Tautomerism: methods and theories
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2014
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| ISBN: | 3527332944 9783527332946 |
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| 245 | 1 | 0 | |a Tautomerism |b methods and theories |c ed. by Liudmil Antonov |
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Datensatz im Suchindex
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| adam_text |
VII
CONTENTS
PREFACE
XV
LIST OF CONTRIBUTORS XIX
1
TAUTOMERISM: INTRODUCTION, HISTORY, AND RECENT DEVELOPMENTS
IN EXPERIMENTAL AND THEORETICAL METHODS 1
PETER J. TAYLOR, GERT VAN DER ZWAN, AND LIUDMIL ANTONOV
1.1 THE DEFINITION AND SCOPE OFTAUTOMERISM: PRINCIPLES AND
PRACTICALITIES
1
1.2
CAUSES OF REVERSAL IN TAUTOMERIC FORM: AROMATIC RESONANCE 3
1.3 CAUSES OF REVERSAL IN TAUTOMERIC FORM: LONE-PAIR AND DIPOLAR
REPULSION 4
1.4 CAUSES OF REVERSAL IN TAUTOMERIC FORM: SELECTIVE STABILIZATION
THROUGH "FAR" INTRAMOLECULAR HYDROGEN
BONDING 5
1.5 CHANGES IN TAUTOMERIC FORM BROUGHT ABOUT BY ELECTRONEGATIVE
SUBSTITUENTS 7
1.6 THE INFLUENCE OF SOLVENT ON TAUTOMERIC FORM
8
1.7 TAUTOMERIC EQUILIBRIUM: HISTORICAL OVERVIEW OF AN ANALYTICAL
PROBLEM
9
1.8
SHORT HISTORICAL OVERVIEW OF TAUTOMERIZATION DYNAMICS 13
1.9 CONCLUSIONS AND OUTLOOK 19
REFERENCES 20
2
ABSORPTION UV-VIS SPECTROSCOPY AND CHEMOMETRICS: FROM QUALITATIVE
CONCLUSIONS TO QUANTITATIVE ANALYSIS 25
LIUDMIL ANTONOV
2.1 INTRODUCTION 25
2.2
QUANTITATIVE ANALYSIS OF TAUTOMERIC EQUILIBRIA 26
2.2.1 CLASSICAL SPECTROPHOTOMETRIC ANALYSIS, LIMITATIONS, AND EARLY
ATTEMPTS TO FIND A SOLUTION 26
2.2.2 QUANTITATIVE ANALYSIS BY USING BANDS DECOMPOSITION 29
2.2.3 CHANGE IN THE ENVIRONMENT AFFECTS THE EQUILIBRIUM: PHYSICAL
MEANING AND MATHEMATICAL EXPRESSION
33
HTTP://D-NB.INFO/1036281116
VIII
CONTENTS
2.3
ANALYSIS OF REAL TAUTOMERIC SYSTEMS 37
2.3.1 KETO-ENOL TAUTOMERISM IN 4-(PHENYLDIAZENYL)NAPHTHALEN-L-OL:
SOLVENT EFFECT 37
2.3.2 KETO-ENOL TAUTOMERISM IN L-((PHENYLIMINO)METHYL)NAPHTHALEN-2-OL:
VERIFICATION OF THE APPROACH
40
2.3.3 KETO-ENOL TAUTOMERISM IN L-(PHENYLDIAZENYL)NAPHTHALEN-2-OL AND
L-((PHENYLIMINO)METHYL)NAPHTHALEN-2-OL: EFFECTS OF THE TEMPERATURE
AND THE STRENGTH OF INTRAMOLECULAR HYDROGEN BONDING 41
2.3.4
AMMONIUM-AZONIUM TAUTOMERISM IN
4-((4-AMINOPHENYL)DIAZENYL)-N,N-DIMETHYLANILINE: EFFECT OF
PROTONATION AND SOLVENT
43
2.4
CONCLUDING REMARKS 46
REFERENCES
46
3
STUDIES OF PHOTOINDUCED NH TAUTOMERISM BY STATIONARY AND
TIME-RESOLVED FLUORESCENCE TECHNIQUES 49
ALEXANDER KYRYCHENKO, JERZY HERBICH, AND JACEK WALUK
3.1 INTRODUCTION 49
3.2
PHOTOINDUCED PROTON/HYDROGEN ATOM TRANSFER 50
3.2.1 DIRECT INTRAMOLECULAR PROTON TRANSFER REACTIONS 50
3.2.2 SOLVENT-MEDIATED NH TAUTOMERISM 52
3.3 FLUORESCENCE TECHNIQUES FOR STUDYING TAUTOMERISM 52
3.3.1
STEADY-STATE FLUORESCENCE METHODS 52
3.3.2 TIME-RESOLVED FLUORESCENCE APPROACHES 54
3.3.3 ADVANCED TECHNIQUES IN FLUORESCENCE SPECTROSCOPY 54
3.3.3.1 FLUORESCENCE ANISOTROPY 54
3.3.3.2 FLUORESCENCE MICROSCOPY AND FLUORESCENCE CORRELATION
SPECTROSCOPY
55
3.4
TAUTOMERISM IN BIFUNCTIONAL NH/N AZAAROMATICS 56
3.4.1 INTRAMOLECULAR NH/N TAUTOMERIZATION 56
3.4.2 INTERMOLECULAR NH/N TAUTOMERIZATION IN HYDROGEN-BONDED
DIMERS 59
3.4.3 TAUTOMERIZATION IN SOLUTE-SOLVENT HYDROGEN-BONDED
COMPLEXES
60
3.5
AB INITIO AND DFT COMPUTATIONAL METHODS 67
3.5.1 REACTION MECHANISMS AND COOPERATIVITY IN PROTON
MIGRATIONS 67
3.5.1.1 CONCERTED VERSUS STEPWISE MECHANISM 67
3.5.2 REACTION PATH CALCULATIONS AND ENERGY BARRIERS FOR PROTON
TRANSFER
69
3.5.3
CHALLENGES FOR MOLECULAR DYNAMICS AND QM/MM SIMULATIONS 71
3.6 NH TAUTOMERISM AS A TOOL IN BIOPHYSICS 72
3.7 CONCLUDING REMARKS 74
ACKNOWLEDGMENT
74
REFERENCES 75
CONTENTS
IX
4
FEMTOSECOND PUMP-PROBE SPECTROSCOPY OF PHOTOINDUCED
TAUTOMERISM 79
STEFAN LOCHBRUNNER
4.1
INTRODUCTION 79
4.2
ULTRAFAST PUMP-PROBE SPECTROSCOPY 81
4.2.1 TIME-RESOLVED ABSORPTION MEASUREMENTS 82
4.2.2 FLUORESCENCE UPCONVERSION 84
4.2.3 IONIZATION TECHNIQUES 84
4.2.4 TIME-RESOLVED INFRARED SPECTROSCOPY 84
4.3 DYNAMICS FROM PUMP-PROBE SPECTROSCOPY 85
4.3.1 ULTRAFAST TRANSIENT ABSORPTION SIGNATURES OF ESIPT 85
4.3.2 DATA ANALYSIS 87
4.3.3
BALLISTIC WAVEPACKET MOTION
88
4.3.4 COHERENTLY EXCITED VIBRATIONS IN PRODUCT MODES 90
4.3.5 ULTRAFAST IR STUDIES 92
4.3.6
OTHER TAUTOMERIC REACTIONS 92
4.4 REACTION MECHANISM 93
4.5
REACTION-PATH-SPECIFIC WAVEPACKET DYNAMICS IN DOUBLE ESIPT 96
4.6 INTERNAL CONVERSION 97
4.7
SUMMARY AND CONCLUSIONS 99
ACKNOWLEDGMENTS 100
REFERENCES 100
5
NMR SPECTROSCOPIC STUDY OF TAUTOMERISM IN SOLUTION AND
IN THE SOLID STATE 103
ERICH KLEINPETER
5.1 INTRODUCTION 103
5.2
METHODOLOGIES OF NMR SPECTROSCOPY TO STUDY TAUTOMERISM 104
5.3 TYPES OF TAUTOMERISM STUDIED BY NMR SPECTROSCOPY 109
5.3.1 RING-CHAIN TAUTOMERISM 109
5.3.2 TETRAZOLE-AZIDE TAUTOMERISM 111
5.3.3
TRANSANNULAR TAUTOMERISM 111
5.3.4 KETO-ENOL TAUTOMERISM 112
5.3.5 IMINE-AMINE TAUTOMERISM 116
5.3.6 LACTAM-LACTIM TAUTOMERISM 124
5.3.7 ANNULAR TAUTOMERISM OF FIVE- OR SIX-MEMBERED HETEROCYCLIC
COMPOUNDS
126
5.3.8
NITROSO (N-OXIDE)-OXIME TAUTOMERISM 128
5.3.9 TAUTOMERIC STRUCTURES IN NUCLEOSIDES, NUCLEOTIDES, AND PROTEINS
129
5.3.10 TAUTOMERISM IN PORPHYRINS 131
5.3.11 CARBOHYDRATE TAUTOMERISM 132
5.3.12
AZO-HYDRAZONE TAUTOMERISM 133
5.3.13 TAUTOMERISM OF PHOSPHORUS COMPOUNDS 134
5.3.14 MISCELLANEOUS TAUTOMERISMS 136
5.4 CONCLUSIONS AND OUTLOOK 137
X I
CONTENTS
ACKNOWLEDGMENTS
138
REFERENCES 138
6
ISOTOPE EFFECTS ON CHEMICAL SHIFTS AS A TOOL IN THE STUDY OF
TAUTOMERIC EQUILIBRIA 145
POUL ERIK HANSEN
6.1 INTRODUCTION 145
6.2
EXPERIMENTAL REQUIREMENTS 148
6.2.1 ONE-TUBE EXPERIMENTS 148
6.2.2 EXCHANGE OF ISOTOPES 149
6.2.3 CONCENTRIC TUBES 149
6.2.4 COUPLINGS 149
6.2.5
PRIMARY ISOTOPE EFFECTS 149
6.2.6 TEMPERATURE 150
6.2.7
VARIATION OF SOLVENT 150
6.2.8 ISOTOPE LABELING 151
6.3 ISOTOPE EFFECTS ON CHEMICAL SHIFTS 151
6.3.1 INTRINSIC ISOTOPE EFFECTS 151
6.3.1.1 INTRINSIC DEUTERIUM ISOTOPE EFFECTS ON
13
C CS 153
6.3.1.2 INTRINSIC DEUTERIUM ISOTOPE EFFECTS ON
IS
N CHEMICAL SHIFTS 154
6.3.1.3 DEUTERIUM ISOTOPE EFFECTS ON
17
0 CHEMICAL SHIFTS 154
6.3.1.4 DEUTERIUM ISOTOPE EFFECTS ON
19
F CS 154
6.3.1.5
18
0 ISOTOPE EFFECTS ON
13
C CHEMICAL SHIFTS 155
6.4 SECONDARY EQUILIBRIUM ISOTOPE EFFECTS ON CS 156
6.4.1 ISOTOPIC PERTURBATION OF EQUILIBRIUM 160
6.5 PRIMARY ISOTOPE EFFECTS 161
6.6
SOLID STATE 164
6.7
THEORETICAL CALCULATIONS 165
6.8 EXAMPLES 166
6.8.1
P -THIOXOKETONES 166
6.8.2 MULTIPLE EQUILIBRIA 169
6.9 OVERVIEW 172
REFERENCES
173
7
TAUTOMER-SELECTIVE SPECTROSCOPY OF NUDEOBASES, ISOLATED
IN THE GAS PHASE 177
MATTANJAH S. DE VRIES
7.1 INTRODUCTION 177
7.2
TECHNIQUES 177
7.3
GUANINE 179
7.4
ADENINE 187
7.5
CYTOSINE 187
7.6
URACIL AND THYMINE 188
7.7
BASE PAIRS 189
7.8
OUTLOOK 191
CONTENTS
| XI
ACKNOWLEDGMENTS
192
REFERENCES 192
8
DIRECT EVIDENCE OF SOLID-STATE TAUTOMERISM BY DIFFRACTION METHODS:
ISOMERS, EQUILIBRIA, AND KINETICS 197
PANTE NAUMOV AND SUBASH CHANDRA SAHOO
8.1 APPLICATION OF X-RAY DIFFRACTION TO STUDY TAUTOMERISM 197
8.2 EXAMPLES OF X-RAY DIFFRACTION ANALYSIS OF PROTON TRANSFER 199
8.2.1 TAUTOMERISM, PROTON TRANSFER, AND RESONANCE-ASSISTED HYDROGEN
BONDING
199
8.2.2
EXAMPLES OF THERMALLY INDUCED TAUTOMERISM 203
8.2.3 PHOTOINDUCED TAUTOMERIC PROCESSES 208
8.3 OTHER DIFFRACTION METHODS USED TO STUDY PROTON TRANSFER
REACTIONS 211
REFERENCES
211
9
DYNAMICS OF GROUND- AND EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER
REACTIONS 213
GERT VAN DER ZWAN
9.1 INTRODUCTION 213
9.2
TRANSITION STATE THEORY 216
9.3 TWO EXAMPLES OFTAUTOMERIZATION 218
9.4 THE ROLE OF THE SOLVENT 221
9.5
SOLVENT FRICTION AND SOLVENT DYNAMICS 224
9.6 THE SOLVENT COORDINATE: BASICS 226
9.7 POLARIZATION FLUCTUATIONS 229
9.8 THE SOLVENT COORDINATE: AN APPLICATION 231
9.9 ELECTRONIC REARRANGEMENT 233
9.10 THE RUG THAT TIES THE (CLASSICAL) ROOM TOGETHER 234
9.11 QUANTUM AND CLASSICAL 236
9.12
QUANTUM DECAY 239
9.13
COUPLING QUANTUM AND CLASSICAL MOTION: A SIMPLE EXAMPLE 242
9.14 NONLINEAR OPTICS 246
9.15
FEMTOCHEMISTRY 247
9.16 CONCLUDING REMARKS 249
REFERENCES 250
10
FORCE FIELD TREATMENT OF PROTON AND HYDROGEN TRANSFER IN
MOLECULAR SYSTEMS 253
JING HUANG AND MARKUS MEUWLY
10.1 INTRODUCTION 253
10.2
COMPUTATIONAL APPROACHES TO PROTON TRANSFER 254
10.3 PROTON TRANSFER REACTIONS WITH MMPT 256
10.4 APPLICATIONS OF MMPT 259
10.4.1 INFRARED SPECTROSCOPY 259
XII
| CONTENTS
10.4.2
CLASSICAL AND QUANTUM PROTON TRANSFER IN THE GAS PHASE 261
10.4.3 CONDENSED-PHASE PROTON TRANSFER 263
10.4.4 MMPT FOR NMR PROPERTIES 264
10.5 DISCUSSION AND OUTLOOK 267
ACKNOWLEDGMENTS
268
REFERENCES 268
11
THE SCOPE AND LIMITATIONS OF LSER IN THE STUDY OFTAUTOMER RATIO 277
PETER J. TAYLOR
11.1 INTRODUCTION 277
11.2
THE TAFT-KAMLET LSER METHODOLOGY 277
11.2.1 THE** SCALE 278
11.2.2 THE 0 SCALE 279
11.2.3
THE A SCALE 281
11.2.4
THE P VALUE FOR WATER 283
11.2.5 7I* FOR THE GAS PHASE 286
11.3 LSER CASE HISTORIES IN THE FIELD OFTAUTOMERISM 287
11.3.1 ENOL FORMATION FROM /3-DIKETONES AND RELATED COMPOUNDS 288
11.3.2
TAUTOMERISM IN SCHIFF BASES AND RELATED AZO COMPOUNDS 292
11.3.3 THREE-WAY TAUTOMERISM IN THE PYRAZOLONE 25 295
11.4 OVERVIEW 298
APPENDIX 11.
A: EARLIER APPROACHES 301
REFERENCES 302
12
THE "BASICITY METHOD" FOR ESTIMATING TAUTOMER RATIO: A RADICAL
RE-APPRAISAL 305
PETER J. TAYLOR
12.1 INTRODUCTION 305
12.2
EXPERIMENTAL PROTOCOL 307
12.3 THE DERIVATION OF CORRECTION FACTORS 308
12.3.1 AMIDINES AND RELATED COMPOUNDS 308
12.3.2 CONFORMATIONAL EFFECTS ON AMIDINE CORRECTION FACTORS 309
12.3.3 LACTAMS: SIMULTANEOUS DETERMINATION OF A(NME) AND A(OME) 310
12.3.4 VINYLOGOUS LACTAMS: SIMULTANEOUS ESTIMATION OF A(NME) AND
A(OME)
312
12.3.5
A(NME) IN ACYLAMIDINES AND IMIDES 313
12.3.6 A(NME) FOR COMPOUNDS WITH CONTIGUOUS NITROGEN ATOMS 315
12.3.7 A(NME) FOR THIOLACTAMS AND THEIR VINYLOGUES 317
12.3.8 AN ATTEMPT AT A(SME) FOR THIOLACTAMS AND THEIR VINYLOGUES 319
12.3.9
CORRECTION FACTORS: SUMMARY AND SPECULATIONS 320
12.4 REGULARITIES REVEALED BY CORRECTION FACTORS 320
12.4.1 BENZOFUSION TO GIVE BENZENOID STRUCTURES IN SIX-MEMBERED RING
OXOHETEROCYDES 321
12.4.2
BENZOFUSION TO GIVE QUINONOID STRUCTURES IN A VARIETY OF
COMPOUNDS 324
CONTENTS
I XIII
12.5
COMPLICATING FACTORS IN THE USE OF THE "BASICITY METHOD" 326
12.5.1 COMPLICATIONS CAUSED BY STERIC AND STEREOELECTRONIC FACTORS 326
12.5.2 COMPLICATIONS CAUSED BY HYDROGEN BONDING 327
12.5.3 COMPLICATIONS CAUSED BY PROTONATION AT THE "WRONG SITE" 328
12.6 TAUTOMERIC PROBLEMS TO WHICH THE "BASICITY METHOD"
IS INAPPLICABLE
330
12.7
OVERVIEW 332
REFERENCES
333
13
QUANTUM CHEMICAL CALCULATION OFTAUTOMERIC EQUILIBRIA 337
WALTER M.F. FABIAN
13.1 INTRODUCTION 337
13.2
COMPUTATIONAL PROCEDURES 338
13.2.1 WAVE-FUNCTION-BASED METHODS 338
13.2.1.1 INDEPENDENT PARTICLE METHODS 339
13.2.1.2 CORRELATED TREATMENTS 340
13.2.2
DENSITY FUNCTIONAL PROCEDURES 342
13.2.2.1 OVERVIEW OF DENSITY FUNCTIONALS 343
13.2.2.2 VALIDATION OF DENSITY FUNCTIONALS 346
13.2.3 CHOICE OF BASIS SET 347
13.2.4 CALCULATION OF SPECTROSCOPIC PROPERTIES 351
13.3 SOLVENT EFFECTS 353
13.3.1
CONTINUUM SOLVATION MODELS 353
13.3.2 EXPLICIT SOLVENT MODELS 355
13.4 APPLICATIONS OF QUANTUM CHEMICAL METHODS TO TAUTOMERIC
EQUILIBRIA 357
13.4.1 THE SAMPL2 CHALLENGE OF PREDICTING TAUTOMER RATIOS 357
13.4.2
LACTAM-LACTIMTAUTOMERISMOF2-HYDROXYPYRIDINE 360
13.4.3 ANNULAR TAUTOMERISM IN TETRAZOLE 363
13.5 CONCLUDING REMARKS 363
REFERENCES 364
INDEX
369 |
| any_adam_object | 1 |
| author2 | Antonov, Ljudmil 1966- |
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| author_GND | (DE-588)1100173544 |
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| building | Verbundindex |
| bvnumber | BV041475067 |
| classification_rvk | VK 6000 VK 6001 |
| classification_tum | CHE 615f |
| ctrlnum | (OCoLC)876817828 (DE-599)DNB1036281116 |
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| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 540 - Chemistry and allied sciences 541 - Physical chemistry |
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| discipline | Chemie / Pharmazie Chemie |
| format | Book |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV041475067 |
| illustrated | Illustrated |
| indexdate | 2025-03-10T13:01:20Z |
| institution | BVB |
| isbn | 3527332944 9783527332946 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-026921140 |
| oclc_num | 876817828 |
| open_access_boolean | |
| owner | DE-11 DE-91S DE-BY-TUM DE-19 DE-BY-UBM |
| owner_facet | DE-11 DE-91S DE-BY-TUM DE-19 DE-BY-UBM |
| physical | XX, 377 S. graph. Darst. 244 mm x 170 mm |
| publishDate | 2014 |
| publishDateSearch | 2014 |
| publishDateSort | 2014 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Tautomerism methods and theories ed. by Liudmil Antonov Weinheim Wiley-VCH 2014 XX, 377 S. graph. Darst. 244 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Tautomerie (DE-588)4078171-9 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Tautomerie (DE-588)4078171-9 s b DE-604 Antonov, Ljudmil 1966- (DE-588)1100173544 edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4369758&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026921140&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Tautomerism methods and theories Tautomerie (DE-588)4078171-9 gnd |
| subject_GND | (DE-588)4078171-9 (DE-588)4143413-4 |
| title | Tautomerism methods and theories |
| title_auth | Tautomerism methods and theories |
| title_exact_search | Tautomerism methods and theories |
| title_full | Tautomerism methods and theories ed. by Liudmil Antonov |
| title_fullStr | Tautomerism methods and theories ed. by Liudmil Antonov |
| title_full_unstemmed | Tautomerism methods and theories ed. by Liudmil Antonov |
| title_short | Tautomerism |
| title_sort | tautomerism methods and theories |
| title_sub | methods and theories |
| topic | Tautomerie (DE-588)4078171-9 gnd |
| topic_facet | Tautomerie Aufsatzsammlung |
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