Spectroscopy and Computation of Hydrogen-Bonded Systems

543 Pages·2023·15.828 MB·English

by  Wójcik M.J., Ozaki Y.

SpectroscopyandComputationofHydrogen-BondedSystems
Spectroscopy and Computation of
Hydrogen-Bonded Systems
Edited by Marek J. Wójcik and Yukihiro Ozaki
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Prof.em.YukihiroOzaki
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v
Contents
PartI Theory 1
1 LinearResponseTheoryApplicationstoIRSpectraof
H-BondedCyclicDimersTakingintoAccounttheSurrounding.
UpdatingContributionsInvolvingDavydovCoupling,Fermi
ResonancesandElectricalAnharmonicity 3
PaulBlaiseandOlivierHenri-Rousseau
1.1 Introduction 3
1.2 DimerStrongAnharmonicCouplingTheory 3
1.2.1 DifferentTheoreticalSituations 3
1.2.1.1 StrongAnharmonicCouplingWithinAdiabaticApproximationFor
Monomer 3
1.2.1.2 IntroductionofFermiResonances 6
1.2.1.3 H-BondedCentrosymmetricDimer 8
1.2.1.4 DimerInvolvingDamping,DavydovCoupling,andFermi
Resonances 12
1.2.2 TheSpectralDensity 13
1.3 ComparisonwithExperiments 14
1.3.1 CarboxylicAcidDimersIgnoringFermiResonances 14
1.3.1.1 GaseousandLiquidAceticAcidDimers 14
1.3.1.2 GaseousAcrylicandPropynoicAcids 15
1.3.2 CarboxylicAcidsTakingIntoAccountFermiResonances 16
1.3.2.1 CrystallineAdipicAcid 16
1.3.2.2 CrystallinePolarizedandUnpolarizedGlutaricAcidTakingInto
AccountFermiResonances 17
1.3.2.3 CrystallineThiopheneaceticAcidandThiopheneacrylicAcids 17
1.3.2.4 l.2-NaphtylaceticAcid(2-NA)Crystals 20
1.3.2.5 CrystallineAspirinDimersInvolvingSlowModeMorsePotential 23
1.3.2.6 PhthalicandTerephthalicAcidCrystals 25
1.3.2.7 LiquidFormicAcidMixingofMonomerandDimer 27
vi Contents
1.3.2.8 CrystallineFuroicAcidDimerwithSlowModeMorsePotentialand
FermiResonances 28
1.3.2.9 OtherKindsofH-BondedCompounds 31
1.3.2.10 PhosphinicAcidDimer 31
1.3.2.11 Monomerof(CH ) O···HCl 33
3 2
1.4 Conclusion 36
1.5 Acknowledgment 36
References 36
2 DynamicInteractionsShapingVibrationalSpectraof
Hydrogen-BondedSystems 39
MarekJ.Wójcik,MateuszBrela,ŁukaszBoda,MarekBoczar,andTakahito
Nakajima
2.1 Introduction 39
2.2 TheoreticalModeloftheInfraredSpectraofGaseous(CH ) O-HCland
3 2
(CH ) O-HFComplexes 42
3 2
2.3 SimulationoftheCl–H(D)andF–HStretchingBandsinthe
DME-H(D)ClandDME-HFComplexes 45
2.4 MethodologyofMolecularDynamics 47
2.5 SpectroscopicStudyofUracil,1-Methyluracil,and
1-Methyl-4-thiouracil 49
2.6 HydrogenBondInteractionDynamicsintheAdenineandThymine
Crystals 50
2.7 GuanineandCytosineCrystals 51
2.8 SpectroscopicSignatureforFerroelectricIce 52
2.9 Conclusions 55
Acknowledgment 56
References 56
3 TrajectoryOn-the-FlyMolecularDynamicsApproachto
TunnelingSplittingintheElectronicGroundandExcited
States 67
TetsuyaTaketsuguandYusukeOotani
3.1 Introduction 67
3.2 SemiclassicalTunnelingApproach 69
3.3 ResultsandDiscussion 71
3.3.1 UmbrellaInversionofAmmonia 72
3.3.2 IntramolecularHydrogenTransferinMalonaldehyde 73
3.3.3 ExcitedStateIntramolecularHydrogenTransferinTropolone 75
3.4 Conclusions 79
Acknowledgments 79
References 80
Contents vii
PartII Spectroscopy 83
4 SpectroscopicSignaturesofLow-BarrierHydrogenBondingin
NeutralSpecies 85
LidorFoguel,ZacharyN.Vealey,andPatrickH.Vaccaro
4.1 Introduction 85
4.2 SpectroscopicMetricsforHydrogenBonding 87
4.2.1 ContinuumofHydrogenBonding 87
4.2.2 RelationshiptoTunneling 92
4.2.3 Ground-StatePropertiesofModelSystems 93
4.2.4 Excited-StateSpectroscopyof6-Hydroxy-2-Formylfulvene 98
4.2.5 Ground-StateSpectroscopyof6-Hydroxy-2-Formylfulvene 102
4.2.6 Excited-StatePropertiesofModelSystems 105
4.3 ConcludingRemarks 108
Acknowledgments 109
References 109
5 Hydrogen-BondingInteractionsUsingExcess
Spectroscopy 123
YaqianWangandZhiwuYu
5.1 IntroductionofHydrogenBond 123
5.1.1 DefinitionofHydrogenBond 123
5.1.2 TheCriteriaoftheExistenceofHydrogenBonds 124
5.1.3 TheStrengthofHydrogenBonds 125
5.2 TheoryofExcessspectroscopy 126
5.3 StudiesofHydrogenBondsbyExcessIR 129
5.3.1 ClassicalHydrogenBonds 129
5.3.2 ChargeAssistedHydrogenBonds 131
5.3.3 CooperativeResonance-AssistedHydrogenBonds 134
5.3.4 Weak/ModerateHydrogenBonds 138
References 142
6 IntramolecularHydrogenBondinginPorphyrinIsomers 145
JacekWaluk
6.1 Introduction 145
6.2 H-BondCharacteristics 146
6.2.1 Porphine(1) 147
6.2.2 Porphycene(2) 148
6.2.3 Hemiporphycene(3) 150
6.2.4 Corrphycene(4) 152
6.2.5 Isoporphycene(5) 154
6.2.6 Porphyrin-(2.2.0.0)(6) 156
viii Contents
6.2.7 Porphyrin-(3.1.0.0)(7) 157
6.2.8 Porphyrin-(4.0.0.0)(8) 158
6.2.9 Inverted/ConfusedPorphyrin(9) 162
6.2.10 Neo-confusedPorphyrin(10) 164
6.3 CorrelationsBetweenGeometryandHBStrength 165
6.4 ParametersThatCanDescribetheHBStrength 167
6.5 TautomerizationMechanisms 168
6.6 Summary 169
Acknowledgments 170
References 170
7 IsotopeEffectsinHydrogenBondResearch 173
PoulErikHansen
7.1 Introduction 173
7.2 HydrogenBondPotentials 173
7.3 Calculations 175
7.4 HydrogenBondTypes 176
7.5 DeuteriumIsotopeEffectsonChemicalShifts 176
7.6 IntramolecularHydrogenBonds 177
7.6.1 Two-BondDeuteriumIsotopeEffectson13CChemicalShifts 178
7.6.2 Long-RangeIsotopeEffects 184
7.6.3 One-BondDeuteriumIsotopeEffectson15NChemicalShiftsin
Solution 185
7.7 BiologicalSystems 185
7.7.1 Proteins 185
7.7.2 DeuteriumIsotopeEffectson1HChemicalShifts 187
7.8 IntermolecularHydrogenBonds 187
7.9 PrimaryIsotopeEffects 189
7.10 IsotopeEffectsandAcidity 191
7.10.1 IsotopeEffectstoDetermineProtonationStates 191
7.11 SolventIsotopeEffectsandExchangeRates 192
7.12 ExchangeintheSolid-State 192
7.13 HydrogenBondEnergies 193
7.14 Tautomerism 194
7.15 Solid-StateNMR 197
7.15.1 DeuteriumIsotopeEffectson15NChemicalShifts 199
7.16 Conclusions 202
References 203
8 IntramolecularHydrogenBonding:ShapingConformers’
StructureandStability 213
GulceO.IldizandRuiFausto
8.1 Introduction 213
Contents ix
8.2 TheHalogen-SubstitutedAceticAcidsCF COOH,CCl COOH,and
3 3
CBr OOH:ImplicationsofIMHBonStructureandConformers’
3
Stabilities 215
8.3 TheSignificanceofIMHBintheorthoChloro-andFluoro-Substituted
BenzoicAcids 219
8.4 IMHBinThiotropolone:SculpturingtheBidirectionalInfrared-Induced
Bond-Breaking/Bond-FormingTautomerization 225
8.5 Conclusion 228
Acknowledgments 229
References 229
9 HydrogenBondingfromPerspectiveofOvertonesand
CombinationModes:Near-InfraredSpectroscopicStudy 233
MirosławA.Czarnecki,YusukeMorisawa,andYukihiroOzaki
9.1 Introduction 233
9.2 InvestigationofHydrogenBondingofWaterbyNIRSpectroscopy 235
9.3 TheChainLengthEffectontheDegreeofSelf-associationof
1-Alcohols 237
9.4 CombinedNIRandDielectricStudyonAssociationof1-Hexanolin
n-Hexane 240
9.5 NIRStudiesofMicroheterogeneityinAlcohol/Alcoholand
Alcohol/AlkaneBinaryMixtures 241
9.6 OvertonesofνC≡NVibrationasaProbeofMolecularStructureof
Nitriles 244
9.7 WeakHydrogenBondinPoly(3-Hydroxybutyrate)(PHB)StudiedbyNIR
Spectroscopy 246
9.8 StudiesofHydrogenBondingByUseofHigherOvertones 249
9.9 ComparisonofHydrogenBondingEffectsandSolventEffectsonWave
numbersandIntensitiesoftheFundamentalandFirstOvertoneofthe
N–HStretchingModeofPyrroleStudiedByNIR/IRSpectroscopyand
One-DimensionalVibrationalSchrödingerEquationApproach 252
9.10 Summary 256
Acknowledgments 257
References 257
10 DirectObservationandKineticMappingofPoint-to-Point
ProtonTransferofaHydroxy-PhotoacidtoMultiple
(Competing)IntramolecularProtonationSites 261
DinaPines,DanEliovich,DanielAminov,MarkSigalov,DanHuppert,and
EhudPines
10.1 Introduction 261
10.2 FromIntermolecularProtonTransfertoSolventtoIntramolecular
Point-to-PointTransferin1:1Hydrogen-BondingComplexesofWater
withBifunctionalOHPhotoacids 270
x Contents
10.3 WaterIsAbletoDonateandAcceptanH-bondasDemonstratedbyIR
Absorptionin1:1Water–(AcidorBase)Complexes 273
10.4 ProtonTransferAlongwithWaterBridgesinAcetonitrile(ACN)
SpanningtheDistanceBetweenanAcidicandaBasicSideGroupsof
BifunctionalPhotoacids 274
10.5 Time-ResolvedFluorescenceMeasurementsofProtonTransferalong
withWaterBridges 277
10.6 IsotopeD/HEffect 283
10.7 InsightsintotheMechanismofProtonTransferThroughOne-Water
BridgeinBifunctional2-Naphthols 285
10.8 Summary 288
Acknowledgments 289
References 289
11 SpectroscopicDeterminationofHydrogenBond
Energies 293
MausumiGoswamiandElangannanArunan
11.1 Introduction 293
11.2 BindingEnergyMeasurementInvolvingInfrared(IR)Excitation 296
11.2.1 MeasurementoftheDissociationEnergyofH-BondedComplexes
ThroughVibrationalPre-dissociationDynamicsviaInfrared
Excitation 296
11.2.1.1 OptothermalBolometricDetermination 297
11.2.1.2 VelocityMapImaging 299
11.2.2 DeterminationofGibbsFreeEnergyofH-BondedComplexFormation
ByInfraredSpectroscopy 307
11.2.3 MeasurementofBindingEnergyofH-BondedComplexesbyIR–UV
DoubleResonanceSpectroscopy 314
11.3 DeterminationoftheBindingEnergyofH-BondedComplexesUsing
SpectroscopicTechniquesInvolvingElectronicExcitation 316
11.3.1 DeterminationofH-BondDissociationEnergyThroughMultiphoton
IonizationTechniques 316
11.3.2 DeterminationoftheDissociationEnergyofCationicH-Bonded
ComplexesThroughBirge–SponerExtrapolation 325
11.3.3 DeterminationoftheDissociationEnergyofH-BondedComplexesUsing
SEP-REMPITechnique 328
11.4 EstimationoftheWellDepthofH-BondingInteractionsThrough
MicrowaveSpectroscopy 332
11.5 Conclusion 335
References 336
12 IRandNMRSpectralDiagnosticsofHydrogenBondEnergy
andGeometry 345
PeterM.TolstoyandElenaYu.Tupikina
12.1 Introduction 345