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Encyclopedia of Radicals in Chemistry, Biology and Materials

ISBN: 978-0-470-97125-3
2324 pages
February 2012
Encyclopedia of Radicals in Chemistry, Biology and Materials (0470971258) cover image
Highlighting the growing applications of free radicals in key chemical, biological and medical processes

Over the last two decades the application of free radicals in organic synthesis, materials science and life science has steadily increased, this Encyclopedia presents methodologies and mechanisms  involving free radicals of chemical and biological research, including applications in materials science and medicine.

The aim of this Encyclopedia is to offer for the first time a description of free radicals within an interdisciplinary and multidisciplinary context, connecting structural characteristics and chemical properties to their applications in different areas of chemistry and related disciplines.

It covers not only basic concepts and chemical synthesis, but also touches on various aspects concerning the role of free radicals in materials and life sciences. The reader will find a balanced contribution of topics related to free radicals covering for example, their role in proteomics, genomics and lipidomics as well as their enormous potential in synthesis and technology.

Covers topical areas such as:

  • Alzheimer's disease and antioxidants in food within medicine and life sciences
  • Synthesis and catalysis, combustion and atmospheric chemistry within chemistry
  • Ageing and signalling in biological processes

Of interest to anybody working in the field of free radicals in the broadest sense. It will address scientists who want to enter the interdisciplinary field of free radicals. In particular, it is aimed primarily at chemists and life science researchers who want to gain a wider and deeper understanding of free radicals which will allow them to apply free radicals in their own scientific field.

The book consists of four themed volumes:

  • Basic Concepts & Methodologies
  • Synthetic Strategies & Applications
  • Chemical Biology
  • Polymers & Materials

Online Edition
Encyclopedia of Radicals in Chemistry, Biology and Materials is also available online, click here for more details: http://onlinelibrary.wiley.com/book/10.1002/9781119953678

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VOLUME 1: BASIC CONCEPTS AND METHODOLOGIES

Preface ix

List of Contributors xi

Abbreviations and Acronymns xix

1 The History of Free Radical Chemistry 1
Thomas T. Tidwell

2 Overview of Radical Initiation 37
Jacques Lalevée and Jean Pierre Fouassier

3 Basic Concepts on Radical Chain Reactions 57
Michael S. Sherburn

4 Thermochemistry and Hydrogen Transfer Kinetics 81
Andreas A. Zavitsas

5 Radical Kinetics and Clocks 107
Martin Newcomb

6 Radical Rearrangements: Ester-Substituted Radicals and Hydrogen Atom Migrations 125
Kaname Sasaki, Ian Cumpstey and David Crich

7 Analysis of Radicals by EPR 147
John C. Walton

8 Structures and Reactivity of Radicals Followed by Magnetic Resonance 175
Alexandra Yurkovskaya, Olga Morozova and Georg Gescheidt

9 Matrix Isolation of Radicals 207
Artur Mardyukov and Wolfram Sander

10 Supramolecular Radical Chemistry 229
Marco Lucarini

11 Redox Properties of Radicals 249
David C. Magri and Mark S. Workentin

12 Photo Induced Radical Reactions 275
Julia P´erez-Prieto and Miguel A. Miranda

13 Radical Cation/Anion and Neutral Radicals: A Comparison 301
Amber N. Hancock and J. M. Tanko

14 The SRN1 Reaction 333
Javier I. Bardagí, Victoria A. Vaillard and Roberto A. Rossi

15 Photoinduced Reactions of Radical Ions via Charge Separation 365
Shunichi Fukuzumi and Kei Ohkubo

16 Radiation-Induced Radical Reactions 395
Krzysztof Bobrowski

17 Free Radical Chemistry in Room-Temperature Ionic Liquids 433
Ilya A. Shkrob and James F. Wishart

18 Radical Stability—Thermochemical Aspects 449
Johnny Hioe and Hendrik Zipse

19 Radical Chemistry in the Gas Phase 477
Christian Alcaraz, Ingo Fischer and Detlef Schröder

20 Atmospheric Radical Chemistry 503
Paul H. Wine and J. Michael Nicovich

VOLUME 2: SYNTHETIC STRATEGIES AND APPLICATIONS

21 Tin Hydrides and Functional Group Transformations 529
Hannelore Jasch and Markus R. Heinrich

22 Silanes as Reducing Reagents in Radical Chemistry 561
Chryssostomos Chatgilialoglu and Vitaliy I. Timokhin

23 Boron in Radical Chemistry 601
Philippe Renaud

24 Intramolecular Homolytic Substitutions in Synthesis 629
Sara H. Kyne and Carl H. Schiesser

25 Stereoselective Radical Reactions 655
Yong-Hua Yang and Mukund P. Sibi

26 Unusual Cyclizations 693
Kerry Gilmore and Igor V. Alabugin

27 Radical Cascade Reactions 729
Alexandre Baralle, Abdulkader Baroudi, Marion Daniel, Louis Fensterbank, Jean-Philippe Goddard, Emmanuel Lacôte, Marie-Hélène Larraufie, Giovanni Maestri, Max Malacria and Cyril Ollivier

28 Main-Group Elements in Radical Chemistry 767
Alexandre Baralle, Abdulkader Baroudi, Marion Daniel, Louis Fensterbank, Jean-Philippe Goddard, Emmanuel Lacôte, Marie-Hélène Larraufie, Giovanni Maestri, Max Malacria and Cyril Ollivier

29 Organic Electron Donors 817
John A. Murphy

30 Organic Synthesis Using Samarium Diiodide 849
Susannah C. Coote, Robert A. Flowers II, Troels Skrydstrup and David J. Procter

31 Manganese(III) Acetate, CAN, and Fe(III) Salts in Oxidative Radical Chemistry 901
Jonathan W. Burton

32 Halogen and Chalcogen Transfer Chemistry 943
Chaozhong Li

33 Xanthates and Related Derivatives as Radical Precursors 965
Samir Z. Zard

34 Epoxides in Titanocene-Mediated and -Catalyzed Radical Reactions 989
Andreas Gansäuer and André Fleckhaus

35 Transition Metals and Radicals 1003
Hideki Yorimitsu

36 Unusual Radical Acceptors 1019
Piero Spagnolo and Daniele Nanni

37 Radical Arylations 1059
Santiago E. Vaillard and Armido Studer

38 Nitroxides in Synthetic Radical Chemistry 1095
Chittreeya Tansakul and Rebecca Braslau

39 Radicals and Carbohydrates 1131
Inés Pérez-Martín and Ernesto Suárez

40 Electrochemically Initiated Radical Reactions 1175
Martin A. Bohn, Anna Paul and Gerhard Hilt

41 Synthetic Radical Photochemistry 1217
Emmanuel Riguet and Norbert Hoffmann

42 Radical Chemistry by Using Flow Microreactor Technology 1243
Takahide Fukuyama and Ilhyong Ryu

VOLUME 3: CHEMICAL BIOLOGY

43 Biological Chemistry of Reactive Oxygen Species 1259
Christine C. Winterbourn

44 Reactions of Small Reactive Species with DNA 1283
Nicholas E. Geacintov and Vladimir Shafirovich

45 Oxidatively Generated Nucleobase Modifications in Isolated and Cellular DNA 1319
Jean Cadet, Thierry Douki, Didier Gasparutto, Jean-Luc Ravanat and J. Richard Wagner

46 Oxidatively Formed Sugar Radicals in Nucleic Acids 1345
Thanasis Gimisis and Chryssostomos Chatgilialoglu

47 Understanding DNA Radicals Employing Theory and Electron Spin Resonance Spectroscopy 1371
Amitava Adhikary, Anil Kumar, David Becker and Michael D. Sevilla

48 Charge Transfer in DNA 1397
Mamoru Fujitsuka and Tetsuro Majima

49 Oxidative Damage to Proteins 1425
Michael J. Davies

50 Radical-Based Damage of Sulfur-Containing Amino Acid Residues 1459
Christian Schöneich

51 Electron Transfer in Peptides and Proteins 1475
Bernd Giese, Sonja Eckhardt and Miriam Lauz

52 Radical Enzymes 1501
Wolfgang Buckel and Bernard T. Golding

53 Theoretical Studies of Radical Enzymes 1547
Gregory M. Sandala, David M. Smith and Leo Radom

54 Lipid Peroxidation 1577
Etsuo Niki

55 Lipid Isomerization 1599
Carla Ferreri and Chryssostomos Chatgilialoglu

56 Antioxidants in Chemistry and Biology 1623
Luca Valgimigli and Derek A. Pratt

57 Free Radicals and Metabolic Disorders 1679
Guy Cohen, Yael Riahi and Shlomo Sasson

VOLUME 4: POLYMERS AND MATERIALS

58 Radical Polymerization in Industry 1701
Peter Nesvadba

59 Kinetics of Polymerizations 1737
Michael Buback and Gregory T. Russell

60 Fundamentals of Controlled/Living Radical Polymerization 1785
Krzysztof Matyjaszewski

61 Nitroxide-Mediated Polymerization and its Applications 1813
Didier Gigmes and Sylvain R. A. Marque

62 Atom Transfer Radical Polymerization (ATRP) and Addition (ATRA) and Applications 1851
Tomislav Pintauer and Krzysztof Matyjaszewski

63 Reversible Addition Fragmentation Chain Transfer (RAFT) Polymerization: Mechanism, Process and Applications 1895
Christopher Barner-Kowollik, James P. Blinco, Mathias Destarac, Kristofer J. Thurecht and S´ebastien Perrier

64 Sb, Bi, Te, and I-Transfer Polymerization and Applications 1931
Shigeru Yamago and Eiichi Kayahara

65 Spin Labels and Spin Probes 1965
David Bardelang, Mica¨el Hardy, Olivier Ouari and Paul Tordo

66 Radical Thiol–X Click Chemistry 2017
Niels ten Brummelhuis and Helmut Schlaad

67 Conducting Polymers: Applications in Electronics and Photovoltaics 2057
Huanli Dong and Wenping Hu

68 Silicon Radical Surface Chemistry 2081
Bart Rijksen, Mabel A. Caipa Campos, Jos M. J. Paulusse and Han Zuilhof

69 Persistent and Stable Silyl Radicals 2117
Boris Tumanskii, Miriam Karni and Yitzhak Apeloig

70 Physical Properties of Thiazyl Radicals Toward Conductive and Magnetic Materials 2147
Kunio Awaga

71 Polyradicals in Batteries 2163
Kenichi Oyaizu and Hiroyuki Nishide

72 Radical Chemistry on Fullerenes 2171
Manolis D. Tzirakis and Michael Orfanopoulos

73 A Paradigm for the Radical-Mediated Photochemical Synthesis of Metal Nanostructures 2197
Juan C. Scaiano, Kevin G. Stamplecoskie, Katherine L. McGilvray and Natalia L. Pacioni

Author Index 2211

Subject Index

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Named CHOICE Outstanding Title for 2012

“This set is an indispensable addition for academic libraries, whether in print form, or for many libraries in its electronic version.  Summing Up: Highly recommended.  Academic libraries supporting lower-level undergraduates and above.”  (Choice, 1 July  2012)

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