Tautomerism: concepts and applications in science and technology
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| Format: | Buch |
| Sprache: | English |
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Weinheim, Germany
Wiley-VCH Verlag GmbH & Co. KGaA
[2016]
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XX, 377 Seiten Illustrationen, Diagramme |
| ISBN: | 9783527339952 3527339957 |
Internformat
MARC
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| 245 | 1 | 0 | |a Tautomerism |b concepts and applications in science and technology |c edited by Liudmil Antonov |
| 264 | 1 | |a Weinheim, Germany |b Wiley-VCH Verlag GmbH & Co. KGaA |c [2016] | |
| 264 | 4 | |c © 2016 | |
| 300 | |a XX, 377 Seiten |b Illustrationen, Diagramme | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Tautomerie |0 (DE-588)4078171-9 |2 gnd |9 rswk-swf |
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Festkörperchemie | ||
| 653 | |a Physical Chemistry | ||
| 653 | |a Physical Organic Chemistry | ||
| 653 | |a Physikalische Chemie | ||
| 653 | |a Physikalische Organische Chemie | ||
| 653 | |a Solid State Chemistry | ||
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| 999 | |a oai:aleph.bib-bvb.de:BVB01-028950162 | ||
Datensatz im Suchindex
| _version_ | 1804176188464168961 |
|---|---|
| adam_text | *
1.1
1
.
1.1
1
.
1.2
1.1.3
1.2
1
.
2.1
1
.
2.2
1.2.3
1.3
2
2.1
2.2
2.3
94
2.5
2.6
2.7
2.8
2.9
1**|
CONTENTS
UST OF CONTRIBUTORS X V
PREFACE XIX
TAUTOMERISM: A HISTORICAL PERSPECTIVE 1
JOSEELGUERO
H EM O D Y N AM IC ASPECTS 2
WHAT IS WELL KNOWN 2
WHAT NEEDS TO BE COMPLETED 3
WHAT IS 111 KNOWN 4
KINETIC ASPECTS 5
WHAT IS
*
11 KNOWN 5
WHAT NEEDS TO BE COMPLETED 6
WHAT IS 111 KNOWN 6
CONCLUSIONS 6
REFERENCES 7
*TRIAGE* FOR TAUTOMERS: THE CHOICE BETWEEN EXPERIMENT AND
COMPUTATION 11
PETER J.TAYLORANDLIUDMIL ANTONOV
INTRODUCTION (ORIGINAL TEXT WRITTEN ^ 11
C/5
**
AMIDES 12
TAUTOMERISM IN ALICYCLIC LACTAMS SIX-MEMBERED RINGS 13
TAUTOMERISM IN ALICYCLIC LACTAMS: 2*PYRROLIDINONE 14
TAUTOMERISM IN OTHER FIVE-MEMBERED RING LACTAMS 16
TAUTOMERIC RATIOS REQUIRING COMPUTATION: ALICYCLIC
SS*DIKETONES 17
TAUTOMERIC RATIOS REQUIRING COMPUTATION: *MALEIC HYDRAZIDE18 *
TAUTOMER RATIOS REQUIRING COMPUTATION: 2-OXO DERIVATIVES OF
PYRROLE, FURAN, AND * AZOLE 20
TAUTOMERIC RATIOS REQUIRING COMPUTATION: COMPOUNDS CONTAINING
CONTIGUOUS CARBONYL GROUPS 22
TAUTOMERIC RATIOS REQUIRING COMPUTATION: COMPOUNDS CONTAINING
CONTIGUOUS *-DONORS 24
2.10
2.11 COMPOUNDS EQUALLY SUITED TO EXPERIMENT OR COMPUTATION:
*AZAPENTALENES* 25
2.12 PHENOMENA SUSCEPTIBLE TO EXPERIMENT OR COMPUTATION: LONE PAIR
EFFECTS 29
2.13 CONFORMATIONAL EFFECTS ON AMINOENONE STABILITY: A COMPUTATIONAL
APPROACH 30
2.14 OVERVIEW (ORIGINAL TEXT W RTO 32
REFERENCES 32
3 METHODS TO DISTINGUISH TAUTOMER
*
*
CASES FROM STATIC ONES 35
POUL ERIK HANSEN
3.1 INTRODUCTION 35
3.2 THE LIQUID STATE 36
3.2.1 N M R 3 *
3.2.1.1 IHNM R 36
3.2.1.2 15NNMR 38
3.2.1.3
13C
CHEMICAL SHIFTS 39
19.14
!9FNMR 41
3.2.1.5 17ONMR 41
3.2.2 ISOTOPE EFFECTS ON CHEMICAL SHIFTS 42
3.2.2.1 DEUTERIUM ISOTOPE EFFECTS ON 13C CHEMICAL SHIFTS 44
3.2.2.2 DEUTERIUM ISOTOPE EFFECTS ON 15N CHEMICAL SHIFTS 47
3.2.2.3 DEUTERIUM ISOTOPE EFFECTS ON 7
*
*
CHEMICAL SHIFTS 47
3.2.2.4 ISOTOPIC PERTURBATION OF EQUILIBRIUM 47
3.2.2.5 PRIMARY ISOTOPE EFFECTS 48
3.2.3 COUPLING CONSTANTS SI
3.2.3.1 !J(N
*
H) 51
3.2.3.2 ***) 52
3.2.4 MULTIPLE EQUILIBRIA 52
3.3 *V/VIS SPECTROSCOPY
53
3.4 INFRA RED SPECTROSCOPY 55
3.4.1 AMBIENT TEMPERATURE SPECTRA 55
3.4.2 MATRIX ISOLATION SPECTRA 56
3.5 TAUTOMERISM IN THE EXCITED STATE 56
3.6 NEAR-EDGE X-RAY 56
3.7 ENERGY-DISPERSIVE X-RAY 57
3.8 SOLID STATE 57
3.8.1 NMR 57
3.8.1.1 ISOTOPE EFFECTS ON CHEMICAL SHIFTS 58
3.8.2 X-RAY 59
3.9 SINGLE MOLECULE TAUTOMERIZATION 59
3.10 GAS PHASE
60
3.11 ^EO RETICAL CALCULATIONS 61
3.11.1 ENERGIES 62
3.11.2 NMR CHEMICAL SHIFTS 62
3.11.3
3.11.4
3.11.5
4
4.1
4 9
4.3
4.3.1
4.3.2
4.3.3
4.3.4
4.3.5
4.3.6
4.4
5
5.1
5.2
5.3
5.4
5.5
5.6
5.7
5.8
6
6.1
6.2
6
.
2.1
6
.
2.2
6.2.3
6.3
COUPLING CONSTANTS 66
ISOTOPE EFFECTS ON CHEMICAL SHIFTS 68
VIBRATIONAL SPECTRA 70
REFERENCES 71
ELECTRON-TRANSFER-INDUCED TAUTOMERIZATIONS 75
THOMAS BALLY
INTRODUCTION 75
METHODOLOGY 76
0 -ALKYL PHENYL KETONES 77
O-METHYLBENZOPHENONE 78
O-ALKYLACETOPHENONE DERIVATIVES 80
O-METHYLACETOPHENONE 81
7*METHYL* AND 4,7*DI*NETH*L*L *INDANONE 83
NADH ANALOGS 88
OTHER CASES OF TAUTOMERIZATIONS IN RADICAL CATIONS 91
CONCLUSIONS 93
ACKNOWLEDGMENTS 93
REFERENCES 94
THE FAULT LINE IN PROTOTROPIC TAUTOMERISM 95
PETERJ.TAYLORANDLIUDMIL ANTONOV
INTRODUCTION: * -T YPE* AND *C*TYPE* TAUTOMERISM 95
TAUTOMERISM IN SYMMETRICAL AMIDINES 96
TAUTOMER RATIO IN ASYMMETRIC HETEROAROMATIC AMIDINES 100
TAUTOMER RATIO IN THE IMINE-ENAMINE SYSTEM: SUBSTITUTION AT
NITROGEN 102
TAUTOMER RATIO IN THE IMINE-ENAMINE SYSTEM: SUBSTITUTION AT
CARBON 105
RESONANCE CONTRIBUTION TO KETONE AND AMIDE
TAUTOMERISM 107
U E FIELD-RESONANCE BALANCE IN VINYLOGOUS HETEROAROMATIC
AMIDINES 108
CONCLUSIONS 110
REFERENCES 111
THEORETICAL CONSIDERATION OF **-SOIUT*ON TAUTOMERIC EQUILIBRIA *N
RELATION T . DRUG DESIGN 113
PETER
*
. NAGY
INTRODUCTION 113
METHODOLOGY 114
GENERAL ISSUES 114
RELATIVE SOLVATION FREE ENERGY 115
CALCULATION OF THE EQUILIBRIUM CONSTANT 117
EQUILIBRATION MECHANISM 119
SWITCHING OF THE NONLINEAR OPTICAL RESPONSES OF AN* DERIVATIVES: FROM
DILUTE SOLUTIONS TO THE SOLID STATE 175
FREDERIC CASTET AND BENOIT CHAMPAGNE
INTRODUCTION 175
EXPERIMENTAL AND THEORETICAL METHODS 178
6.4 RELATION TO DRUG DESIGN 123
6.4.1 LIGAND BINDING 123
6.4.2 DRUG PARTITIONING 125
6.5 INSOLUTION EQUILIBRIUM CALCULATIONS 127
6.5.1 NEUTRAL SYSTEMS 128
6.5.1.1 HETEROCYCLIC TAUTOMERS 128
6.5.1.2 AMINO ACIDS AND AMINOPHENOLS 135
6.5.1.3 KETO-ENOL TAUTOMERISM 138
6.5.1.4 MISCELLANEOUS SYSTEMS 140
6.5.2 TAUTOMERIC PROTONATION 141
6.6 CONCLUDING REMARKS 142
REFERENCES 143
* DIRECT OBSERVATION AND CONTROL OF SINGLE-MOLECULE TAUTOMERIZATION BY
LOW-TEMPERATURE SCANNING TUNNELING MICROSCOPY 147
TAKASHI KUMAGAI AND LEONHARD GR
**
7.1 BRIEF INTRODUCTION TO STM 148
7.1.1 OPERATION PRINCIPLE OF STM 148
7.1.2 ^EORETICAL MODEL OF STM 149
7.1.3 SCANNING TUNNELING SPECTROSCOPY 149
7.1.4 INELASTIC ELECTRON TUNNELING PROCESS 151
7.2 DIRECT OBSERVATION OF SINGLE-MOLECULE TAUTOMERIZATION USING
STM 152
7.2.1 TAUTOMERIZATION WITHIN PORPHYRIN AND PHTHALOCYANINE
DERIVATIVES 152
7.2.2 TAUTOMERIZATION WITHIN A SINGLE PORPHYCENE MOLECULE 155
7.2.2.1 INTRODUCTION 155
7.2.2.2 ADSORPTION STRUCTURE OF A PORPHYCENE MOLECULE ON A CU(110)
SURFACE 156
7.2.2.3 THERMALLY INDUCED
C*S-C*S
TAUTOMERIZATION 157
7.2.2.4 STM-INDUCED
C*S-C*S
TAUTOMERIZATION 159
7.2.2.5 MECHANISM OF STM* INDUCED TAUTOMERIZATION 163
*
.2.2.6 CONTROL OF TAUTOMERIZATION WITH SINGLE COPPER
ATOMS 166
7.2.2
*
*
TAUTOMERIZATION OF INDIVIDUAL PORPHYCENE MOLECULES IN MOLECULAR
ASSEMBLIES 170
7.3 CONCLUDING REMARKS 172
ACKNOWLEDGMENTS 172
REFERENCES 172
8
1
2
8.:
8.:
8
.
2.1
8
.
2.2
8.2.3
8.2.4
8.3
8.3.1
8.3.2
8.3.3
8.4
9
9.1
* 9
9.3
Q I
9.5
9.6
10
10.1
10.2
10.3
10.4
11
11.1
11.2
NONLINEAR OPTICAL PROPERTIES OF MOLECULAR COMPOUNDS AND
SOLIDS 178
EXPERIMENTAL MEASUREMENTS OF QUADRATIC MOLECULAR
HYPERPOLARIZABILITIES 179
CALCULATIONS OF MOLECULAR QUADRATIC HYPERPOLARIZABILITIES 181
CALCULATIONS OF SECOND-ORDER NONLINEAR SUSCEPTIBILITIES OF
MOLECULAR SOLIDS 185
SECOND-ORDER NONLINEAR OPTICAL RESPONSES OF ANILS 187
NLO RESPONSES OF ANILS IN SOLUTION: STRUCTURE-PROPERTY
RELATIONSHIPS 187
SOLVENT EFFECTS ON THE NLO SWITCHING PROPERTIES OF ANILS 191
SWITCHING IN THE SOLID STATE: IMPACT OF INTERMOLECULAR INTERACTIONS
ON THE NLO RESPONSES 193
CONCLUSIONS 196
ACKNOWLEDGMENTS 197
REFERENCES 197
TAUTOMERISM IN OXOPORPH*RINOGENS AND PYRAZINACENES 203
JONATHAN P. HILL, JAN LABUTA, SHINSUKE ISHIHARA, GARYJ. RICHARDS,
YONGSHU
XIE, FRANCIS D SOUZA, AND KOTSUHIKO ARIGA
INTRODUCTION 203
TAUTOMERISM IN OXOPORPHYRINOGEN, OXP 205
MULTICHROMIC ACIDITY INDICATOR INVOLVING TAUTOMERISM 211
POLYTAUTOMERISM IN OXOCORROLOGEN
*
OXC 212
TAUTOMERISM IN LINEAR REDUCED FUSED 01IGO*L,*P*RAZINES
(PYRAZINACENES) 219
CONCLUSION 225
REFERENCES 226
ENOLIMINE-KETOENAMINE TAUTOMERISM FOR CHEMOSENSING 229
ALEXANDER D. DUBONOSOV, VLADIMIRA. BREN, AND VLADIMIR I. MINKIN
INTRODUCTION 229
PROTOTROPIC ENOLIMINE-KETOENAMINE TAUTOMERISM 229
IONOCHROMIC ENOLIMINE-KETOENAMINE TAUTOMERIC SYSTEMS FOR IONS
SENSING 234
CONCLUDING REMARKS 247
ACKNOWLEDGMENTS 247
REFERENCES 247
TAUTOMERIZABLE AZOPHENOL DYES: CORNERSTONES FOR ADVANCED
LIGHT-RESPONSIVE MATERIALS 253
JAUME GARCIA-AMOMS AND DOLORES VELASCO
AZOBENZENE-BASED LIGHT-SENSITIVE MATERIALS 253
AZOPHENOLS: TAUTOMERIZABIE PHOTOCHROMES WITH FAST SWITCHING
SPEEDS 255
11.2.1 D E RM A L ISOMERIZATION KINETICS OF AZOPHENOLS IN ISOTROPIC
SOLVENTS 256
11.2.2 THERMAL ISOMERIZATION KINETICS OF AZOPHENOLS IN
LIQUID-CRYSTALLINE
AND GLASSY MEDIA 259
11.3 SUB-MILLISECOND *ERM ALLY ISOMERIZING AZOPHENOLS FOR OPTICALLY
TRIGGERED OSCILLATING MATERIALS 262
11.4 FAST-RESPONDING ARTIFICIAL MUSCLES WITH AZOPHENOL-BASED LIQUID
SINGLE CRYSTAL ELASTOMERS 266
11.5 CONCLUSION 268
REFERENCES 269
12 CONTROLLED TAUTOMERISM: IS IT POSSIBLE? 273
DANIELA NEDELTCHEVO-ANTONOVA AND LIUDMIL ANTONOV
12.1 INTRODUCTION 273
12.2 MANIPULATION OF ELECTRONIC PROPERTIES OF THE SUBSTITUENTS 275
12.3 TAUTOMERIC TWEEZERS 278
12.4 TAUTOMERIC CAVITIES 279
12.5 PROTON CRANES 282
12.6 ROTARY SWITCHES 290
12.7 CONCLUDING REMARKS 291
ACKNOWLEDGMENTS 291
REFERENCES 291
13 SUPRAMOLECULAR CONTROL OVER TAUTOMERISM *N ORGANIC SOLIDS 295
KRUNOSLAV UZAREVIC,VLADIMIR STUINOVIC, AND ISAIRTA RUBCIC
13.1 CRYSTAL ENGINEERING AND TAUTOMERISM IN MOECULAR
SOIIDS 297
13.2 SUPRAMOLECULAR SYNTHONS 298
13.3 SOLID-STATE TAUTOMERISM, PROTON TRANSFER
*
AND HYDROGEN
BONDING 300
13.4 SUPRAMOLECULAR STABILIZATION OF METASTABLE TAUTOMERS 304
13.5 IDENTIFICATION OF TAUTOMERIC PROPERTIES AND CONNECTIVITY
PREFERENCES 305
13.6 SYNTHETIC METHODS 306
13.7 SUPRAMOLECULAR INTERACTIONS IN OTHER TAUTOMERIC SOLIDS 310
REFERENCES 324
14 PROTON TAUTOMERISM *N SYSTEMS OF INCREASING COMPLEXITY: EXAMPLES
FROM ORGANIC MOLECULES TO ENZYMES 329
HANS-HEINRICH LIMBACH, GLEB 5. DENISOV, LLYO G. SHENDEROVICH,
AND PETER R
**
.TO
*
ST
*
V
14.1 INTRODUCTION *
14.2 HYDROGEN BOND GEOMETRIES AND PROTON TRANSFER 330
14.3 TAUTOMERIZATIONS WITHOUT REQUIRING REORGANIZATION OF THE
ENVIRONMENT 333
EXAMPLES OF INTRAMOLECULAR TAUTOMERIZATIONS WITHOUT REQUIRING
REORGANIZATION OF THE ENVIRONMENT 334
14.3.2 EXAMPLES OF INTERMOLECULAR TAUTOMERIZATIONS IN THE ABSENCE OF
PRE-EQUILIBRIA WITHOUT REQUIRING MAJOR REORGANIZATION OF THE
ENVIRONMENT 338
14.3.3 EXAMPLES OF INTERMOLECULAR TAUTOMERIZATIONS IN THE PRESENCE OF
PRE-EQUILIBRIA WITHOUT REQUIRING MAJOR REORGANIZATION OF THE
ENVIRONMENT 340
14.3.4 MECHANISMS OF TAUTOMERIZATIONS WITHOUT REQUIRING REORGANIZATION
OF THE ENVIRONMENT 342
14.3.5 AN APPLICATION TO THE FUNCTION OF THE IMIDAZOLE RING OF HISTIDINE
64
IN HUMAN CARBONIC ANHYDRASE II 344
14.4 TAUTOMERIZATIONS REQUIRING REORGANIZATION OF THE
ENVIRONMENT 346
14.4.1 TAUTOMERIZATION OF CHARGED MOLECULES AND HYDROGEN BONDED
CLUSTERS 347
14.4.1.1 PROTON SPONGES 347
14.4.1.2 PHENOL-CARBOXYLATE VERSUS CARBOXYLIC ACID-PHENOLATE
COMPLEXES 351
14.4.1.3 HOMOCONJUGATED CARBOXYLIC ACID CARBOXYLATES 354
14.4.2 TAUTOMERIZATION OF NEUTRAL HETEROCYCLIC ACID-BASE
COMPLEXES 356
14.4.2.1 MODEL COMPLEXES OF THE ACID-PYRIDINE TYPE 356
14.4.2.2 MANNICH BASES 358
14.4.2.3 MODEL SCHIFF BASES 359
14.4.2.4 COFACTOR PYRIDOXAL ^ -PHOSPHATE: FROM ORGANIC MODELS TO
ALANINE RACEMASE AND ASPARTATE AMINOTRANSFERASE 360
14.5 CONCLUSIONS 364
ACKNOWLEDGMENTS 365
REFERENCES 365
INDEX 373
|
| any_adam_object | 1 |
| author2 | Antonov, Ljudmil 1966- |
| author2_role | edt |
| author2_variant | l a la |
| author_GND | (DE-588)1100173544 |
| author_facet | Antonov, Ljudmil 1966- |
| building | Verbundindex |
| bvnumber | BV043534546 |
| classification_rvk | VK 6000 |
| ctrlnum | (OCoLC)951527639 (DE-599)DNB1079291288 |
| dewey-full | 540 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 540 - Chemistry and allied sciences |
| dewey-raw | 540 |
| dewey-search | 540 |
| dewey-sort | 3540 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV043534546 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T07:28:13Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527339952 3527339957 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-028950162 |
| oclc_num | 951527639 |
| open_access_boolean | |
| owner | DE-11 DE-83 DE-19 DE-BY-UBM DE-355 DE-BY-UBR |
| owner_facet | DE-11 DE-83 DE-19 DE-BY-UBM DE-355 DE-BY-UBR |
| physical | XX, 377 Seiten Illustrationen, Diagramme |
| publishDate | 2016 |
| publishDateSearch | 2016 |
| publishDateSort | 2016 |
| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
| record_format | marc |
| spelling | Antonov, Ljudmil 1966- (DE-588)1100173544 edt Tautomerism concepts and applications in science and technology edited by Liudmil Antonov Weinheim, Germany Wiley-VCH Verlag GmbH & Co. KGaA [2016] © 2016 XX, 377 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Tautomerie (DE-588)4078171-9 gnd rswk-swf Chemie Chemistry Festkörperchemie Physical Chemistry Physical Organic Chemistry Physikalische Chemie Physikalische Organische Chemie Solid State Chemistry (DE-588)4143413-4 Aufsatzsammlung gnd-content Tautomerie (DE-588)4078171-9 s DE-604 Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-69574-4 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-69572-0 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-69573-7 Erscheint auch als Online-Ausgabe 978-3-527-69571-3 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028950162&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Tautomerism concepts and applications in science and technology Tautomerie (DE-588)4078171-9 gnd |
| subject_GND | (DE-588)4078171-9 (DE-588)4143413-4 |
| title | Tautomerism concepts and applications in science and technology |
| title_auth | Tautomerism concepts and applications in science and technology |
| title_exact_search | Tautomerism concepts and applications in science and technology |
| title_full | Tautomerism concepts and applications in science and technology edited by Liudmil Antonov |
| title_fullStr | Tautomerism concepts and applications in science and technology edited by Liudmil Antonov |
| title_full_unstemmed | Tautomerism concepts and applications in science and technology edited by Liudmil Antonov |
| title_short | Tautomerism |
| title_sort | tautomerism concepts and applications in science and technology |
| title_sub | concepts and applications in science and technology |
| topic | Tautomerie (DE-588)4078171-9 gnd |
| topic_facet | Tautomerie Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028950162&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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