Landolt-Brnstein GROUP II
: Molecules and Radicals VOLUME 26 
Magnetic Properties of Free Radicals SUBVOLUME C Nitrogen and Oxygen Centered Radicals 
Title Pages, Contributors, Preface, Table of Contents 
 Title Pages 
 Contributors
 Preface 
Table of Contents

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 7 

9 
Nitrogen-centered monoradicals, biradicals and high-spin nitrenes (F.A. NEUGEBAUER) 7 

9.1 
Introduction 7 

9.1.1 
General remarks 7 

9.1.2 
Arrangement of tables 8 

9.1.3 
Abbreviations 9 

9.2 
Aminyl radicals of type RNR (R = H, C) 10 

9.2.1 
Acyclic aminyl radicals 10 

9.2.1.1 
Alkylaminyl radicals 10 

9.2.1.2 
Vinylaminyl radicals 13 

9.2.1.3 
Arylaminyls 14 

9.2.1.4 
Aminyl radicals with heterocyclic substituent 17

9.2.1.5 
Cyano- and acylaminyl radicals 21 

9.2.2 
Cyclic aminyl radicals 22 

9.2.2.1 
Monocyclic aminyl radicals 22 

9.2.2.1.1 
Aminyl radicals from four-membered rings 22 

9.2.2.1.2 
Aminyl radicals from five-membered rings 22 

9.2.2.1.3 
Aminyl radicals from six-membered rings 25 

9.2.2.2 
Fused polycyclic aminyl radicals 33 

9.2.2.2.1 
Based on five-membered rings 33 

9.2.2.2.2 
Based on six-membered rings 39 

9.2.2.2.3 
Based on seven-membered rings 66 

9.3 
Germylaminyl radicals of type RNGeR3 67 

9.4 
Hydrazyl and hydrazonyl radicals: R1NNR2R3, R1NN=CR2R3 68 

9.4.1 
Acyclic hydrazyl radicals 68 

9.4.1.1 
Leading atom of R1, R2, and R3: Hydrogen or carbon 68 

9.4.1.1.1 
Alkylhydrazyl radicals 68 

9.4.1.1.2 
Arylhydrazyl radicals 69 

9.4.1.1.3 
Cyano- and acylhydrazyl radicals 71 

9.4.1.2 
Leading atom of R1: Other than hydrogen or carbon 74 

9.4.1.3 
Leading atom of R2: Other than hydrogen or carbon 76 

9.4.1.4 
Leading atom of R1 and R2: Other than hydrogen or carbon 76 

9.4.2 
Cyclic hydrazyl radicals 77 

9.4.2.1 
Monocyclic hydrazyl radicals 77 

9.4.2.1.1 
Hydrazyl radicals from three-membered rings 77 

9.4.2.1.2 
Hydrazyl radicals from five-membered rings 78 

9.4.2.1.3 
Hydrazyl radicals from six-membered rings 90 

9.4.2.2 
Fused polycyclic hydrazyl radicals 101 

9.4.3 
Acyclic and cyclic hydrazonyl radicals 106 

9.4.3.1 
Acyclic hydrazonyl radicals 106 

9.4.3.2 
Cyclic hydrazonyl radicals 110 

9.5 
Oxyaminyl radicals: NO 111 

9.5.1 
Acyclic oxyaminyl radicals: R1NOR2 111 

9.5.1.1 
Leading atom of R1 and R2: Carbon 111 

9.5.1.2 
Leading atom of R2: Other than carbon 134 

9.5.1.3 
Leading atom of R1: Other than carbon 139 

9.5.2 
Cyclic oxyaminyl radicals 140 

9.6 
Thioaminyl radicals: NS, NS(=O), NSO2 142 

9.6.1 
Acyclic thioaminyl radicals 142 

9.6.1.1 
Sulfenamidyl radicals: R1NSR2 142 

9.6.1.1.1 
Leading atom of R1 and R2: Carbon 142 

9.6.1.1.2 
Leading atom of R1: Other than carbon 163 

9.6.1.2 
Sulfinamidyl radicals: R1NS(=O)R2 165 

9.6.1.3 
Sulfonamidyl radicals: R1NSO2R2 165 

9.6.2 
Cyclic thioaminyl radicals 166 

9.6.2.1 
Monocyclic thioaminyl radicals 166 

9.6.2.1.1 
Thioaminyl radicals from five-membered rings 166 

9.6.2.1.2 
Thioaminyl radicals from six-membered rings 182 

9.6.2.1.3 
Thioaminyl radicals from eight-membered rings 184 

9.6.2.2 
Fused polycyclic thioaminyl radicals 185 

9.6.2.3 
Bridged thioaminyl radicals 195 

9.7 
Selenoaminyl radicals: NSe 199 

9.8 
Iminyl radicals: >C=N 201 

9.8.1 
Iminyl radicals of type RCH=N201 

9.8.2 
Iminyl radicals of type R1R2C=N 204 

9.9 
Diazenyl radicals: RN+=N-209 

9.10 
Iminoxyl radicals: >C=NO 211 

9.10.1 
Acyclic iminoxyl radicals 211 

9.10.1.1 
Iminoxyl radicals of type RCH=NO, leading atom of R: Carbon 211 

9.10.1.2 
Iminoxyl radicals of type R1R2C=NO217 

9.10.1.2.1 
Leading atom of R1 and R2: Carbon 217 

9.10.1.2.2 
Leading atom of R2: Other than carbon 224 

9.10.1.2.3 
Leading atom of R1 and R2: Other than carbon 241 

9.10.2 
Cyclic iminoxyl radicals 241 

9.10.2.1 
Monocyclic iminoxyl radicals 241 

245 
248 
250 
250 
250 
250 
251 
252 
252 
253 
255 
256 
256 
257 
258 
259 
259 
259 
262 
262 
262 
280 
287 
288 
288 
289 
290 

291 
291 
291 
291 
292 
292 
293 
296 
296 
297 

Bis(arylnitrenes) linked by -HC=CH-, -[C=C]n-, -(1,3-C6H4)-,.or -C=C-(1,3-299 
C6H4)-C=C-
Bis(arylnitrenes) linked by carbocyclic or heterocyclic bridges 302 

Bis(arylnitrenes) linked by -CONH- 303 

Bis(arylnitrenes) linked by hetero atoms: O, S, Si 304 

Heterocyclic dinitrenes
Polynitrenes (S = 3) 
References for 9 
Review articles
References for 9.29.12 

305 
307 
309 
309 
309 




10 
Oxy- and peroxyalkyl radicals (J.A. HOWARD) 323 

10.1 
Introduction 323 

10.2 
Carbonyloxy radicals 323 

10.3 
Sulfinyl radicals 326 

10.4 
Alkylperoxy radicals 328 

10.5 
Alkenylperoxy radicals 330 

10.6 
Substituted alkylperoxy radicals 331 

10.7 
Aromatic peroxy radicals 335 

10.8 
Thiylperoxy radicals 335 

10.9 
Sulphonylperoxyl radicals 337 

10.10 
Peroxyl radicals from biological molecules 337 

10.11 
Polymer peroxyl radical 338 

10.12 
Metal centered peroxyl radical 339 

10.13 
References for 10 340 

11 
Aroxyl radicals (R. MECKE, H.H. JGER, M. JGER) 341 

11.1 
Introduction 341 

11.1.1 
General remarks 341 

11.1.2 
Arrangement of the tables 341 

11.1.3 
Abbreviations 342 

11.2 
Carbocycles 343 

11.2.1 
Monocyclic compounds 343 

11.2.1.1 
Phenoxyls 343 

11.2.1.1.1 
Phenoxyl 343 

11.2.1.1.2 
Monosubstituted phenoxyls 343 

11.2.1.1.2.1 
Tyrosyl 353 

11.2.1.1.2.2 
Tyrosine derived radicals 354 

11.2.1.1.2.3 
Tyrosine radicals in biological systems 354 

11.2.1.1.3 
Disubstituted phenoxyls 373 

11.2.1.1.4 
Trisubstituted phenoxyls 383 

11.2.1.1.4.1 
2,3,4-trisubstituted phenoxyls 383 

11.2.1.1.4.2 
2,3,5-trisubstituted phenoxyls 383 

11.2.1.1.4.3 
2,3,6-trisubstituted phenoxyls 384 

11.2.1.1.4.4 
2,4,5-trisubstituted phenoxyls 387 

11.2.1.1.4.5 
2,4,6-trisubstituted phenoxyls (1/6) 387 

11.2.1.1.4.5 
2,4,6-trisubstituted phenoxyls (2/6) 398 

11.2.1.1.4.5 
2,4,6-trisubstituted phenoxyls (3/6) 409 

11.2.1.1.4.5 
2,4,6-trisubstituted phenoxyls (4/6) 423 

11.2.1.1.4.5 
2,4,6-trisubstituted phenoxyls (5/6) 439 

11.2.1.1.4.5 
2,4,6-trisubstituted phenoxyls (6/6) 459 

11.2.1.1.4.6 
3,4,5-trisubstituted phenoxyls 474 

11.2.1.1.5 
Tetrasubstituted phenoxyls 475 

11.2.1.1.6 
Pentasubstituted phenoxyls 479 

11.2.2 
Condensed ring systems 481 

11.2.2.1 
Systems with condensed non-aromatic rings 481 

11.2.2.2 
Naphthoxyls 481 

11.2.2.3 
Anthroxyls 482 

11.2.2.4 
Polycondensed systems 483 

11.3 
Heterocycles 486 

11.3.1 
N-heterocycles 486 

11.3.2 
O-heterocycles 487 

11.3.2.1 
5-membered heterocyclic systems 487 

11.3.2.2 
6-membered heterocyclic systems 488 

11.3.2.3 
Condensed dioxol systems 494 

11.3.3 
S-heterocycles 496 

11.4 
Cations 499 

11.5 
Bi- and polyradicals 513 

11.6 
References for 11 524 

III General symbols and abbreviations (H. FISCHER) 533 

A Symbols 533 

B Abbreviations 533 

C Substances or part of substances 534 



9.10.2.2 
9.10.2.3 
9.11 
9.11.1 
9.11.2 
9.11.2.1 
9.11.2.2 
9.11.3 
9.11.3.1 
9.11.3.2 
9.11.4 
9.11.5 
9.11.5.1 
9.11.5.2 
9.11.5.3 
9.12 
9.12.1 
9.12.1.1 
9.12.1.2 
9.12.1.3 
9.12.1.4 
9.12.1.5 
9.12.1.6 
9.12.1.7 
9.12.1.8 
9.12.1.9 
9.12.1.10 
9.12.2 
9.12.2.1 
9.12.2.2 
9.12.2.3 
9.12.2.4 
9.12.2.5 
9.12.2.6 
9.12.3 
9.12.4 
9.12.4.1 
9.12.4.2 
9.12.4.3 
9.12.4.4 
9.12.4.5 
9.12.4.6 
9.12.4.7 
9.12.5 
9.13 
9.13.1 
9.13.2 
Fused polycyclic iminoxyl radicals
Bridged iminoxyl radicals
Nitrogen-centered biradicals 
Aminyl biradicals
Hydrazyl biradicals
Acyclic hydrazyl biradicals
Cyclic hydrazyl biradicals
Thioaminyl biradicals
Acyclic thioaminyl biradicals
Cyclic thioaminyl biradicals
Cyclic selenoaminyl biradical
Biradicals with different kinds of radical centers
Type R1NCR2R3
Type R1NN(O)R2 
Type R1NO
High-spin mono- and polynitrenes
Mononitrenes
Alkyl nitrenes
Cyano nitrene 
Carbonyl nitrene 
Aryl nitrenes
Heterocyclic nitrenes
Boryl nitrene 
Phosphoryl nitrene 
Sulfonyl nitrenes
Silyl nitrenes
Stannyl nitrene 

Mononitrenes and additional radicals (S = 3/2, S = 2) 
Nitrene and benzyl
Nitrene and aminyl
Nitrene and hydrazyl
Nitrene and nitroxyde 
Nitrene, alkyl and aminyl
Nitrene and carbine
Quinonoidal dinitrenes (iminyl biradicals)
Dinitrenes (S = 2) 
Arylene dinitrenes
Bis(arylnitrenes) linked by >C=CH2 or >C=O

