Imidazolium-based and related multidentate halogen-bond donors: synthesis, characterization and application in substitution and Diels-Alder reactions
Saved in:
| Main Author: | |
|---|---|
| Format: | Thesis Book |
| Language: | English |
| Published: |
München
Verl. Dr. Hut
2013
|
| Edition: | 1. Aufl. |
| Series: | Organische Chemie
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | 173 S. graph. Darst. |
| ISBN: | 9783843911849 |
Staff View
MARC
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| 245 | 1 | 0 | |a Imidazolium-based and related multidentate halogen-bond donors |b synthesis, characterization and application in substitution and Diels-Alder reactions |c Sebastian Michael Walter |
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| 264 | 1 | |a München |b Verl. Dr. Hut |c 2013 | |
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Record in the Search Index
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|---|---|
| adam_text | INDEX
1) INTRODUCTION 1
1.1) HALOGEN BONDS 2
1.1.1) DEFINITION AND HISTORY OF HALOGEN BONDS 2
1.1.2) THEORETICAL BACKGROUND 4
1.2) APPLICATIONS OF HALOGEN BONDS IN SOLUTION 12
1.2.1) HALOGEN BONDING IN ANION RECOGNITION 12
1.2.2) HALOGEN BONDING IN TEMPLATE-DRIVEN SELF-ASSEMBLY 14
1.2.3) HALOGEN BONDING IN MEDICINAL CHEMISTRY 1S
1.3) ORGANOCATALYSIS 15
1.3.1) HALOGEN BONDING IN ORGANOCATALYSIS 18
1.4) OBJECTIVES 19
1.5) REFERENCES 21
2) HALOGEN BONDING AND
K
-
K
INTERACTIONS IN THE SOLID-STATE STRUCTURE OF A BUTADIYNYLENE-
LINKED BIS(IODOPERFLUOROARENE) 29
SUMMARY 29
2.1) INTRODUCTION 30
2.2) RESULTS AND DISCUSSION 31
2.3) CONCLUSIONS 37
2.4) REFERENCES 38
2.5) SUPPORTING INFORMATION 40
3) HALOGEN-BOND-INDUCED ACTIVATION OF A CARBON-HETEROATOM BOND 41
SUMMARY 41
3.1) INTRODUCTION 42
3.2) RESULTS AND DISCUSSION 43
3.3) REFERENCES 49
3.4) SUPPORTING INFORMATION 52
HTTP://D-NB.INFO/1042080313
3.4.1) GENERAL PROCEDURE FOR THE NMR EXPERIMENTS 52
3.4.2) ANALYSIS OF THE SPECTRA (DETERMINATION OF THE YIELD OF 5) S3
3.4.3) KINETICS OF THE RITTER-LIKE REACTIONS (GRAPHICAL REPRESENTATIONS)
53
4) 4,4 -AZOBIS(HALOPYRIDINIUM) DERIVATIVES: STRONG MULTIDENTATE
HALOGEN-BOND DONORS
WITH A REDOX-ACTIVE CORE 57
SUMMARY 57
4.1) INTRODUCTION 58
4.2) RESULTS AND DISCUSSION 59
4.3) EXPERIMENTAL SECTION 66
4.4) REFERENCES 66
4.5) SUPPORTING INFORMATION 71
4.5.1) GENERAL PROCEDURE FOR THE NMR EXPERIMENTS 71
4.5.2) ANALYSIS OF THE SPECTRA (DETERMINATION OF THE YIELD OF 5) 71
4.5.3) BENZHYDRYL BROMIDE BENCHMARK REACTION EXPERIMENTS 72
4.5.4) KINETICS OF THE RITTER-LIKE REACTIONS (GRAPHIC REPRESENTATIONS)
73
4.5.5) X-RAY STRUCTURAL ANALYSES 74
5) 5-IODO-L,2,3-TRIAZOLIUM-BASED MULTIDENTATE HALOGEN-BOND DONORS AS
ACTIVATING
REAGENTS 77
SUMMARY 77
5.1) INTRODUCTION 78
5.2) RESULTS AND DISCUSSION 78
5.3) REFERENCES 84
5.4) SUPPORTING INFORMATION 86
5.4.1) GENERAL PROCEDURE FOR THE NMR EXPERIMENTS 86
5.4.2) ANALYSIS OF THE SPECTRA (DETERMINATION OF THE YIELD OF 5) 86
5.4.3) KINETICS OF THE RITTER-LIKE REACTIONS (GRAPHICAL REPRESENTATIONS)
87
5.4.4) KINETICS OF THE RITTER-LIKE REACTIONS (TABLE SI) 88
5.4.5) X-RAY STRUCTURAL ANALYSIS 89
6) POLYFLUORINATED
VERSUS
CATIONIC MULTIDENTATE HALOGEN-BOND DONORS: A DIRECT
COMPARISON 91
SUMMARY 91
6.1) INTRODUCTION 92
6.2) RESULTS AND DISCUSSION 93
6.2.1) SYNTHESIS OF NEUTRAL MULTIDENTATE HALOGEN-BOND DONORS 4A AND 4B
93
6.2.2) X-RAY STRUCTURAL ANALYSIS: COMPARISON OF THE ORIENTATIONS OF THE
IODINE
SUBSTITUENTS IN COMPOUNDS 4A AND 1 94
6.2.3) PERFORMANCE IN A BENCHMARK CARBON-HALOGEN BOND ACTIVATION
REACTION 96
6.2.4) QUANTUM-CHEMICAL CALCULATIONS 99
6.3) CONCLUSIONS 100
6.4) EXPERIMENTAL 101
6.4.1) GENERAL 101
6.4.2) HALIDE ABSTRACTION BENCHMARK REACTIONS 102
6.5) REFERENCES 105
6.6) SUPPORTING INFORMATION 110
7) ISOTHERMAL CALORIMETRIC TITRATIONS ON CHARGE-ASSISTED HALOGEN BONDS:
ROLE OF ENTROPY,
COUNTERIONS, SOLVENT, AND TEMPERATURE 111
SUMMARY ILL
7.1) INTRODUCTION 112
7.2) RESULTS AND DISCUSSION 114
7.2.1) DERIVATIZATION OF XB DONORS 114
7.2.2) ROLE OF ENTROPY AND FIRST ASSESSMENT OF BINDING 114
7.2.3) NATURE OF THE INTERACTION 118
7.2.4) TEMPERATURE DEPENDENCE AND STRUCTURAL VARIATIONS 119
7.2.5) SOLVENT EFFECTS 121
7.2.6) CONCLUSIONS 122
7.3) REFERENCES 122
7.4) SUPPORTING INFORMATION 127
7.4.1) SINGLE CRYSTAL X-RAY STRUCTURE DETERMINATION OF COMPOUND
M
-N
-L
ME
/BPH4L27
8) ORGANOCATALYSIS BY NEUTRAL HALOGEN-BOND DONORS 129
SUMMARY 129
8.1) INTRODUCTION 130
8.2) RESULTS AND DISCUSSION 131
8.3) REFERENCES 138
8.4) SUPPORTING INFORMATION 142
9) CATALYTIC ACTIVATION OF A CARBONYL GROUP BY HALOGEN BONDING 143
SUMMARY 143
9.1) INTRODUCTION 144
9.2) RESULTS AND DISCUSSION 145
9.3) REFERENCES 150
9.4) SUPPORTING INFORMATION 153
9.4.1)
DIELS-ATDER
MEASUREMENTS 154
9.4.2) SYNTHESES AND EXPERIMENTAL DATA 155
10) CONCLUSIONS AND OUTLOOK 167
APPENDIX 171
PUBLICATION LIST 171
CONTRIBUTIONS TO SCIENTIFIC CONFERENCES 172
CURRICULUM VITAE 173
|
| any_adam_object | 1 |
| author | Walter, Sebastian Michael |
| author_facet | Walter, Sebastian Michael |
| author_role | aut |
| author_sort | Walter, Sebastian Michael |
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| ctrlnum | (OCoLC)859422035 (DE-599)BVBBV041286976 |
| dewey-full | 547.2 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.2 |
| dewey-search | 547.2 |
| dewey-sort | 3547.2 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| edition | 1. Aufl. |
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| indexdate | 2024-07-10T00:53:25Z |
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| isbn | 9783843911849 |
| language | English |
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| physical | 173 S. graph. Darst. |
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| publisher | Verl. Dr. Hut |
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| series2 | Organische Chemie |
| spelling | Walter, Sebastian Michael Verfasser aut Imidazolium-based and related multidentate halogen-bond donors synthesis, characterization and application in substitution and Diels-Alder reactions Sebastian Michael Walter 1. Aufl. München Verl. Dr. Hut 2013 173 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Chemie Zugl.: München, Techn. Univ., Diss., 2013 Imidazoliumsalze (DE-588)4347498-6 gnd rswk-swf Substitutionsreaktion (DE-588)4183927-4 gnd rswk-swf Diels-Alder-Reaktion (DE-588)4149746-6 gnd rswk-swf Halogenorganische Verbindungen (DE-588)4357900-0 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Imidazoliumsalze (DE-588)4347498-6 s Halogenorganische Verbindungen (DE-588)4357900-0 s Substitutionsreaktion (DE-588)4183927-4 s Diels-Alder-Reaktion (DE-588)4149746-6 s DE-604 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026736038&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Walter, Sebastian Michael Imidazolium-based and related multidentate halogen-bond donors synthesis, characterization and application in substitution and Diels-Alder reactions Imidazoliumsalze (DE-588)4347498-6 gnd Substitutionsreaktion (DE-588)4183927-4 gnd Diels-Alder-Reaktion (DE-588)4149746-6 gnd Halogenorganische Verbindungen (DE-588)4357900-0 gnd |
| subject_GND | (DE-588)4347498-6 (DE-588)4183927-4 (DE-588)4149746-6 (DE-588)4357900-0 (DE-588)4113937-9 |
| title | Imidazolium-based and related multidentate halogen-bond donors synthesis, characterization and application in substitution and Diels-Alder reactions |
| title_auth | Imidazolium-based and related multidentate halogen-bond donors synthesis, characterization and application in substitution and Diels-Alder reactions |
| title_exact_search | Imidazolium-based and related multidentate halogen-bond donors synthesis, characterization and application in substitution and Diels-Alder reactions |
| title_full | Imidazolium-based and related multidentate halogen-bond donors synthesis, characterization and application in substitution and Diels-Alder reactions Sebastian Michael Walter |
| title_fullStr | Imidazolium-based and related multidentate halogen-bond donors synthesis, characterization and application in substitution and Diels-Alder reactions Sebastian Michael Walter |
| title_full_unstemmed | Imidazolium-based and related multidentate halogen-bond donors synthesis, characterization and application in substitution and Diels-Alder reactions Sebastian Michael Walter |
| title_short | Imidazolium-based and related multidentate halogen-bond donors |
| title_sort | imidazolium based and related multidentate halogen bond donors synthesis characterization and application in substitution and diels alder reactions |
| title_sub | synthesis, characterization and application in substitution and Diels-Alder reactions |
| topic | Imidazoliumsalze (DE-588)4347498-6 gnd Substitutionsreaktion (DE-588)4183927-4 gnd Diels-Alder-Reaktion (DE-588)4149746-6 gnd Halogenorganische Verbindungen (DE-588)4357900-0 gnd |
| topic_facet | Imidazoliumsalze Substitutionsreaktion Diels-Alder-Reaktion Halogenorganische Verbindungen Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026736038&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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