Encyclopedia of Radicals in Chemistry, Biology and Materials

Chryssostomos Chatgilialoglu was born in 1952 in Greece and studied at the University of Bologna, Italy. He was a postdoctoral fellow at the University of York, England, from 1977 to 1979 with Prof. ROC Norman, and from 1979 until 1982 he worked with Prof. KU Ingold at the National Research Council of Canada (Ottawa) as a research associate. In 1983 he returned to Italy to the Consiglio Nazionale delle Ricerche CNRS, Bologna, where he has been director of research?since 1991. His research focuses on free radical chemistry with current interests in mechanistic studies of biological processes. Armido Studer was born in Switzerland and made his studies at ETH in Zurich. He currently works as a Professor of Organic Chemistry at the Westfälische Wilhelms-Universität, Münster. His research interests focuses on the development of new synthetic methods in the field of free radical chemistry and more recently in the area of homogeneous catalysis.

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)

• VOLUME 1: BASIC CONCEPTS AND METHODOLOGIES Preface ixList of Contributors xiAbbreviations and Acronymns xix1 The History of Free Radical Chemistry 1Thomas T. Tidwell2 Overview of Radical Initiation 37Jacques Lalevée and Jean Pierre Fouassier3 Basic Concepts on Radical Chain Reactions 57Michael S. Sherburn4 Thermochemistry and Hydrogen Transfer Kinetics 81Andreas A. Zavitsas5 Radical Kinetics and Clocks 107Martin Newcomb6 Radical Rearrangements: Ester-Substituted Radicals and Hydrogen Atom Migrations 125Kaname Sasaki, Ian Cumpstey and David Crich7 Analysis of Radicals by EPR 147John C. Walton8 Structures and Reactivity of Radicals Followed by Magnetic Resonance 175Alexandra Yurkovskaya, Olga Morozova and Georg Gescheidt9 Matrix Isolation of Radicals 207Artur Mardyukov and Wolfram Sander10 Supramolecular Radical Chemistry 229Marco Lucarini11 Redox Properties of Radicals 249David C. Magri and Mark S. Workentin12 Photo Induced Radical Reactions 275Julia P´erez-Prieto and Miguel A. Miranda13 Radical Cation/Anion and Neutral Radicals: A Comparison 301Amber N. Hancock and J. M. Tanko14 The SRN1 Reaction 333Javier I. Bardagí, Victoria A. Vaillard and Roberto A. Rossi15 Photoinduced Reactions of Radical Ions via Charge Separation 365Shunichi Fukuzumi and Kei Ohkubo16 Radiation-Induced Radical Reactions 395Krzysztof Bobrowski17 Free Radical Chemistry in Room-Temperature Ionic Liquids 433Ilya A. Shkrob and James F. Wishart18 Radical Stability—Thermochemical Aspects 449Johnny Hioe and Hendrik Zipse19 Radical Chemistry in the Gas Phase 477Christian Alcaraz, Ingo Fischer and Detlef Schröder20 Atmospheric Radical Chemistry 503Paul H. Wine and J. Michael NicovichVOLUME 2: SYNTHETIC STRATEGIES AND APPLICATIONS21 Tin Hydrides and Functional Group Transformations 529Hannelore Jasch and Markus R. Heinrich22 Silanes as Reducing Reagents in Radical Chemistry 561Chryssostomos Chatgilialoglu and Vitaliy I. Timokhin23 Boron in Radical Chemistry 601Philippe Renaud24 Intramolecular Homolytic Substitutions in Synthesis 629Sara H. Kyne and Carl H. Schiesser25 Stereoselective Radical Reactions 655Yong-Hua Yang and Mukund P. Sibi26 Unusual Cyclizations 693Kerry Gilmore and Igor V. Alabugin27 Radical Cascade Reactions 729Alexandre Baralle, Abdulkader Baroudi, Marion Daniel, Louis Fensterbank, Jean-Philippe Goddard, Emmanuel Lacôte, Marie-Hélène Larraufie, Giovanni Maestri, Max Malacria and Cyril Ollivier28 Main-Group Elements in Radical Chemistry 767Alexandre Baralle, Abdulkader Baroudi, Marion Daniel, Louis Fensterbank, Jean-Philippe Goddard, Emmanuel Lacôte, Marie-Hélène Larraufie, Giovanni Maestri, Max Malacria and Cyril Ollivier29 Organic Electron Donors 817John A. Murphy30 Organic Synthesis Using Samarium Diiodide 849Susannah C. Coote, Robert A. Flowers II, Troels Skrydstrup and David J. Procter31 Manganese(III) Acetate, CAN, and Fe(III) Salts in Oxidative Radical Chemistry 901Jonathan W. Burton32 Halogen and Chalcogen Transfer Chemistry 943Chaozhong Li33 Xanthates and Related Derivatives as Radical Precursors 965Samir Z. Zard34 Epoxides in Titanocene-Mediated and -Catalyzed Radical Reactions 989Andreas Gansäuer and André Fleckhaus35 Transition Metals and Radicals 1003Hideki Yorimitsu36 Unusual Radical Acceptors 1019Piero Spagnolo and Daniele Nanni37 Radical Arylations 1059Santiago E. Vaillard and Armido Studer38 Nitroxides in Synthetic Radical Chemistry 1095Chittreeya Tansakul and Rebecca Braslau39 Radicals and Carbohydrates 1131Inés Pérez-Martín and Ernesto Suárez40 Electrochemically Initiated Radical Reactions 1175Martin A. Bohn, Anna Paul and Gerhard Hilt41 Synthetic Radical Photochemistry 1217Emmanuel Riguet and Norbert Hoffmann42 Radical Chemistry by Using Flow Microreactor Technology 1243Takahide Fukuyama and Ilhyong RyuVOLUME 3: CHEMICAL BIOLOGY43 Biological Chemistry of Reactive Oxygen Species 1259Christine C. Winterbourn44 Reactions of Small Reactive Species with DNA 1283Nicholas E. Geacintov and Vladimir Shafirovich45 Oxidatively Generated Nucleobase Modifications in Isolated and Cellular DNA 1319Jean Cadet, Thierry Douki, Didier Gasparutto, Jean-Luc Ravanat and J. Richard Wagner46 Oxidatively Formed Sugar Radicals in Nucleic Acids 1345Thanasis Gimisis and Chryssostomos Chatgilialoglu47 Understanding DNA Radicals Employing Theory and Electron Spin Resonance Spectroscopy 1371Amitava Adhikary, Anil Kumar, David Becker and Michael D. Sevilla48 Charge Transfer in DNA 1397Mamoru Fujitsuka and Tetsuro Majima49 Oxidative Damage to Proteins 1425Michael J. Davies50 Radical-Based Damage of Sulfur-Containing Amino Acid Residues 1459Christian Schöneich51 Electron Transfer in Peptides and Proteins 1475Bernd Giese, Sonja Eckhardt and Miriam Lauz52 Radical Enzymes 1501Wolfgang Buckel and Bernard T. Golding53 Theoretical Studies of Radical Enzymes 1547Gregory M. Sandala, David M. Smith and Leo Radom54 Lipid Peroxidation 1577Etsuo Niki55 Lipid Isomerization 1599Carla Ferreri and Chryssostomos Chatgilialoglu56 Antioxidants in Chemistry and Biology 1623Luca Valgimigli and Derek A. Pratt57 Free Radicals and Metabolic Disorders 1679Guy Cohen, Yael Riahi and Shlomo SassonVOLUME 4: POLYMERS AND MATERIALS58 Radical Polymerization in Industry 1701Peter Nesvadba59 Kinetics of Polymerizations 1737Michael Buback and Gregory T. Russell60 Fundamentals of Controlled/Living Radical Polymerization 1785Krzysztof Matyjaszewski61 Nitroxide-Mediated Polymerization and its Applications 1813Didier Gigmes and Sylvain R. A. Marque62 Atom Transfer Radical Polymerization (ATRP) and Addition (ATRA) and Applications 1851Tomislav Pintauer and Krzysztof Matyjaszewski63 Reversible Addition Fragmentation Chain Transfer (RAFT) Polymerization: Mechanism, Process and Applications 1895Christopher Barner-Kowollik, James P. Blinco, Mathias Destarac, Kristofer J. Thurecht and S´ebastien Perrier64 Sb, Bi, Te, and I-Transfer Polymerization and Applications 1931Shigeru Yamago and Eiichi Kayahara65 Spin Labels and Spin Probes 1965David Bardelang, Mica¨el Hardy, Olivier Ouari and Paul Tordo66 Radical Thiol–X Click Chemistry 2017Niels ten Brummelhuis and Helmut Schlaad67 Conducting Polymers: Applications in Electronics and Photovoltaics 2057Huanli Dong and Wenping Hu68 Silicon Radical Surface Chemistry 2081Bart Rijksen, Mabel A. Caipa Campos, Jos M. J. Paulusse and Han Zuilhof69 Persistent and Stable Silyl Radicals 2117Boris Tumanskii, Miriam Karni and Yitzhak Apeloig70 Physical Properties of Thiazyl Radicals Toward Conductive and Magnetic Materials 2147Kunio Awaga71 Polyradicals in Batteries 2163Kenichi Oyaizu and Hiroyuki Nishide72 Radical Chemistry on Fullerenes 2171Manolis D. Tzirakis and Michael Orfanopoulos73 A Paradigm for the Radical-Mediated Photochemical Synthesis of Metal Nanostructures 2197Juan C. Scaiano, Kevin G. Stamplecoskie, Katherine L. McGilvray and Natalia L. PacioniAuthor Index 2211Subject Index