Related Titles -- Title Page -- Copyright -- Table of Contents -- List of Contributors -- Preface -- References -- Chapter 1: Tautomerism: A Historical Perspective -- 1.1 Thermodynamic Aspects -- 1.2 Kinetic Aspects -- 1.3 Conclusions -- References -- Chapter 2: "Triage" for Tautomers: The Choice between Experiment and Computation -- 2.1 Introduction (Original Text Written by Peter J. Taylor) -- 2.2 cis-Amides -- 2.3 Tautomerism in Alicyclic Lactams: Six-Membered Rings -- 2.4 Tautomerism in Alicyclic Lactams: 2-Pyrrolidinone -- 2.5 Tautomerism in Other Five-Membered Ring Lactams -- 2.6 Tautomeric Ratios Requiring Computation: Alicyclic β-Diketones -- 2.7 Tautomeric Ratios Requiring Computation: "Maleic Hydrazide" -- 2.8 Tautomer Ratios Requiring Computation: 2-Oxo Derivatives of Pyrrole, Furan, and Thiazole -- 2.9 Tautomeric Ratios Requiring Computation: Compounds Containing Contiguous Carbonyl Groups -- 2.10 Tautomeric Ratios Requiring Computation: Compounds Containing Contiguous π-Donors -- 2.11 Compounds Equally Suited to Experiment or Computation: "Azapentalenes" -- 2.12 Phenomena Susceptible to Experiment or Computation: Lone Pair Effects -- 2.13 Conformational Effects on Aminoenone Stability: A Computational Approach -- 2.14 Overview (Original Text Written by Peter J. Taylor) -- References -- Chapter 3: Methods to Distinguish Tautomeric Cases from Static Ones -- 3.1 Introduction -- 3.2 The Liquid State -- 3.3 UV/VIS Spectroscopy -- 3.4 Infra Red Spectroscopy -- 3.5 Tautomerism in the Excited State -- 3.6 Near-Edge X-Ray -- 3.7 Energy-Dispersive X-Ray -- 3.8 Solid State -- 3.9 Single Molecule Tautomerization -- 3.10 Gas Phase -- 3.11 Theoretical Calculations -- References -- Chapter 4: Electron-Transfer-Induced Tautomerizations -- 4.1 Introduction -- 4.2 Methodology -- 4.3 O-Alkyl Phenyl Ketones -- 4.4 Conclusions -- Acknowledgments.

References -- Chapter 5: The Fault Line in Prototropic Tautomerism -- 5.1 Introduction: "N-Type" and "C-Type" Tautomerism -- 5.2 Tautomerism in Symmetrical Amidines -- 5.3 Tautomer Ratio in Asymmetric Heteroaromatic Amidines -- 5.4 Tautomer Ratio in the Imine-Enamine System: Substitution at Nitrogen -- 5.5 Tautomer Ratio in the Imine-Enamine System: Substitution at Carbon -- 5.6 The Resonance Contribution to Ketone and Amide Tautomerism -- 5.7 The Field-Resonance Balance in Vinylogous Heteroaromatic Amidines -- 5.8 Conclusions -- References -- Chapter 6: Theoretical Consideration of In-Solution Tautomeric Equilibria in Relation to Drug Design -- 6.1 Introduction -- 6.2 Methodology -- 6.3 Equilibration Mechanism -- 6.4 Relation to Drug Design -- 6.5 In-solution Equilibrium Calculations -- 6.6 Concluding Remarks -- References -- Chapter 7: Direct Observation and Control of Single-Molecule Tautomerization by Low-Temperature Scanning Tunneling Microscopy -- 7.1 Brief Introduction to STM -- 7.2 Direct Observation of Single-Molecule Tautomerization Using STM -- 7.3 Concluding Remarks -- Acknowledgments -- References -- Chapter 8: Switching of the Nonlinear Optical Responses of Anil Derivatives: From Dilute Solutions to the Solid State -- 8.1 Introduction -- 8.2 Experimental and Theoretical Methods -- 8.3 Second-Order Nonlinear Optical Responses of Anils -- 8.4 Conclusions -- Acknowledgments -- References -- Chapter 9: Tautomerism in Oxoporphyrinogens and Pyrazinacenes -- 9.1 Introduction -- 9.2 Tautomerism in Oxoporphyrinogen, OxP -- 9.3 Multichromic Acidity Indicator Involving Tautomerism -- 9.4 Polytautomerism in Oxocorrologen, OxC -- 9.5 Tautomerism in Linear Reduced Fused Oligo-1,4-pyrazines (Pyrazinacenes) -- 9.6 Conclusion -- References -- Chapter 10: Enolimine-Ketoenamine Tautomerism for Chemosensing -- 10.1 Introduction.

10.2 Prototropic Enolimine-Ketoenamine Tautomerism -- 10.3 Ionochromic Enolimine-Ketoenamine Tautomeric Systems for Ions Sensing -- 10.4 Concluding Remarks -- Acknowledgments -- References -- Chapter 11: Tautomerizable Azophenol Dyes: Cornerstones for Advanced Light-Responsive Materials -- 11.1 Azobenzene-Based Light-Sensitive Materials -- 11.2 Azophenols: Tautomerizable Photochromes with Fast Switching Speeds -- 11.3 Sub-Millisecond Thermally Isomerizing Azophenols for Optically Triggered Oscillating Materials -- 11.4 Fast-Responding Artificial Muscles with Azophenol-Based Liquid Single Crystal Elastomers -- 11.5 Conclusion -- References -- Chapter 12: Controlled Tautomerism: Is It Possible? -- 12.1 Introduction -- 12.2 Manipulation of Electronic Properties of the Substituents -- 12.3 Tautomeric Tweezers -- 12.4 Tautomeric Cavities -- 12.5 Proton Cranes -- 12.6 Rotary Switches -- 12.7 Concluding Remarks -- Acknowledgments -- References -- Chapter 13: Supramolecular Control over Tautomerism in Organic Solids -- 13.1 Crystal Engineering and Tautomerism in Molecular Solids -- 13.2 Supramolecular Synthons -- 13.3 Solid-State Tautomerism, Proton Transfer, and Hydrogen Bonding -- 13.4 Supramolecular Stabilization of Metastable Tautomers -- 13.5 Identification of Tautomeric Properties and Connectivity Preferences -- 13.6 Synthetic Methods -- 13.7 Supramolecular Interactions in Other Tautomeric Solids -- References -- Chapter 14: Proton Tautomerism in Systems of Increasing Complexity: Examples from Organic Molecules to Enzymes -- 14.1 Introduction -- 14.2 Hydrogen Bond Geometries and Proton Transfer -- 14.3 Tautomerizations without Requiring Reorganization of the Environment -- 14.4 Tautomerizations Requiring Reorganization of the Environment -- 14.5 Conclusions -- Acknowledgments -- References -- Index -- End User License Agreement.