Table of contents 
Magnetic Properties of Free Radicals 

Subvolume D
: Nitroxide Radicals and Nitroxide Based High-Spin Systems 
I Introduction 
I 
General introduction [H. Fischer] ............................. 1

A 
Definition and substances ................................. 1

B
 Magnetic properties .................................... 1

C 
Arrangements of the tables................................ 3

D 
Monographs, reviews and important conference proceedings .............. 4

II Data 
12 
Nitroxide radicals and polynitroxides [A. Alberti] ................... 7

12.1 
Introduction ........................................ 7

12.1.1 
General remarks ...................................... 7

12.1.2 
Classifications ....................................... 7

12.1.3 
Abbreviations and acronyms............................... 8

12.1.4 
Summary table....................................... 9

12.2 
Acyclic nitroxides ..................................... 10

12.2.1 
Alkyl nitroxides ...................................... 10

12.2.2 
Dialkyl nitroxides ..................................... 12

12.2.2.1 
Methyl prim-alkyl nitroxides............................... 12

12.2.2.2 
Methyl sec-alkyl nitroxides ................................ 12

12.2.2.3 
Methyl tert-alkyl nitroxides ................................ 13

12.2.2.4 
Di-prim-alkyl nitroxides ................................. 14

12.2.2.5 
prim-Alkyl sec-alkyl nitroxides .............................. 16

12.2.2.6 
prim-Alkyl tert-alkyl nitroxides.............................. 19

12.2.2.6.1 
prim-Alkyl tert-butyl nitroxides.............................. 19

12.2.2.6.2 
prim-Alkyl tert-polyfluoroalkyl nitroxides ........................ 23

12.2.2.6.3 
prim-Alkyl other tert-alkyl nitroxides........................... 24

12.2.2.7 
Di-sec-alkyl nitroxides.................................. 24

12.2.2.8 
sec-Alkyl tert-alkyl nitroxides .............................. 27

12.2.2.8.1 
Acyclic sec-alkyl tert-butyl nitroxides [tBuN(O
)CH(XR1)R2 with X = Carbon] .... 27 
12.2.2.8.2 
Acyclic sec-alkyl tert-butyl nitroxides [tBuN(O
)CH(XR1)R2 with X = Nitrogen] . . . 81 
12.2.2.8.3 
Acyclic sec-alkyl tert-butyl nitroxides [tBuN(O
)CH(XR1)R2 with X = Oxygen] .... 86 
12.2.2.8.4 
Acyclic sec-alkyl tert-butyl nitroxides [tBuN(O
)CH(XR1)R2 with X = Halogen] .... 105 
12.2.2.8.5 

Acyclic sec-alkyl tert-butyl nitroxides [tBuN(O)CH(XR1)R2 with X = Phosphorus, Sulphur, Silicon] .........................106 

12.2.2.8.6 
Five-membered cyclic sec-alkyl tert-butyl nitroxides ..................109 

12.2.2.8.7 
Six-membered cyclic sec-alkyl tert-butyl nitroxides ................... 112 

12.2.2.8.8 
sec-Alkyl other tert-alkyl nitroxides ...........................124 

Table of contents	IX

12.2.2.9 	
Di-tert-alkyl nitroxides .................................. 137 

12.2.2.9.1 	
tert-Butyl acyclic-tert-alkyl nitroxides.......................... 137 

12.2.2.9.2 	
tert-Butyl cyclic tert-alkyl nitroxides ........................... 142 

12.2.2.9.3 	
Other di-tert-alkyl nitroxides............................... 146 

12.2.3	
Aryl nitroxides ......................................151 

12.2.4	
Aryl alkyl nitroxides ...................................154 

12.2.4.1	
Aryl methyl nitroxides ..................................154 

12.2.4.2 	
Aryl prim-alkyl nitroxides ................................155 

12.2.4.3 	
Aryl sec-alkyl nitroxides .................................167 

12.2.4.3.1 	
Aryl acyclic-sec-alkyl nitroxides [ArN(O)CH(XR1)R2 with X = Carbon]........ 167 

12.2.4.3.2 	
Aryl acyclic-sec-alkyl nitroxides [ArN(O)CH(XR1)R2 with X = Nitrogen] ....... 180 

12.2.4.3.3 	
Aryl acyclic-sec-alkyl nitroxides [ArN(O)CH(XR1)R2 with X = Oxygen] ....... 185 

12.2.4.3.4 	
Aryl acyclic-sec-alkyl nitroxides [ArN(O)CH(XR1)R2
with X = Phosphorus, Sulphur, Silicon] .........................186 

12.2.4.3.5 	
Aryl cyclic-sec-alkyl nitroxides .............................. 188 

12.2.4.4 	
Aryl tert-alkyl nitroxides ................................. 190 

12.2.4.4.1 	
Aryl tert-butyl nitroxides................................. 190 

12.2.4.4.2 	
Aryl other tert-alkyl nitroxides .............................. 197 

12.2.5	
Diaryl nitroxides......................................209 

12.2.6	
Heteroaryl alkyl nitroxides................................216 

12.2.7	
Heteroaryl aryl nitroxides .................................218 

12.2.8	
Acyl nitroxides......................................222 

12.2.8.1	
Acyl alkyl nitroxides and acyl aryl nitroxides ...................... 222 

12.2.8.2	
Benzoyl alkyl nitroxides .................................226 

12.2.8.3 	
2-(N-Methylpyrrolyl)carbonyl polyfluoroalkyl nitroxides ................ 228 

12.2.8.4 	
Aminocarbonyl, halocarbonyl, oxycarbonyl hydro, alkyl and aryl nitroxides ...... 237 

12.2.9	
Vinyl and iminyl nitroxides ................................238 

12.2.10	
Amino and nitroso nitroxides ...............................241 

12.2.10.1	
Alkyl amino nitroxides and alkyl nitroso nitroxides ................... 241 

12.2.10.2	
Aryl amino nitroxides and aryl nitroso nitroxides .................... 243 

12.2.11	
Azoxy nitroxides .....................................247 

12.2.12	
Oxynitroxides .......................................248 

12.2.12.1	
Hydroxynitroxides ....................................248 

12.2.12.2 	
Alkoxynitroxides .....................................248 

12.2.12.2.1 	
Alkoxy alkyl nitroxides ..................................248 

12.2.12.2.2 	
Alkoxy aryl nitroxides ..................................253 

12.2.12.3	
Boroxynitroxides.....................................256 

12.2.12.4 	
Silyloxy-, germyloxy- and phosphoxynitroxides ..................... 261 

12.2.13 	
Phosphonitroxides.....................................265 

12.2.14	
Silylnitroxides .......................................267 

12.2.15	
Thionitroxides .......................................268 

12.2.15.1	
Alkyl thionitroxides ....................................268 

12.2.15.2	
Aryl thionitroxides ....................................270 

12.2.15.3	
Dithionitroxides ......................................272 

12.3	
Cyclic nitroxides .....................................273 

12.3.1 	
Pyrrolidinyl-N-oxyls ...................................273 

12.3.1.1 	
Monosubstituted pyrrolidinyl-N-oxyls .......................... 273 

12.3.1.2	
2,2-Disubstituted pyrrolidinyl-N-oxyls .......................... 273 

12.3.1.3	
Trisubstituted pyrrolidinyl-N-oxyls ...........................276 

12.3.1.3.1	
2,2,3-Trisubstituted pyrrolidinyl-N-oxyls ........................276 

12.3.1.3.2	
2,2,4-Trisubstituted pyrrolidinyl-N-oxyl ......................... 277 

12.3.1.3.3 
2,2,5-Trisubstituted pyrrolidinyl-N-oxyl ......................... 278 

12.3.1.3.3.1 
5-XR-Substituted 2,2-dimethylpyrrolidine-N-oxyls  [X = Carbon] ...........278 

12.3.1.3.3.2 
5-XR-Substituted 2,2-dimethylpyrrolidine-N-oxyls [X = Nitrogen]........... 287 

12.3.1.3.3.3 
5-XR-Substituted 2,2-dimethylpyrrolidine-N-oxyls [X = Oxygen]........... 290 

12.3.1.3.3.4 
5-XR-Substituted 2,2-dimethylpyrrolidine-N-oxyls [X = Phosphorus] ......... 298 

12.3.1.3.3.5 
5-XR-Substituted 2,2-dimethylpyrrolidine-N-oxyls  [X = Sulphur]........... 298 

12.3.1.3.3.6 
5-Substituted 2-methyl,2-(dialkoxyphosphoryl)pyrrolidine-N-oxyls ........... 301 

12.3.1.3.3.7 
Other 2,2,5-trisubstituted pyrrolidine-N-oxyls ...................... 306 

12.3.1.4 
Tetrasubstituted pyrrolidine-N-oxyls ...........................320 

12.3.1.4.1 
3,5-Disubstituted 2,2-dimethylpyrrolidine-N-oxyls.................... 320 

12.3.1.4.2 
4,5-Disubstituted 2,2-dimethylpyrrolidine-N-oxyls.................... 321 

12.3.1.4.3 
5-Substituted 2,4-diphenyl-2-methylpyrrolidine-N-oxyls ................325 

12.3.1.4.4 
5,5-Disubstituted 2,2-dimethylpyrrolidine-N-oxyls.................... 328 

12.3.1.4.5 
Other 2,2,5,5-tetrasubstituted pyrrolidine-N-oxyls ....................343 

12.3.1.5 
Pentasubstituted pyrrolidine-N-oxyls ........................... 346 

12.3.1.5.1 
5-Substituted 2,2,4,4-tetramethylpyrrolidine-N-oxyls ..................346 

12.3.1.5.2 
3-Substituted 2,2,5,5-tetramethylpyrrolidine-N-oxyls ..................347 

12.3.1.5.3 
4-Substituted 2-(dialkoxyphosphoryl)-2,5,5-trimethylpyrrolidine-N-oxyls .......352 

12.3.1.5.4 
Other 2,2,4,5,5-pentasubstituted pyrrolidine-N-oxyls ..................354 

12.3.1.6 
Hexasubstituted pyrrolidine-N-oxyls ........................... 354 

12.3.1.6.1 
3,4-Disubstituted 2,2,5,5-tetramethylpyrrolidine-N-oxyls ................. 354 

12.3.1.6.2 
2,4,5-Trisubstituted 3,3,5-trimethylpyrrolidine-N-oxyls ................. 355 

12.3.1.6.3 
2,4-Disubstituted 3,5-di(spirocyclohexyl)pyrrolidine-N-oxyls .............. 357 

12.3.1.6.4 
2,2-Disubstituted 3,3,5,5-tetramethylpyrrolidine-N-oxyls ................. 357 

12.3.1.7 
Fused-ring pyrrolidine-N-oxyls .............................. 359 

12.3.2 
Pyrrolinyl-N-oxyls ....................................362 

12.3.2.1 
2-Pyrrolinyl-N-oxyls ...................................362 

12.3.2.2 
3-Pyrrolinyl-N-oxyls ...................................362 

12.3.3 
Pyrrolyl-N-oxyls...................................... 374 

12.3.4 
3-Pyrazolinyl-2-oxyls ...................................374 

12.3.5 
3-Imidazolidinyl-1-oxyls.................................375 

12.3.6 
2-Imidazolinyl-N-oxyls and 2-imidazolinyl-N-oxyls 3-oxide ..............382 

12.3.7 
3-Imidazolinyl-N-oxyls and 3-imidazolinyl-N-oxyls 3-oxide ..............397 

12.3.8 
3-Oxazolidinyl-N-oxyls .................................. 407 

12.3.9 
Piperidinyl-N-oxyls .................................... 415 

12.3.9.1 
6-Substituted 2,2-dimethylpiperidinyl-N-oxyls ...................... 415 

12.3.9.2 
2,6-Disubstituted 2,6-dimethylpiperidinyl-N-oxyls.................... 416 

12.3.9.3 
4-Substituted 2,2,6,6-tetramethylpiperidinyl-N-oxyls ..................417 

12.3.9.4 
4-Vinyl-2,2,6,6-tetramethylpiperidinyl-N-oxyls ..................... 434 

12.3.9.5 
4-Imino-2,2,6,6-tetramethylpiperidinyl-N-oxyls ..................... 435 

12.3.9.6 
4-Carbonyl-2,2,6,6-tetramethylpiperidinyl-N-oxyls ...................435 

12.3.9.7 
3,4-Disubstituted-2,2,6,6-tetramethylpiperidinyl-N-oxyls ................ 437 

12.3.9.8 
4,4-Disubstituted-2,2,6,6-tetramethylpiperidinyl-N-oxyls ................ 439 

12.3.9.9 
Decasubstituted piperidinyl-N-oxyls ........................... 442 

12.3.10 
Tetrahydropyridinyl-N-oxyls............................... 443 

12.3.11 
Tetrahydropyrazine-4-oxide-1-oxyls ...........................443 

12.3.12 
Phenoxazilinyl-N-oxyls and phenothiazilinyl-N-oxyls ..................445 

12.3.13 
Isoindolinyl-N-oxyls ...................................447 

12.3.14 
Indolinyl-N-oxyls, indolinonyl-N-oxyls and indoliminyl-N-oxyls ............452 

12.3.15 
Miscellaneous fused-rings nitroxides ...........................462 

12.3.16 
Polycyclic nitroxides...................................469 

12.3.17 
Cyclic and polycyclic acylnitroxides...........................471 

Table of contents XI

12.3.18 
Cyclic iminylnitroxides ..................................474 

12.3.19 
Other cyclic nitroxides ..................................474 

12.4 
Cyclic oxynitroxides ...................................476 

12.5 
Polynitroxides .......................................478 

12.5.1 
Bisnitroxides .......................................478 

12.5.1.1 
Bis(dialkylnitroxides)...................................478 

12.5.1.2 
Bis(alkyl-arylnitroxides) .................................478 

12.5.1.3 
Bis(alkyl-acylnitroxides).................................483 

12.5.1.4 
3-Imidazolidinyl bisnitroxides ..............................484 

12.5.1.5 
Bis(2,2,5,5-tetramethylpyrrolidinyl-N-oxyl) ....................... 485 

12.5.1.6 
Bis(2,2,5,5-tetramethylpyrrolinyl-N-oxyl) ........................ 485 

12.5.1.7 
Bis(3-imidazolinyl-N-oxyls) and bis(3-imidazolinyl-N-oxyls 3-oxide) ..........490 

12.5.1.8 
Bis(2,2,6,6-tetramethylpiperidinyl-N-oxyls) ....................... 500 

12.5.1.9 
Bicyclic bisnitroxides ...................................509 

12.5.1.10 
Other miscellaneous bisnitroxides ............................510 

12.5.2 
Trisnitroxides.......................................511 

12.5.3 
Other polynitroxides ...................................514 

12.6 
References for 12.....................................516 

12.6.1 
References for 12.1 ....................................516 

12.6.1.1 
References to some protein- and nucleic acid-derived nitroxides ............ 516 

12.6.1.2 
References to reviews on nitroxides, spin trapping and spin labeling .......... 516 

12.6.2 
References for 12.2 ....................................516 

12.6.3 
References for 12.3 and 12.4...............................525 

12.6.4 
References for 12.5 ....................................537 

III General symbols and abbreviations 
A
 Symbols ..........................................540 

B
 Abbreviations .......................................540 

C 
Substances or part of substances.............................541 




X Table of contents 
