Carbohydrate-Metal Chemistry: Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography
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| 245 | 1 | 0 | |a Carbohydrate-Metal Chemistry |b Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography |c Thorsten Allscher |
| 264 | 1 | |c 2011 | |
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| _version_ | 1804148605614817280 |
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| adam_text | IMAGE 1
CONTENTS
1 INTRODUCTION 1
1.1 THE BIOLOGICAL IMPORTANCE OF CARBOHYDRATES 1
1.2 INDUSTRIAL APPLICATIONS OF CARBOHYDRATES 2
1.3 CARBOHYDRATE STRUCTURE AND CONFORMATION 8
1.4 NMR SPECTROSCOPY AND THE KARPLUS EQUATION 14
1.5 AIMS OF THIS WORK 17
2 RESULTS 19
2.1 PALLADIUM(II) FRAGMENTS: NOMENCLATURE AND CHARACTERISTICS 19
2.1.1 [PD(DMEN)(OH) 2] AND [PD(TMEN)(OH)2] 20
2.1.2 [PD(TMCHXN)(OH) 2] 21
2.1.3 [PD(TEEN)(OH) 2] 23
2.1.4 [PD(TN)(OH) 2] 24
2.1.5 [PDCBPYXOHK] AND [PD(PHEN)(OH) 2] 24
2.2 SIMPLE DIOLS: ETHANE-1,2-DIOL AND ANHYDROERYTHRITOL COMPLEXES WITH
PD-PHEN 26
2.3 THE POLYOLS: OPEN-CHAIN CARBOHYDRATE COMPLEXES OF PALLADIUM(II) 28
2.3.1 THE TETRITOLS: ERYTHRITOL AND D-THREITOL 30
2.3.2 THE PENTITOLS: RIBITOL AND XYLITOL 33
2.3.3 THE HEXITOLS 33
2.4 PALLADIUM(II)-POLYOL COMPLEXES IN NEUTRAL AQUEOUS SOLUTION 47
2.4.1 N-TRIOLATO-CHELATION AND LIGAND CONFORMATION AT PH 8-9 48
2.4.2 PD4(U-OH) 4-DERIVED /AREO-TETRAOLATO BRIDGING AT PH 7-8 54
2.4.3 PD 3(N-OH)3-DERIVED TRIOLATO BRIDGING AT PH 7-8 62
2.5 DIHYDROXYMALONIC ACID-COMPLEXES OF PALLADIUM(II) WITH KETONE
HYDRATES 65
2.6 THE INOSITOLS: FROM POLYOLS TO PYRANOSE RINGS 66
2.7 CONFORMATIONAL FLUCTUATION IN PALLADIUM(II}-METHYL
ALDOPENTOPYRANOSIDE COMPLEXES 74
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1016713142
DIGITALISIERT DURCH
IMAGE 2
2.8 METALATION-INDUCED CONFORMATIONAL FLUCTUATION OF
PALLADIUM(II)-ALDOPENTOSE COMPLEXES 84
2.8.1 D-ARABINOSE 85
2.8.2 D-RIBOSE 91
2.8.3 D-LYXOSE 95
2.8.4 D-XYLOSE 101
2.9 COORDINATION-INDUCED SHIFT PATTERNS OF PALLADIUM(U)-METHYL
HEX(UL)OSIDE COMPLEXES 105
2.9.1 THE METHYL HEXOPYRANOSIDES OF D-GALACTOSE, D-GLUCOSE AND D-MANNOSE
105
2.9.2 THE METHYL FRUCTOSIDES 113
2.10 PALLADIUM(N) CHELATION WITH PD-TMEN BY THE COMMON HEXOSES 118
2.10.1 D-GALACTOSE 119
2.10.2 D-GLUCOSE 121
2.10.3 D-MANNOSE 123
2.11 THE DIFFICULT DETERMINATION OF THE PALLADIUM(II)-HEXULOSE COMPLEXES
126
2.11.1 D-FRUCTOSE 127
2.11.2 D-TAGATOSE 130
2.11.3 L-SORBOSE 133
2.11.4 D-PSICOSE 135
2.12 THE DIALDOSES: A FIRST INVESTIGATION 137
2.12.1 ERYFARO-TETRODIALDOSE 138
2.12.2 JRY/O-PENTODIALDOSE 139
2.12.3 GA/ACTO-HEXODIALDOSE 142
2.12.4 D-MANNO-HEXODIALDOSE 145
2.13 THE FRUCTOSE-CONTAINING DI- AND TRISACCHARIDES 149
2.13.1 D-SUCROSE 150
2.13.2 D-TURANOSE 152
2.13.3 D-MALTULOSE 153
2.13.4 D-LACTULOSE 154
2.13.5 D-LEUCROSE 155
2.13.6 D-PALATINOSE 157
2.13.7 D-MELECITOSE 158
II
IMAGE 3
2.13.8 D-RAFFINOSE 159
2.14 FROM DISACCHARIDES TO THE POLYSACCHARIDES WITH SS-CONNECTED UNITS
161
2.14.1 D-LACTOSE 161
2.14.2 D-CELLOBIOSE AND CELLULOSE 163
2.15 FROM DISACCHARIDES TO THE OLIGOSACCHARIDES WITH A-CONNECTED UNITS
166
2.15.1 A,A-D-TREHALOSE 168
2.15.2 D-MELIBIOSE 169
2.15.3 D-MALTOSE 171
2.15.4 D-MALTOTRIOSE 173
2.15.5 D-MALTOHEPTAOSE AND AMYLOSE 178
2.16 THE CYCLODEXTRINS 181
3 DISCUSSION 185
3.1 THE PD NN 2 FRAGMENTS: CHARACTERISTICS AND DIFFERENCES 185
3.2 THEPD N 2 FRAGMENTS INFLUENCE ON THE HYDROGEN-BONDING NETWORK 186
3.3 CONFORMATIONAL FLUCTUATION IN PALLADIUM(II)-METHYL
ALDOPENTOPYRANOSIDE AND ALDOPENTOSE
COMPLEXES 188
3.4 METALATION OF THE METHYL HEX(UL)OSIDES 190
3.5 METALATION OF THE HEXOSES 190
3.6 THE HEXULOSES CHELATION PREFERENCES 193
3.7. THE DIFFICULT ANALYSIS OF THE DIALDOSES 196
3.8 METALATION OF DI- AND OLIGOSACCHARIDES 197
4 SUMMARY 201
5 EXPERIMENTAL SECTION 207
5.1 METHODS AND MATERIALS 207
5.2 REAGENTS AND SOLVENTS 207
5.3 NMR SPECTROSCOPY 210
5.4 CRYSTAL STRUCTURE DETERMINATION AND REFINEMENT 211
5.4 PREPARATION OF PALLADIUM(II) COMPOUNDS 212
5.4.1 [PD(EN)CL 2] 212
5.4.2 [PD(EN)(OH)2] (0.45 M) 212
III
IMAGE 4
5.4.3 [PD(AE,AE-CHXN)CL 2] 213
5.4.4 [PD(AE,AE-CHXN)(OH) 2] (0.45 M) 213
5.4.5 ACAWW-TETRAMEMYL-OAE^-CYCLOHEXANE-L^-DIAMINE (TMCHXN) 213
5.4.6 [PD(TMCHXN)CL 2] 214
5.4.7 [PD(TMCHXN)(OH) 2] (0.45 M) 214
5.4.8 [PD(DMEN)CL 2] 215
5.4.9 [PD(DMEN)(OH) 2] (0.45 M) 215
5.4.10 [PD(TMEN)CL 2] 215
5.4.11 [PD(TMEN)(OH) 2] (0.45 M) 215
5.4.12 [PD(TEEN)CL 2] 216
5.4.13 [PD(TEEN)(OH) 2] (0.45 M) 216
5.4.14 [PD(TN)CL 2] 216
5.4.15 [PD(TNXOH) 2] (0.45 M) 217
5.4.16 [PD(BPY)CL 2] 217
5.4.17 [PD(BPY)(OH) 2] (0.45 M) 217
5.4.18 [PD(PHEN)CL 2] 217
5.4.19 [PDTPHENXOHM (0.45 M) 218
5.5 PREPARATION OF CARBOHYDRATES 218
5.5.1 METHYL A-D-LYXOPYRANOSIDE 218
5.5.2 METHYL D-FRUCTOSIDES 218
5.5.3 *Y/O-PENTODIALDOSE 219
5.5.4 GA/AC/O-HEXODIALDOSE 219
5.5.5 D-MO/MO-HEXODIALDOSE 220
5.6 PREPARATION OF THE CRYSTALLINE COMPOUNDS 221
5.6.1
DIHYDROXIDO-AF,JV,7V ,IV -TETRAMETHYLETHANE-L^-DIAMINE-PALLADIUM(N)
DIHYDRATE 221
5.6.2 I7
2-CARBONATO-IV;IV;IVYV-TETRAME%L-(LAE^)- ^CLOHEXANE-L^-DAMINE-PALLADIURN(N)
HEXAHYDRATE 221
5.6.3 YV,IV,JV,AR -TETRAETHYLETHANE-L^-DIAMMONIUM
TETRACHLORIDOPALLADATE(II) 221
5.6.4 DICHORIDO-AUV;AR,7/ -TETRAETHYLETHANE-L^-DIAMINE-PALLADIUM(N)
DIHYDRATE 221
5.6.5 2^ -BIPYRIDINE-DIHYDROXIDO-PALLADIUM(II) PENTAHYDRATE 222
IV
IMAGE 5
5.6.6 DIHYDROXIDO-L,10-PHENANTHROLME-PALLADIUM(N) PENTAHYDRATE 222
5.6.7 ETHANEDIOLATO-KO - 2-L,10-PHENANTHROLINE-PALLADIUM(H) HEPTAHYDRATE
222
5.6.8 ANHYDROERYTHRITOLATO-KO 2F3-L,10-PHENANTHROLINE-PALLADIUM(II)
4.5-HYDRATE 222
5.6.9 BIS(AYV -DIMETHYLETHANE-L^-DIAMINE)(ERYTHRITOIATO-KO
;2:KO3 4)D PALLADIUM(N)
14-HYDRATE 222
5.6.10 DIPROPANE-L,3-DIAMINE(ERYTHRITOLATO-KO U:KO3 T)DIPALLADIUM(H)
10-HYDRATE 223
5.6.11 BIS(AT,AR,IV^-TETRAMETHYLEMANE-L,2-DIAMINE)(MANNITOLATO-K0
1-2:K03I4)DIPALLADIURN(II)
9-HYDRATE 223
5.6.12 DIPROPANE-L,3-DIAMME(MANNITOLATO-ICO 2:ICO3 4)DIPALLADIURN(FL)
5-HYDRATE 223
5.6.13 BIS(IV RIV -DIMETHYLETHANE-L,2-DIAMINE)(DULCITOIATO-K0
2J:K04 5)DIPALLADIUM(II)
8-HYDRATE 223
5.6.14 DIPROPANE-L,3-DIAMINE(DULCITOLATO-KO 2-3:KO4|3)DIPALLADIUM(II)
6-HYDRATE 224
9-HYDRATE 224
5.6.16 DIETHANE-L,2-DIAMINE(ALLITOLATO-KO 2; :KO4-5)DIPALLADIUM(II)
14-HYDRATE 224
5.6.17 BIS(AT,^IV ,IV -TETRAMETHYLETHANE-L,2-DIAMINEXALLITOLATO-KO
1-2:KO56)DIPALIADI NI(II)
8-HYDRATE 224
5.6.18 [(PD N 2),,(U2-OH),,R*-DERIVED BRIDGED COMPOUNDS AT PH 7-8 225
5.6.19 [PD4(AE,AE-CHXN) 4(C3O6)(U-OH)](NO3)3 * 8 H20 225
5.6.20 DIETHANE-L^-DIAMINE(D-CAITO-INOSITOLATO-KO
U.ICO5-6)DIPALLADIUM(H) 8-HYDRATE 225
5.6.21 BISWA^JV^AR^TETRAMETHYLETHANE-L^-DIAMINEXNEO-INOSITOLATO-ICO ^KO
4)- DIPALLADIUM(II) 22-HYDRATE 225
5.6.22 TRIS(AR,AT,IV ,AR -TETRAMETHYLETHANE-L
2-DIAMINEXICY//O-MOSITOLATO-KO U:K03-4:K03 )- TRIPALLADIUM(II)
23-HYDRATE 226
5.6.23
(LAE,2AE)-CYCLOHEXANE-L^-DIAMINE(METHYLA-D-LYXOPYRANOS-2,3-0-DIATO-K0
2 3)- PALLADIUM(II) 2.25-HYDRATE 226
5.6.24 IV,IV,IV ,W-TETRAMETHYLETHANE-L^-DIAMINE(METHYL
SS-D-XYLOPYRANOS-2,3-O-DIATO- KO
2J)PALLADIUM(H)-^,JV,AT,IV-TETRAMETHYLETHANE-L ^-DIAMINE(METHYL
SS-D-XYLOPYRANOS-3,4-O- DIATO-KO 3I4)PALLADIUM(II) DIHYDRATE 226
5.6.25 BIS(JV,IV, WV-TETRAMETHYLETHANE-1 ^-DIAMINE)(SS-D-ARABINOPYRANOS-L
^;3,4-O-DIATO- KO U:KO3-4)DIPALLADIUM(II) 10-HYDRATE 226
V
IMAGE 6
5.6.26
BIS(AF,AR,IV ,IV-TETRAMETHYLETHANE-L,2-DIAMINEXSS-D-LYXOPYRANOS-L,2;3,4-O-DIATO-
KO I 2:ICOI 4)DIPALLADIUM(N) 10-HYDRATE 227
5.6.27
A^IVIJV .AF-TETRAMETHYLETHANE-L^-DIAMINEFMETHYLA-D-GALACTOPYRANOS-S^-O-DIATO-
KO -^PALLADIUM^ 8-HYDRATE 227
5.6.28 A^JV -DIMETHYLETHANE-L ,2-DIAMINE(METHYL
A-D-GALACTOPYRANOS-S^-O-DIATO-ICO 3 4)
PALLADIUM(II) 9-HYDRATE 227
5.6.29 AYV,JV IV-TETRARNETHYLETHANE-L,2-DIAMINE(METHYL
A-D-MANNOPYRANOS-2,3-O-DIATO- K ^ ^ A L L A D I U M^ 3.5-HYDRATE 227
5.6.30 (LAE^AE^YCLOHEXANE-L^-DIAMINE^ETHYLA-D-FRUCTOFURANOS-L.S-O-DIATO-KO
1 3)
PALLADIUM(II) 2-HYDRATE 228
5.6.31
BIS(IV,AF,AF,AR -TETRAMETHYLETHANE-L,2-DIAMINEXA-D-TAGATOPYRANOS-L^;3
4-O-DIATO- KO - 2:KO3 4)DIPALIADIUM(II) 8-HYDRATE 228
5.6.32
BIS(IV,ACW ,^TETIMNETHYLEMANE-L,2-DIARNME)(E77RTTO-TETRODIALDOFURANOSL,4;2,3-
O-DIATO-KO - 4:KO2J)DIPALLADIUM(II) 8-HYDRATE 228
5.6.33 [PD 3(TEEN)3(A-CDH-S)] * 34 H2O 228
5.6.34 [PD 3(TMEN)3(A-CDH )] * 20.7 H2O * ACETONE 229
5.6.35 [PD4(TEEN) 4(Y-CDH-8)] * 12 H 20 229
5.6.36 [PD4(TMEN) 4(Y-CDH-8)] * 65.79 H2O * 0.96 [PD(TMEN)CO3] 229
5.7 H NMR CHEMICAL SHIFTS OF THE METHYL PENTOSIDES AND HEX(UL)OSIDES,
THE PENTOSES,
THE HEX(UL)OSES AND THE DIALDOSES 230
5.8 COMPUTATIONAL METHODS AND RESULTS 239
6 APPENDIX 241
6.1 13C NMR SPECTRA AND CHEMICAL SHIFTS OF UNCOORDINATED CARBOHYDRATES
241
6.2 PACKING DIAGRAMS OF THE CRYSTAL STRUCTURES 282
6.3 CRYSTALLOGRAPHIC TABLES 327
BIBLIOGRAPHY 343
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| spelling | Allscher, Thorsten 1981- Verfasser (DE-588)1015525881 aut Carbohydrate-Metal Chemistry Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography Thorsten Allscher 2011 Online-Ressource txt rdacontent n rdamedia nc rdacarrier München, Univ., Diss., 2011 (DE-588)4113937-9 Hochschulschrift gnd-content Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:19-134600 https://nbn-resolving.org/urn:nbn:de:bvb:19-134600 Resolving-System kostenfrei Volltext http://edoc.ub.uni-muenchen.de/13460/ Verlag kostenfrei DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=024573251&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Allscher, Thorsten 1981- Carbohydrate-Metal Chemistry Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography |
| subject_GND | (DE-588)4113937-9 |
| title | Carbohydrate-Metal Chemistry Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography |
| title_auth | Carbohydrate-Metal Chemistry Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography |
| title_exact_search | Carbohydrate-Metal Chemistry Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography |
| title_full | Carbohydrate-Metal Chemistry Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography Thorsten Allscher |
| title_fullStr | Carbohydrate-Metal Chemistry Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography Thorsten Allscher |
| title_full_unstemmed | Carbohydrate-Metal Chemistry Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography Thorsten Allscher |
| title_short | Carbohydrate-Metal Chemistry |
| title_sort | carbohydrate metal chemistry complexes of palladium ii and their characterization via nmr spectroscopy and x ray crystallography |
| title_sub | Complexes of Palladium(II) and their Characterization via NMR Spectroscopy and X-Ray Crystallography |
| topic_facet | Hochschulschrift |
| url | https://nbn-resolving.org/urn:nbn:de:bvb:19-134600 http://edoc.ub.uni-muenchen.de/13460/ http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=024573251&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT allscherthorsten carbohydratemetalchemistrycomplexesofpalladiumiiandtheircharacterizationvianmrspectroscopyandxraycrystallography |