Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins:
Gespeichert in:
| 1. Verfasser: | |
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| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
1995
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Bonn, Univ., Diss., 1995 |
| Beschreibung: | III, 141 S. graph. Darst. |
Internformat
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Datensatz im Suchindex
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| adam_text | - 33O L CHIRAL DISCRIMINATION OF RACEMIC PHENETHYIAMINES USING NATIVE
AND ACETYLATED CYCLODEXTRINS INAUGURAL-DISSERTATION ZUR ERLANGUNG DES
DOKTORGRADES DER MATHEMATISCH-NATURWISSENSCHAFTLICHEN FAKULTAT DER
RHEINISCHEN FRIEDRICH-WILHELMS-UNIVERSITAT ZU BONN VORGELEGTVON HENNING
MALLWITZ BONN 1995 CONTENTS 1. INTRODUCTION 1 1.1. CHIRALITY AND ITS
IMPORTANCE 1 1.2. CHIRAL SEPARATIONS 2 1.2.1. ANALYTICAL METHODS OF
SEPARATION 2 1.2.2. SELECTORS FOR ENANTIOMERIC RESOLUTION 3 1.3.
CYDODEXTRINS 4 1.3.1. GENERAL PROPERTIES 4 1.3.2. CHIRAL DISCRIMINATION
6 1.4. AIM OF THIS STUDY AND SELECTION OF METHODS 7 2. SYNTHESIS 10
HEPTAKIS(2-DI-0-ACETYL)$-CYC ODEXTRIN 3 13
HEPTAKIS(6-0-ACTTYL)$-CYCLODEXTRIN 7 16
/FE/ RA/S(2-0-ACETYL)P-CYCLODEXTRIN 12 18
//^OA(3-0-ACETYL)(3-CYCLODEXTRIN 15 21 3. CAPILLARY ELECTROPHORESIS 23
3.1. BASIC THEORY OF CAPILLARY ELECTROPHORESIS 23 3.2. OPTIMISATION OF
CE CONDITIONS 29 3.2.1. INFLUENCE OF THE CONCENTRATION OF THE
CYDODEXTRINS 30 3.2.2. INFLUENCE OF THE BUFFER PH 32 3.2.3. INFLUENCE OF
ORGANIC MODIFIERS 33 3.2.3.1. ADDITION OF METHANOL 34 3.2.3.2. ADDITION
OF ACETONITRILE 35 3.2.3.3. ADDITION OF TETRAHYDROFURAN 37 3.2.4.
INFLUENCE OF THE BUFFER STRENGTH 38 3.2.5. CONTRIBUTIONS OF FUNCTIONAL
GROUPS TO ENANTIOMERIC RESOLUTION USING OPTIMISED CE CONDITIONS 40
3.2.5.1. PHENYLPROPYLAMINES 40 3.2.5.2. PHENYLETHYLAMINES 41 3.3.
MIGRATION TIMES OF SINGLE ENANTIOMERS 42 3.4. CONCLUSIONS 43 4. NMR
SPECTROSCOPY 44 4.1. DETERMINATION OF THE STOICHIOMETRY OF THE COMPLEX
47 4.2. L H NMR EXPERIMENTS WITH COMPLEXES OF RATIO 1:1 48 4.2.1. CHANGE
OF CHEMICAL SHIFTS AND SPLITTING OF THE PHENETHYLAMINE SIGNALS 48
CONTENTS 4.2.1.1. COMPLEXES WITH |3-CD 53 4.2.1.2. COMPLEXES WITH 6AC-CD
54 4.2.1.3. COMPLEXES WITH DIAC-CD 56 4.2.2. CHANGE OF THE CHEMICAL
SHIFTS OF THE CYCLODEXTRIN SIGNALS 57 4.2.3. CHANGE OF COUPLING
CONSTANTS OF THE CYDODEXTRINS 61 4.2.3.1. COUPLING CONSTANTS OF
3-CYCLODEXTRIN 61 4.2.3.2. COUPLING CONSTANTS OF 6AC-CD 61 4.2.3.3.
COUPLING CONSTANTS OF DIAC-CD 62 4.2.4. SPECTRA OF SINGLE ENANTIOMERS 63
4.2.4.1. CHANGES OF THE CHEMICAL SHIFTS 63 4.2.4.2. CHANGES OF THE
COUPLING CONSTANTS 65 4.3. NOE DIFFERENCE EXPERIMENTS 66 4.4.2D ROTATING
FRAME NOE EXPERIMENTS 69 4.4.1. ROESY SPECTRA OF THE COMPLEXES BETWEEN
RACEMIC OXILOFRINE AND P- CYDODEXTRIN AND 2,3-DIACETYL-CD 69 4.4.2.
ROESY SPECTRA OF THE COMPLEXES BETWEEN RACEMIC ETILEFRINE AND 3-
CYDODEXTRIN AND 2,3-DIACETYL CD 71 4.4.3. ROESY SPECTRA OF THE COMPLEXES
WITH SINGLE ENANTIOMERS OF EPHEDRINE 73 4.4.3.1 INTRAMOLECULAR NOES IN
EPHEDRINE 74 4.4.3.2. COMPLEXES BETWEEN SINGLE EPHEDRINE ENANTIOMERS AND
3-CD 74 4.4.3.3. COMPLEXES BETWEEN SINGLE EPHEDRINE ENANTIOMERS AND
6AC-CD 76 4.4.3.4. COMPLEXES BETWEEN SINGLE EPHEDRINE ENANTIOMERS AND
DIAC-CD 78 4.4.4. ROESY SPECTRA OF THE COMPLEXES WITH SINGLE ENANTIOMERS
OF METHYLEPHEDRINE 80 4.4.4.1. INTRAMOLECULAR NOES IN METHYLEPHEDRINE 80
4.4.4.2. COMPLEXES BETWEEN SINGLE METHYLEPHEDRINE ENANTIOMERS AND (3-CD
80 4.4.4.2. COMPLEXES BETWEEN SINGLE METHYLEPHEDRINE ENANTIOMERS AND
6AC-CD 82 4.4.4.3. COMPLEXES BETWEEN SINGLE METHYLEPHEDRINE ENANTIOMERS
AND DIAC-CD 84 5. UV SPECTROSCOPY 89 5.1. DETERMINATION OF THE
STOICHIOMETRY OF THE PHENETHYLAMINE COMPLEXES 90 5.2. MEASUREMENTS OF
THE CONSTANTS OF FORMATION 92 6. MOLECULAR MODELLING OF CYCLODEXTREVS 96
6.1 INTRAMOLECULAR DISTANCES IN CYDODEXTRINS 99 6.2 STRUCTURES OF THE
GEOMETRY OPTIMISED MOLECULES 102 7. DISCUSSION 106 8. SUMMARY 109 9.
EXPERIMENTAL 112 9.1. METHODS AND MATERIALS 112 CONTENTS HI 9.2.
SYNTHESIS OF THE COMPOUDS 1-9: 11 5 9.2.1. SYNTHESIS OF
/FEPTA&5(6-O-DIMETHYLSILYL-1,1,2-TRIMETHYLPROPYL)- P-CYCLODEXTRIN (1)
115 9.2.2. SYNTHESIS OF/F^PTOFE^^-DI-O-ACETYL-E-O-CDIMETHYLSILYL-L, 1,2-
TRIMETHYLPROPYL))P-CYCLODEXTRIN (2) 115 9.2.3. SYNTHESIS OF
#EPTAJFC(2,3-DI-O-ACETYL)3-CYCLODEXTRIN (3) 116 9.2.4. SYNTHESIS
OF/FE/?TA&X2,3-DI-O-BEIIZYL-6-O-(DIMETHYLSILYL-L, 1,2-
TRIMETHYLPROPYL))J3-CYCLODEXTRIN (4) 116 9.2.5. SYNTHESIS OF
#E/RTA/FCW(2,3-DI-O-BENZYL)P-CYCLODEXTRIN (5) 117 9.2.6. SYNTHESIS
OF//EPTOA75(2,3-DI-O-BENZYL-6-O-ACETYL)3-CYCLODEXTRIN (6) 117 9.2.7.
SYNTHESIS OF /FE/?TAFOSF6-0-ACETYL)P-CYCLODEXTRIN (7) 118 9.2.8.
SYNTHESIS OF /FE/?TAFOX 2 -O-BENZYL-6-O-DIMETHYLSILYL-L,
1,2-TRIMETHYLPROPYL)- 3-CYCLODEXTRIN (8) 118 9.2.9. SYNTHESIS OF
HEPTAKIS(2-OA)ETAYL-3-O-ACETYL-6-O-DIMETHYMYL-L, 1,2-
TRIMETHYLPROPYL)3-CYCLODEXTRIN (9) 119 9.3. 13 C NMR AND FAB-MS SPECTRA
OF I/E/RFA*IS(6-0-ACETYL)P-CYCLODEXTRIN 123 9.4. MIGRATION TIMES AND
RESOLUTION IN CAPILLARY ELECTROPHORESIS 124 9.5. CHEMICAL SHIFT DATA OF
THE CYDODEXTRINS 130 9.6. UV-ABSORPTION DATA OF THE PHENETHYIAMINES 132
9.7. INTRAMOLECULAR DISTANCES OF THE CYDODEXTRINS 133 10. REFERENCES 135
|
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| indexdate | 2024-07-09T17:55:50Z |
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| language | English |
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| spelling | Mallwitz, Henning Verfasser aut Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins vorgelegt von Henning Mallwitz 1995 III, 141 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Bonn, Univ., Diss., 1995 Enantiomerentrennung (DE-588)4135272-5 gnd rswk-swf Acetylgruppe (DE-588)4355837-9 gnd rswk-swf Cyclodextrine (DE-588)4148527-0 gnd rswk-swf Phenylethylamine (DE-588)4174237-0 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Phenylethylamine (DE-588)4174237-0 s Enantiomerentrennung (DE-588)4135272-5 s Cyclodextrine (DE-588)4148527-0 s Acetylgruppe (DE-588)4355837-9 s DE-604 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007073879&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Mallwitz, Henning Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins Enantiomerentrennung (DE-588)4135272-5 gnd Acetylgruppe (DE-588)4355837-9 gnd Cyclodextrine (DE-588)4148527-0 gnd Phenylethylamine (DE-588)4174237-0 gnd |
| subject_GND | (DE-588)4135272-5 (DE-588)4355837-9 (DE-588)4148527-0 (DE-588)4174237-0 (DE-588)4113937-9 |
| title | Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins |
| title_auth | Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins |
| title_exact_search | Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins |
| title_full | Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins vorgelegt von Henning Mallwitz |
| title_fullStr | Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins vorgelegt von Henning Mallwitz |
| title_full_unstemmed | Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins vorgelegt von Henning Mallwitz |
| title_short | Chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins |
| title_sort | chiral discrimination of racemic phenethylamines using native and acetylated cyclodextrins |
| topic | Enantiomerentrennung (DE-588)4135272-5 gnd Acetylgruppe (DE-588)4355837-9 gnd Cyclodextrine (DE-588)4148527-0 gnd Phenylethylamine (DE-588)4174237-0 gnd |
| topic_facet | Enantiomerentrennung Acetylgruppe Cyclodextrine Phenylethylamine Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007073879&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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