Stable Radicals
Fundamentals and Applied Aspects of Odd-Electron Compounds
Herausgeber: Hicks, Robin
Stable Radicals
Fundamentals and Applied Aspects of Odd-Electron Compounds
Herausgeber: Hicks, Robin
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Stable radicals - molecules with odd electrons which are sufficiently long lived to be studied or isolated using conventional techniques - have enjoyed a long history and are of current interest for a broad array of fundamental and applied reasons, for example to study and drive novel chemical reactions, in the development of rechargeable batteries or the study of free radical reactions in the body. In Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds a team of international experts provide a broad-based overview of stable radicals, from the fundamental aspects of…mehr
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- Produktdetails
- Verlag: John Wiley & Sons / Wiley
- Seitenzahl: 624
- Erscheinungstermin: 9. August 2010
- Englisch
- Abmessung: 249mm x 193mm x 38mm
- Gewicht: 1315g
- ISBN-13: 9780470770832
- ISBN-10: 047077083X
- Artikelnr.: 27816706
- Verlag: John Wiley & Sons / Wiley
- Seitenzahl: 624
- Erscheinungstermin: 9. August 2010
- Englisch
- Abmessung: 249mm x 193mm x 38mm
- Gewicht: 1315g
- ISBN-13: 9780470770832
- ISBN-10: 047077083X
- Artikelnr.: 27816706
(Thomas T. Tidwell). 1.1 Introduction. 1.2 Free radical rearrangements. 1.3
Other routes to triphenylmethyl radicals. 1.4 The persistent radical
effect. 1.5 Properties of triphenylmethyl radicals. 1.6 Steric effects and
persistent radicals. 1.7 Substituted triphenylmethyl radicals and dimers.
1.8 Tris(heteroaryl)methyl and related triarylmethyl radicals. 1.9
Delocalized persistent radicals: analogues of triarylmethyl radicals. 1.10
Tetrathiatriarylmethyl (TAM) and related triarylmethyl radicals. 1.11
Perchlorinated triarylmethyl radicals. 1.12 Other triarylmethyl radicals.
1.13 Diradicals and polyradicals related to triphenylmethyl. 1.14 Outlook.
Acknowledgements. References. 2. Polychlorotriphenylmethyl Radicals:
Towards Multifunctional Molecular Materials (Jaume Veciana and Imma
Ratera). 2.1 Introduction. 2.2 Functional molecular materials based on PTM
radicals. 2.3 Multifunctional switchable molecular materials based on PTM
radicals. 2.4 Conclusions. 3. Phenalenyls, Cyclopentadienyls, and Other
Carbon-Centered Radicals (Yasushi Morita and Shinsuke Nishida). 3.1
Introduction. 3.2 Open shell graphene. 3.3 Phenalenyl. 3.4
2,5,8-Tri-tert-butylphenalenyl radical. 3.5 Perchlorophenalenyl radical.
3.6 Dithiophenalenyl radicals. 3.7 Nitrogen-containing phenalenyl systems.
3.8 Oxophenalenoxyl systems. 3.9 Phenalenyl-based zwitterionic radicals.
3.10 À-Extended phenalenyl systems. 3.11 Curve-structured phenalenyl
system. 3.12 Non-alternant stable radicals. 3.13 Stable triplet carbenes.
3.14 Conclusions. 4. The Nitrogen Oxides: Persistent Radicals and van der
Waals Complex Dimers (D. Scott Bohle). 4.1 Introduction. 4.2 Synthetic
access. 4.3 Physical properties. 4.4 Structural chemistry of the monomers
and dimers. 4.5 Electronic structure of nitrogen oxides. 4.6 Reactivity of
nitric oxide and nitrogen dioxide and their van der Waals complexes. 4.7
The kinetics of nitric oxide's termolecular reactions. 4.8 Biochemical and
organic reactions of nitric oxide. 4.9 General reactivity patterns. 4.10
The colored species problem in nitric oxide chemistry. 4.11 Conclusions. 5.
Nitroxide Radicals: Properties, Synthesis and Applications (Hakim Karoui,
Franc¿ois Le Moigne, Olivier Ouari and Paul Tordoi). 5.1 Introduction. 5.2
Nitroxide structure. 5.3 Nitroxide multiradicals. 5.4 Nitronyl nitroxides
(NNOs). 5.5 Synthesis of nitroxides. 5.6 Chemical properties of nitroxides.
5.7 Nitroxides in supramolecular entities. 5.8 Nitroxides for dynamic
nuclear polarization (DNP) enhanced NMR. 5.9 Nitroxides as pH-sensitive
spin probes. 5.10 Nitroxides as prefluorescent probes. 5.11 EPR-spin
trapping technique. 5.12 Conclusions. 6. The Only Stable Organic Sigma
Radicals: Di-tert-Alkyliminoxyls (Keith U. Ingold). 6.1 Introduction. 6.2
The discovery of stable iminoxyls. 6.3 Hydrogen atom abstraction by
di-tert-butyliminoxyl. 6.4 Other reactions and non-reactions of
di-tert-butyliminoxyl. 6.5 Di-tert-alkyliminoxyls more sterically crowded
than di-tert-butyliminoxyl. 6.6 Di-(1-Adamantyl)iminoxyl: a truly stable Ã
radical. 7. Verdazyls and Related Radicals Containing the Hydrazyl [R2N-NR]
Group (Robin G. Hicks). 7.1 Introduction. 7.2 Verdazyl radicals. 7.3
Tetraazapentenyl radicals. 7.4 Tetrazolinyl radicals. 7.5 1,2,4-Triazolinyl
radicals. 7.6 1,2,4,5-Tetrazinyl radicals. 7.7 Benzo-1,2,4-triazinyl
radicals. 7.8 Summary. 8. Metal Coordinated Phenoxyl Radicals (Fabrice
Thomas). 8.1 Introduction. 8.2 General properties of phenoxyl radicals. 8.3
Occurrence of tyrosyl radicals in proteins. 8.4 Complexes with coordinated
phenoxyl radicals. 8.5 Conclusions. 8.6 Abbreviations. 9. The Synthesis and
Characterization of Stable Radicals Containing the Thiazyl (SN) Fragment
and Their Use as Building Blocks for Advanced Functional Materials (Robin
G. Hicks). 9.1 Introduction. 9.2 Radicals based exclusively on sulfur and
nitrogen. 9.3 "Organothiazyl" radicals. 9.4 Thiazyl radicals as "advanced
materials". 9.5 Conclusions. 10. Stable Radicals of the Heavy p-Block
Elements (Jari Konu and Tristram Chivers). 10.1 Introduction. 10.2 Group 13
element radicals. 10.3 Group 14 element radicals. 10.4 Group 15 element
radicals. 10.5 Group 16 element radicals. 10.6 Group 17 element radicals.
10.7 Summary and future prospects. 11. Application of Stable Radicals as
Mediators in Living-Radical Polymerization (Andrea R. Szkurhan, Julie
Lukkarila and Michael K. Georges). 11.1 Introduction. 11.2 Living
polymerizations. 11.3 Stable free radical polymerization. 11.4.1
Triazolinyl radicals. 11.5 Aqueous stable free radical polymerization
processes. 11.6 The application of stable free radical polymerization to
new materials. 11.7 Conclusions. List of abbreviations. 12.
Nitroxide-Catalyzed Alcohol Oxidations in Organic Synthesis (Christian
Bruckner). 12.1 Introduction. 12.2 Mechanism of TEMPO-catalyzed alcohol
oxidations. 12.3 Nitroxides used as catalysts. 12.4 Chemoselectivity:
oxidation of primary vs secondary alcohols. 12.5 Chemoselectivity:
oxidation of primary vs benzylic alcohols. 12.6 Oxidation of secondary
alcohols to ketones. 12.7 Oxidations of alcohols to carboxylic acids. 12.8
Stereoselective nitroxide-catalyzed oxidations. 12.9 Secondary oxidants
used in nitroxide-catalyzed reactions. 12.10 Use of nitroxide-catalyzed
oxidations in tandem reactions. 12.11 Predictable side reactions. 12.12
Comparison with other oxidation methods. 12.13 Nitroxide-catalyzed
oxidations and green chemistry. 13. Metal-Nitroxide Complexes: Synthesis
and Magnetostructural Correlations (Victor Ovcharenko). 13.1 Introduction.
13.2 Two types of nitroxide for direct coordination of the metal to the
nitroxyl group. 13.3 Ferro- and ferrimagnets based on metal-nitroxide
complexes. 13.4 Heterospin systems based on polynuclear compounds of metals
with nitroxides. 13.5 Breathing crystals. 13.6 Other studies of
metal-nitroxides. 13.7 Conclusions. 14. Rechargeable Batteries Using Robust
but Redox Active Organic Radicals (Takeo Suga and Hiroyuki Nishide). 14.1
Introduction. 14.2 Redox reaction of organic radicals. 14.3 Mechanism and
performance of an organic radical battery. 14.4 Molecular design and
synthesis of redox active radical polymers. 14.5 A totally organic-based
radical battery. 14.6 Conclusions. 15. Spin Labeling: A Modern Perspective
(Lawrence J. Berliner). 15.1 Introduction. 15.2 The early years. 15.3
Advantages of nitroxides. 15.4 Applications of spin labeling to biochemical
and biological systems. 15.5 Distance measurements. 15.6 Site directed spin
labeling (SDSL): how is it done? 15.7 Other spin labeling applications.
15.8 Conclusions. 16. Functional in vivo EPR Spectroscopy and Imaging Using
Nitroxide and Trityl Radicals (Valery V. Khramtsov and Jay L. Zweier). 16.1
Introduction. 16.2 Nitroxyl radicals. 16.3 Triarylmethyl (trityl) radicals.
16.4 In vivo EPR oximetry using nitroxyl and trityl probes. 16.5 EPR
spectroscopy and imaging of pH using nitroxyl and trityl probes. 16.6
Redox- and thiol-sensitive nitroxide probes. 16.7 Conclusions. 17.
Biologically Relevant Chemistry of Nitroxides (Sara Goldstein and Amram
Samuni). 17.1 Introduction. 17.2 Mechanisms of nitroxide reactions with
biologically relevant small radicals. 17.3 Nitroxides as SOD mimics. 17.4
Nitroxides as catalytic antioxidants in biological systems. 17.5
Conclusions. Acknowledgements. References. Index.
(Thomas T. Tidwell). 1.1 Introduction. 1.2 Free radical rearrangements. 1.3
Other routes to triphenylmethyl radicals. 1.4 The persistent radical
effect. 1.5 Properties of triphenylmethyl radicals. 1.6 Steric effects and
persistent radicals. 1.7 Substituted triphenylmethyl radicals and dimers.
1.8 Tris(heteroaryl)methyl and related triarylmethyl radicals. 1.9
Delocalized persistent radicals: analogues of triarylmethyl radicals. 1.10
Tetrathiatriarylmethyl (TAM) and related triarylmethyl radicals. 1.11
Perchlorinated triarylmethyl radicals. 1.12 Other triarylmethyl radicals.
1.13 Diradicals and polyradicals related to triphenylmethyl. 1.14 Outlook.
Acknowledgements. References. 2. Polychlorotriphenylmethyl Radicals:
Towards Multifunctional Molecular Materials (Jaume Veciana and Imma
Ratera). 2.1 Introduction. 2.2 Functional molecular materials based on PTM
radicals. 2.3 Multifunctional switchable molecular materials based on PTM
radicals. 2.4 Conclusions. 3. Phenalenyls, Cyclopentadienyls, and Other
Carbon-Centered Radicals (Yasushi Morita and Shinsuke Nishida). 3.1
Introduction. 3.2 Open shell graphene. 3.3 Phenalenyl. 3.4
2,5,8-Tri-tert-butylphenalenyl radical. 3.5 Perchlorophenalenyl radical.
3.6 Dithiophenalenyl radicals. 3.7 Nitrogen-containing phenalenyl systems.
3.8 Oxophenalenoxyl systems. 3.9 Phenalenyl-based zwitterionic radicals.
3.10 À-Extended phenalenyl systems. 3.11 Curve-structured phenalenyl
system. 3.12 Non-alternant stable radicals. 3.13 Stable triplet carbenes.
3.14 Conclusions. 4. The Nitrogen Oxides: Persistent Radicals and van der
Waals Complex Dimers (D. Scott Bohle). 4.1 Introduction. 4.2 Synthetic
access. 4.3 Physical properties. 4.4 Structural chemistry of the monomers
and dimers. 4.5 Electronic structure of nitrogen oxides. 4.6 Reactivity of
nitric oxide and nitrogen dioxide and their van der Waals complexes. 4.7
The kinetics of nitric oxide's termolecular reactions. 4.8 Biochemical and
organic reactions of nitric oxide. 4.9 General reactivity patterns. 4.10
The colored species problem in nitric oxide chemistry. 4.11 Conclusions. 5.
Nitroxide Radicals: Properties, Synthesis and Applications (Hakim Karoui,
Franc¿ois Le Moigne, Olivier Ouari and Paul Tordoi). 5.1 Introduction. 5.2
Nitroxide structure. 5.3 Nitroxide multiradicals. 5.4 Nitronyl nitroxides
(NNOs). 5.5 Synthesis of nitroxides. 5.6 Chemical properties of nitroxides.
5.7 Nitroxides in supramolecular entities. 5.8 Nitroxides for dynamic
nuclear polarization (DNP) enhanced NMR. 5.9 Nitroxides as pH-sensitive
spin probes. 5.10 Nitroxides as prefluorescent probes. 5.11 EPR-spin
trapping technique. 5.12 Conclusions. 6. The Only Stable Organic Sigma
Radicals: Di-tert-Alkyliminoxyls (Keith U. Ingold). 6.1 Introduction. 6.2
The discovery of stable iminoxyls. 6.3 Hydrogen atom abstraction by
di-tert-butyliminoxyl. 6.4 Other reactions and non-reactions of
di-tert-butyliminoxyl. 6.5 Di-tert-alkyliminoxyls more sterically crowded
than di-tert-butyliminoxyl. 6.6 Di-(1-Adamantyl)iminoxyl: a truly stable Ã
radical. 7. Verdazyls and Related Radicals Containing the Hydrazyl [R2N-NR]
Group (Robin G. Hicks). 7.1 Introduction. 7.2 Verdazyl radicals. 7.3
Tetraazapentenyl radicals. 7.4 Tetrazolinyl radicals. 7.5 1,2,4-Triazolinyl
radicals. 7.6 1,2,4,5-Tetrazinyl radicals. 7.7 Benzo-1,2,4-triazinyl
radicals. 7.8 Summary. 8. Metal Coordinated Phenoxyl Radicals (Fabrice
Thomas). 8.1 Introduction. 8.2 General properties of phenoxyl radicals. 8.3
Occurrence of tyrosyl radicals in proteins. 8.4 Complexes with coordinated
phenoxyl radicals. 8.5 Conclusions. 8.6 Abbreviations. 9. The Synthesis and
Characterization of Stable Radicals Containing the Thiazyl (SN) Fragment
and Their Use as Building Blocks for Advanced Functional Materials (Robin
G. Hicks). 9.1 Introduction. 9.2 Radicals based exclusively on sulfur and
nitrogen. 9.3 "Organothiazyl" radicals. 9.4 Thiazyl radicals as "advanced
materials". 9.5 Conclusions. 10. Stable Radicals of the Heavy p-Block
Elements (Jari Konu and Tristram Chivers). 10.1 Introduction. 10.2 Group 13
element radicals. 10.3 Group 14 element radicals. 10.4 Group 15 element
radicals. 10.5 Group 16 element radicals. 10.6 Group 17 element radicals.
10.7 Summary and future prospects. 11. Application of Stable Radicals as
Mediators in Living-Radical Polymerization (Andrea R. Szkurhan, Julie
Lukkarila and Michael K. Georges). 11.1 Introduction. 11.2 Living
polymerizations. 11.3 Stable free radical polymerization. 11.4.1
Triazolinyl radicals. 11.5 Aqueous stable free radical polymerization
processes. 11.6 The application of stable free radical polymerization to
new materials. 11.7 Conclusions. List of abbreviations. 12.
Nitroxide-Catalyzed Alcohol Oxidations in Organic Synthesis (Christian
Bruckner). 12.1 Introduction. 12.2 Mechanism of TEMPO-catalyzed alcohol
oxidations. 12.3 Nitroxides used as catalysts. 12.4 Chemoselectivity:
oxidation of primary vs secondary alcohols. 12.5 Chemoselectivity:
oxidation of primary vs benzylic alcohols. 12.6 Oxidation of secondary
alcohols to ketones. 12.7 Oxidations of alcohols to carboxylic acids. 12.8
Stereoselective nitroxide-catalyzed oxidations. 12.9 Secondary oxidants
used in nitroxide-catalyzed reactions. 12.10 Use of nitroxide-catalyzed
oxidations in tandem reactions. 12.11 Predictable side reactions. 12.12
Comparison with other oxidation methods. 12.13 Nitroxide-catalyzed
oxidations and green chemistry. 13. Metal-Nitroxide Complexes: Synthesis
and Magnetostructural Correlations (Victor Ovcharenko). 13.1 Introduction.
13.2 Two types of nitroxide for direct coordination of the metal to the
nitroxyl group. 13.3 Ferro- and ferrimagnets based on metal-nitroxide
complexes. 13.4 Heterospin systems based on polynuclear compounds of metals
with nitroxides. 13.5 Breathing crystals. 13.6 Other studies of
metal-nitroxides. 13.7 Conclusions. 14. Rechargeable Batteries Using Robust
but Redox Active Organic Radicals (Takeo Suga and Hiroyuki Nishide). 14.1
Introduction. 14.2 Redox reaction of organic radicals. 14.3 Mechanism and
performance of an organic radical battery. 14.4 Molecular design and
synthesis of redox active radical polymers. 14.5 A totally organic-based
radical battery. 14.6 Conclusions. 15. Spin Labeling: A Modern Perspective
(Lawrence J. Berliner). 15.1 Introduction. 15.2 The early years. 15.3
Advantages of nitroxides. 15.4 Applications of spin labeling to biochemical
and biological systems. 15.5 Distance measurements. 15.6 Site directed spin
labeling (SDSL): how is it done? 15.7 Other spin labeling applications.
15.8 Conclusions. 16. Functional in vivo EPR Spectroscopy and Imaging Using
Nitroxide and Trityl Radicals (Valery V. Khramtsov and Jay L. Zweier). 16.1
Introduction. 16.2 Nitroxyl radicals. 16.3 Triarylmethyl (trityl) radicals.
16.4 In vivo EPR oximetry using nitroxyl and trityl probes. 16.5 EPR
spectroscopy and imaging of pH using nitroxyl and trityl probes. 16.6
Redox- and thiol-sensitive nitroxide probes. 16.7 Conclusions. 17.
Biologically Relevant Chemistry of Nitroxides (Sara Goldstein and Amram
Samuni). 17.1 Introduction. 17.2 Mechanisms of nitroxide reactions with
biologically relevant small radicals. 17.3 Nitroxides as SOD mimics. 17.4
Nitroxides as catalytic antioxidants in biological systems. 17.5
Conclusions. Acknowledgements. References. Index.