Table of contents Magnetic Properties of Free Radicals Subvolume E: Phosphorus-Centered Radicals, Radicals Centered on Other Heteroatoms, Organic Radical Ions Part 1 I Introduction 
I General introduction [H.Fischer]............................. 1A Definition and substances................................. 1B Magneticproperties.................................... 1C Arrangements of the tables................................ 3D Monographs, reviews and important conference proceedings .............. 4
II Data 
13 	Phosphorus-centered organic radicals and related radical ions 
[S.R.A.Marque, P.Tordo]................................ 7

13.1Introduction........................................ 7
13.1.1Generalremarks...................................... 7
13.1.2Formulae and structure.................................. 7
13.1.3Reviews.......................................... 8
13.1.4Remarks.......................................... 8

13.2 Phosphinyl radicals X2Pand related species....................... 9
13.3 Phosphonyl(X2P =O) and thiophosphonyl (X2P =S) radicals.............. 22

13.4 Phosphoranyl radicals X4P , including related species.................. 29

13.5 Phosphoniumyl cation radicals X3P +, phosphine dimer cation radicals X3P P+X3, phosphate anion radicals, and related species....................... 52 
13.6Miscellaneous....................................... 63
13.7References for 13..................................... 79
13.7.1Reviewarticles...................................... 79
13.7.2References for 13.2 to 13.6................................ 79
14	Radicals centered on other heteroatoms [R.F.C.Claridge]................ 83

14.1Introduction........................................ 83
14.2Sulfur-, selenium-, tellurium-centered radicals...................... 84
14.2.1 	Thiyl radicals of the type RS , R-S R, R-S -R2...................... 84

14.2.2 	Sulfinyl radicals of the typeR-S =O........................... 87

14.2.3 	Sulfonyl radicals of the typeRS O2............................ 89
VIII Table of contents 
14.2.4 Sulfuranyl radicals of the type X-S -R2, X2S -R, S X3, S X4 .............. 92

14.2.5 Disulfide radicals of the type R-S-S ........................... 93
14.2.6 Cationradicals ...................................... 94

14.2.6.1 Cation radicals of the type R2S +, RPS +(incl.Se, Te).................. 94

14.2.6.2 Cation radicals of the type RS-SR +............................ 96

14.2.6.3 Cation radicals of the type R2S-O +, R2S-O2 +, and R-S +-N-R.............. 98

14.2.7 Anionradicals...................................... 100 

  
14.2.7.1 Anion radicals of the type R=S, RSH2 , R3S (incl.Se, Te)............. 100 
 
14.2.7.2 Anion radicals of the type RS-SR ........................... 106 

  
14.2.7.3 Anion radicals of the type RS-X, RS-O, RS-O2 (incl.Se, Te)........... 109 
14.3 Silicon-centered radicals and related radical ions ................... 111 


14.3.1 Silyl radicals X3Si ................................... 111 
14.3.2 Silyl radicals frompolysilanes............................. 119 

14.3.3 Silicon-centered anion radicals............................. 121 

14.3.4 Silicon-centered anion radicals frompolysilanes.................... 122 

14.3.5 Silicon-centered cation radicals............................. 123 

14.4 Germanium-centered radicals and related radical ions................. 129 


14.4.1 Germyl radicals X3Ge ................................. 129 
14.4.2 Germanium-centered anion radicals .......................... 130 

14.4.3 Germanium-centered cation radicals.......................... 131 

14.5 Tin-centered radicals and related radical ions...................... 132 


14.5.1 Stannyl radicals X3Sn ................................. 132 
14.5.2 Tin-centered anion radicals............................... 133 

14.5.3 Tin-centered cation radicals............................... 134 

14.6 Boron-centered radicals and related radical ions.................... 135 


14.6.1 Boryl radicals X3B................................... 135 
14.6.2 Boron-centered anion radicals ............................. 138 

14.6.3 Boron-centered cation radicals............................. 138 

14.7 Aluminum-centered radicals and related radical ions ................. 139 

14.7.1 Aluminum-centered neutral radicals .......................... 139 

14.7.2 Aluminum-centered anion radicals........................... 145 

14.8 Gallium-centered radicals and related radical ions................... 146 

14.8.1 Gallium-centered neutral radicals............................ 146 

14.8.2 Gallium-centered radical anions ............................ 146 

14.9 Mercury-centered radicals and related radical ions................... 148 

14.9.1 Cationradicals ..................................... 148 

14.10 References for Chapter 14 ............................... 151 

15 Organic anion radicals with the exception of semiquinones 
[C.C.Rowlands, R.D.Farley].............................. 155 

15.1 Introduction....................................... 155 

15.1.1 Generalremarks..................................... 155 

15.1.2 Coverage........................................ 156 

15.1.3 Ordering......................................... 156 

15.1.4 Reviews and books................................... 156 

Table of contents IX 
15.2 Hydrocarbon and substituted hydrocarbon anion radicals ............... 157 

15.2.1 Hydrocarbon radical anions............................... 157 

15.2.2 Substitutedcompounds................................. 194 

15.2.2.1 Substituted radical anions................................ 194 

15.2.2.2 Perfluoro and perchloro substituted radical anions................... 207 

15.2.2.3 Substitutedfluorenones................................. 209 

15.3 Anion radicals fromheterocycles............................ 214 

15.3.1 Oxygen containing heterocycles ............................ 214 

15.3.1.1 Furan based heterocycles................................ 214 

15.3.1.1.1 Arylfurans........................................ 214 

15.3.1.1.2 Nitrofurans....................................... 215 

15.3.1.1.3 Arylbenzylfurans.................................... 216 

15.3.1.2 Bromonitrodioxanes .................................. 217 

15.3.1.3 Oxoporphycenes .................................... 218 

15.3.2 Nitrogen containing heterocycles............................ 219 

15.3.2.1 Halegenoimidazoles................................... 219 

15.3.2.2 Pyrazines and pyrazinophanes ............................. 220 

15.3.2.3 Phenanthroline and phenanthroline based platinumcomplexes............. 221 

15.3.2.4 Pyridine based heterocycles............................... 223 

15.3.2.4.1 Bipyridyls........................................ 223 

15.3.2.4.2 Dipyridylacetylenes................................... 223 

15.3.2.5 Porphycenes....................................... 224 

15.3.2.6 Pyrimidines....................................... 227 

15.3.2.7 Diphenylquinoxaline.................................. 227 

15.3.2.8 Boron substituted nitrogen containing heterocycles .................. 227 

15.3.2.9 Indolines ........................................ 231 

15.3.3 Sulphur containing heterocycles ............................ 233 

15.3.3.1 Thiophenes and polythiophenes............................. 233 

15.3.3.2 Dicyanomethylidenethiopyrans............................. 234 

15.3.3.3 Weitz type S-donors .................................. 235 

15.3.4 Phosphorus containing heterocycles .......................... 237 

15.3.5 Seleniumand telluriumcontaining heterocycles.................... 238 

15.3.6 Heterocycles with two or more different heteroatoms ................. 239 

15.4 Anion radicals fromnitro compounds.......................... 240 

15.5 Anion radicals fromcarbonyl compounds ....................... 254 

15.5.1 Esters and thioesters .................................. 254 

15.5.1.1 Arylesters........................................ 254 

15.5.1.2 Thioesters........................................ 263 

15.5.1.3 Oxocarbothioate and dithioate esters.......................... 264 

15.5.2 Aldehydes, ketones and their thio analogs....................... 269 

15.5.2.1 Aliphatic aldehydes and ketones............................ 269 

15.5.2.2 Furyl and thienyl aldehydes and ketones........................ 271 

15.5.2.3 Tropones........................................ 279 

15.5.2.4 Benzenedicarbaldehydes................................ 280 

15.5.2.5 Thiopyrane-2-thiones.................................. 281 

15.5.2.6 Silanones........................................ 282 

15.5.3 Semidiones....................................... 283 

15.5.3.1 Ethanediones...................................... 283 

15.5.3.2 Cyclobutanediones................................... 284 

15.5.3.3 But-2-ene-1,4-diones.................................. 285 

15.5.3.4 Thiadiazoloquinoxalinediones............................. 287 

X Table of contents 
15.5.3.5 Hypericin........................................ 288 

15.5.3.6 Dithioledithione..................................... 288 

15.5.3.7 Diones derived fromcarbohydrates........................... 289 

15.5.4 Acid anhydrides and derivatives............................ 290 

15.6 Anion radicals fromazo compounds.......................... 291 

15.6.1 Aliphaticazoalkenes.................................. 291 

15.6.1.1 Open chain azoalkenes................................. 291 

15.6.1.2 Cyclicazoalkenes.................................... 292 

15.6.1.3 Azopolycycloalkenes.................................. 299 

15.6.2 Benzo[c]cinnolines and azobenzene derivatives.................... 300 

15.6.2.1 Benzo[c]cinnolines................................... 300 

15.6.2.2 Azobenzenederivatives................................. 302 

15.6.3 Arylazophosphonates.................................. 302 

15.6.4 Bidiazines........................................ 303 

15.6.5 Tetrazines........................................ 306 

15.7 Other anion radicals................................... 309 

15.7.1 Sulphides and sulphones................................ 309 

15.7.1.1 Diphenylsulphides and sulphones............................ 309 

15.7.1.2 Aliphaticdisulphides.................................. 310 

15.7.2 Imines and imides.................................... 311 

15.7.2.1 Imines.......................................... 311 

15.7.2.2 Imides.......................................... 316 

15.7.3 Fullerenes........................................ 316 

15.7.4 Tetracyanoquinodimethanes .............................. 318 

15.7.5 Phenylcarbonitriles................................... 319 

15.7.6 Phosphaalkenes..................................... 320 

15.7.7 Silanes.......................................... 323 

15.8 References for 15.................................... 324 

III General symbols and abbreviations 
A Symbols......................................... 329 B Abbreviations...................................... 329 C Substances or part of substances............................ 330 
