclusions 723
References 725
18. Chiral Rotational Spectroscopy 731
Robert P. Cameron, Jörg B. Götte, Stephen M. Barnett
18.1 Introduction 731
18.2 Chiral rotational spectroscopy * 732
Contents xi
18.3 Chiral rotational spectra 734
18.4 Chiral rotational spectrometer 743
References 747
1 9. Chiral Analysis and Separation Using Molecular Rotation 753
Mirianas Chachisvilis
19.1 Introduction 753
19.2 Chiral separations in SFs 754
19.3 Chiral separations in REFs 762
19.4 Summary 776
References 776
index
779
Second Edition
Chiral Analysis
Advances in Spectroscopy, Chromatography and Emerging Methods
Edited by Prasad L. Polavarapu
Modern methods of chiral analysis, including emerging spectroscopic methods, and their application in drug
discovery and related areas
Broad coverage - this is the only volume to cover both spectroscopic and separation methods in a single
volume
• Up-to-date and detailed review of the various techniques available, including new techniques that have
emerged since the first edition
• Contributions from a range of leading experts in the field, now edited by award-winning chirality researcher
Prasad Polavarapu
Chiral Analysis serves as a resource for scientists interested in the general area of chirality and chiral analysis, in
particular. It covers an important area of analytical chemistry of relevance to a wide variety of scientific professionals,
including chemistry graduate students, analytical chemists, organic chemists, professionals in the pharmaceutical
industry, and others with an interest in chirality and chiral analysis. This thoroughly revised second edition
includes coverage of several new, important areas of chiral analysis that have emerged since the first edition.
Three of the new methods provide higher sensitivity than can be realized with the current methods and are expected
to become mainstream applications: cavity based methods offer vastly higher sensitivity than conventional
polarimetric methods, microwave chiral detection provides unsurpassed sensitivity for identifying diastereomers,
and rotating electric field method offers a competing new approach for the separation of enantiomers. Another
topic, chirality in extraterrestrial life, has not been discussed in any other book and is important for understanding
the origin of life.
This book is ideal for scientific professionals with an undergraduate background in chemistry or a related discipline,
specifically analytical chemists, medicinal and organic chemists; researchers in drug discovery, pharmaceutical
researchers involved with process analysis or combinatorial libraries; graduate students in chemistry as well as
regulatory food and drugs agencies, environmental agencies.
Prasad L. Polavarapu obtained his Master of Science degreein 1972 from Birla Institute ofTechnology and Science,
Pilani, and earned his Ph. D at the Indian Institute ofTechnology. Madras (now Chennai). He conducted research at
the University of Toledo, Toledo, OH, and Syracuse University, Syracuse, NY before joining Vanderbilt University,
Nashville, TN, as an Assistant Professor of Chemistry, where he later became a Professor. Professor Polavarapu has
made pioneering contributions in the research areas of specific optical rotation, vibrational Raman optical activity,
vibrational circular dichroism, and electronic circular dichroism (collectively referred to as Chiroptical Spectroscopy).
His research work led to determination of the absolute configurations of bromochlorofluoromethane and isoflurane
(a fluorinated ether used as an anesthetic) for the first time. He has published approximately 260 peer reviewed
research papers in leading scientific journals. Professor Polavarapu was awarded the Jeffrey Nordhaus Award (in
2010) for excellence in undergraduate teaching at Vanderbilt University. He was elected (in 2012) as a Fellow of the
American Association for Advancement of Science (AAAS) for distinguished contributions to the field of chiral
molecular structure determination. He was an Erudite Scholar (in November 2010) and Distinguished Consulting
Research Professor (in 2012) at Mahatma Gandhi University, Kottayam.
PHYSICAL SCIENCES.
elsevier.com/books-and-joumals
ANALYTICAL CHEMISTRY
ISBN 978-0-444-64027-7
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title | Chiral analysis advances in spectroscopy, chromatography and emerging methods |
title_auth | Chiral analysis advances in spectroscopy, chromatography and emerging methods |
title_exact_search | Chiral analysis advances in spectroscopy, chromatography and emerging methods |
title_full | Chiral analysis advances in spectroscopy, chromatography and emerging methods edited by Prasad L. Polavarapu, Vanderbilt University, Nashville, TN, United States |
title_fullStr | Chiral analysis advances in spectroscopy, chromatography and emerging methods edited by Prasad L. Polavarapu, Vanderbilt University, Nashville, TN, United States |
title_full_unstemmed | Chiral analysis advances in spectroscopy, chromatography and emerging methods edited by Prasad L. Polavarapu, Vanderbilt University, Nashville, TN, United States |
title_short | Chiral analysis |
title_sort | chiral analysis advances in spectroscopy chromatography and emerging methods |
title_sub | advances in spectroscopy, chromatography and emerging methods |
topic | Chemische Analyse (DE-588)4009840-0 gnd Chirale Verbindungen (DE-588)4348527-3 gnd Chiralität Chemie (DE-588)4147732-7 gnd Analytische Chemie (DE-588)4129906-1 gnd |
topic_facet | Chemische Analyse Chirale Verbindungen Chiralität Chemie Analytische Chemie |
url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030253824&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030253824&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
work_keys_str_mv | AT polavarapuprasadl chiralanalysisadvancesinspectroscopychromatographyandemergingmethods |