LANDOLT-BÖRNSTEIN. Zahlenwerte und Funktionen aus Naturwissenschaften und Technik. Neue Serie. Gesamtherausgabe: O. Madelung

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1 LANDOLT-BÖRNSTEIN Zahlenwerte und Funktionen aus Naturwissenschaften und Technik Neue Serie Gesamtherausgabe: O. Madelung Gruppe II: Atom- und Molekularphysik Band 17 Ergänzung und Erweiterung zu Band 9 Magnetische Eigenschaften freier Radikale Teilband c Konjugierte Kohlenstoff- und Stickstoff-Radikale A. Berndt E A. Neugebauer Herausgeber: H. Fischer Springer-Verlag Berlin Heidelberg New York London Paris Tokyo

2 Magnetic properties of free radicals Subvolume c: Conjugated carbon-centered and nitrogen radicals General introduction H. FISCHER, Physikalisch-Chemisches Institut der Universität Zürich, Switzerland A Definition and substances 1 B Magnetic properties 1 C Arrangements of the tables 3 D Monographs 3 4 Carbon radicals with conjugated rc-systems A. BERNDT, Fachbereich Chemie der Universität Marburg, Germany '4.1 Introduction Radicals with 3 conjugated 7i-electrons Allyl and deuterated allyl radicals Alkyl-substituted allyl radicals Allyl radicals containing Cl Allyl radicals containing oxygen Oxygen in a-position Oxygen in/?-, y... position Allyl radicals containing sulfur Allyl radicals containing nitrogen or phosphorus Allyl radicals containing Silicon Allyl radicals containing Ag, AI, Au, Cu Phenyl- and aryl-substituted allyl radicals Aza-allyl and 2-oxaallyl radicals Semicyclic allyl radicals Cyclopropenyl radicals Isocyclic allyl radicals (cyclobutenyl, cyclopentenyl,...) Heterocyclic allyl radicals membered rings containing oxygen membered rings containing sulfur membered rings containing two heteroatoms membered rings containing oxygen membered rings containing nitrogen Bicyclic allyl radicals Allenyl (propargyl) radicals Radicals with 5 conjugated 7i-electrons Pentadienyl radicals Pentenynyl radicals Pentadiynyl radicals Semicyclic pentadienyl radicals Cyclic pentadienyl radicals Cyclopentadienyl radicals 70

3 VII Cyclopentadienyl and deuterated cyclopentadienyl radicals Alkyl-substituted cyclopentadienyl radicals Cyclopentadienyl radicals containing fluorine Cyclopentadienyl radicals containing oxygen Cyclopentadienyl radicals containing Silicon Cyclopentadienyl radicals containing germanium or tin Aryl-substituted cyclopentadienyl radicals Cyclohexadienyl radicals Cyclohexadienyl radicals without substituents at C(l) Cyclohexadienyl radicals with one substituents at C(l) Cyclohexadienyl radicals with two substituents at C(l) Aza-cyclohexadienyl radicals ,5-Diaza-cyclohexadienyl radicals Pyryl radicals Pyryl radicals without aryl rings directly bound to the pyryl ring Pyryl radicals with isocyclic aryl rings directly bound to the pyryl ring Pyryl radicals with heterocyclic aryl rings directly bound to the pyryl ring Thiapyryl radicals Thiapyryl radicals without aryl rings directly bound to the thiapyryl ring Thiapyryl radicals with isocyclic aryl rings directly bound to the thiapyryl ring Thiapyryl radicals with heterocyclic aryl rings directly bound to the thiapyryl ring Pyridinyl radicals //-Pyridinyl radicals Methyl-pyridinyl radicals Ethyl-, 1-propyl-, 1-butyl- and 1 -benzyl-pyridinyl radicals l-bis(alkoxycarbonyl)methylide pyridinyl radicals Trimethylsilyl- and 1-triphenylsilyl-pyridinyl radicals Trimethylgermyl- and 1-triphenylgermyl-pyridinyl radicals Trialkyl-stannyl-pyridinyl radicals Dialkylboryl-pyridinyl radicals Aza-pyridinyl radicals Phosphorinyl radicals Phosphorinyl radicals with one exocyclic bond at phosphorus Phosphorinyl radicals with two exocyclic bonds and a positive Charge at phosphorus Phosphorinyl radicals with three exocyclic bonds at phosphorus " Sila-cyclohexadienyl radicals Radicals with 7 conjugated 7r-electrons Heptatrienyl radicals Trivinylmethyl radicals Heptadienynyl radicals Cycloheptatrienyl radicals Cyclopentadienidemethyl radicals Benzyl radicals Benzyl radicals without substituents at the exocyclic carbon atom C (7) Benzyl radicals with one substituent at C(7) Benzyl radicals with two substituents at C(7) ,7-Dialkyl-benzyl radicals Methylene-benzyl radicals Benzyl radicals with halogen containing substituents at C(7) Benzyl radicals with oxygen and oxygen containing substituents at C(7) Benzyl radicals with one a-oxygen atom at C(7) Benzyl radicals with two a-oxygen atoms at C(7) Benzyl radicals with oxygen in ß-position relative to C(7) Benzyl radicals with sulfur and sulfur containing substituents at C(7) Benzyl radicals with nitrogen containing substituents at C(7) Benzyl radicals with phosphorus containing substituents at C(7) Benzyl radicals with selenium containing substituents at C(7)

4 VIII Benzyl radicals with Silicon containing substituents at C(7) Benzyl radicals with germanium containing substituents at C(7) Benzyl radicals with tin containing substituents at C(7) Benzyl radicals with boron containing substituents at C(7) Benzyl-type radicals containing heterocyclic 67c-electron ring Systems Furylmethyl radicals Furylmethyl radicals Furylmethyl radicals Thenyl (thienylmethyl) radicals Thenyl radicals Thenyl radicals Selenophenylmethyl radicals Azabenzyl radicals Bicyclic benzyl-type radicals Bicyclic benzyl-type radicals derived from indanone and thioindanone Bicyclic benzyl-type radicals derived from indole Tetralin-1-yl radical Bicyclic benzyl-type radicals derived from chromanone and thiachromanone Radicals with 9 conjugated re-electrons Indenyl radical a-hydronaphthyl and related radicals Benzopyryl radicals Benzothiapyryl radicals Benzopyridinyl (quinolinyl, isoquinolinyl) radicals Hydroindolyl radicals ß-Hydronaphthyl radicals Radicals with 11 conjugated 7r-electrons Radicals with 13 conjugated K-electrons Phenalenyl (perinaphthenyl) radicals Diphenylmethyl radicals Diphenylmethyl radicals without substituents at the central carbon atom C(7) Diphenylmethyl radicals with substituents at C(7) Alkyldiphenylmethyl radicals (including 7-benzyl- and 7-triphenylmethyl-diphenylmethyl) Diphenylmethyl radicals with halogen and halogen containing substituents at C(7) Diphenylmethyl radicals with oxygen and oxygen containing substituents at C(7) Diphenylmethyl radicals with sulfur and sulfur or selenium containing substituents at C(7) Diphenylmethyl radicals with nitrogen containing substituents at C(7) Diphenylmethyl radicals with phosphorus containing substituents at C(7) Diphenylmethyl radicals with Silicon containing substituents at C(7) Diphenylmethyl radicals with germanium and tin containing substituents at C(7) Diphenylmethyl radicals with Pb, B and Cr containing substituents at C(7) Diphenylmethyl-type radicals related to phenylindanyl Fluorenyl radicals Fluorenyl radicals without substituents at C(9) Fluorenyl radicals with alkyl and arylalkyl substituents at C(9) Chlorofluorenyl radicals Hydroxyfluorenyl radicals and anion radicals from fluorenone and derivatives Fluorenyl radicals with oxygen in /J-position relative to C(9) Fluorenyl radicals with sulfur containing substituents at C(9) Fluorenyl radicals with nitrogen and phosphorus containing substituents at C(9) Fluorenyl radicals with substituents containing Si, Ge and Sn at C(9) 315

5 IX Dibenzocyclohexadienyl and related radicals Xanthyl radicals Thioxanthyl and related radicals Selenoxanthyl radicals Acridinyl and related radicals Phenanthridinyl and related radicals Diphenylmethyl-type radicals containing heterocyclic 67i-electron Systems Diphenylmethyl-type radicals containing furan rings Diphenylmethyl-type radicals containing thiophene and related rings Diphenylmethyl-type radicals containing thiazol rings Diphenylmethyl-type radicals containing Pyridine rings Radicals with 15 conjugated 7t-electrons Radicals with 17 conjugated re-electrons Radicals with 19 conjugated 7t-electrons Benzopyrenyl radical Triphenylmethyl radicals Phenylfluorenyl radicals Triphenylmethyl radicals with carbon-connected or(ao-positions Phenylxanthyl radicals Triphenylmethyl-type radicals containing 5-membered rings Figures References for Nitrogen-centered radicals F. A. NEUGEBAUER, Max-Planck-Institut für medizinische Forschung, Abteilung Organische Chemie, Jahnstr. 29, D-6900 Heidelberg, West Germany 5.0 Introduction Aminyl radicals: R-N-R (R=H, C) Acyclic aminyl radicals Alkylaminyls Vinylaminyls of type R'-N-CH=CHNR 2 R 3 : Arylaminyls 397 O I Acylaminyls: R'-C-N-R Cyclic aminyl radicals Monocyclic aminyls Aminyls from three-membered rings Aminyls from four-membered rings Aminyls from five-membered rings Aminyls from six-membered rings Fused polycyclic aminyls Based on five-membered ring Based on six-membered ring Borylaminyl radicals: -N-B^ 438 I. I 5.3 Germylaminyl radicals: Ge N Ge 439

6 X 5.4 Hydrazyl and hydrazonyl radicals: N N^, N N= Acyclic hydrazyl radicals: R'-N-NR^ Leading atom of R 1, R 2, and R 3 : Hydrogen or carbon Alkylhydrazyls Arylhydrazyls Cyano-, acyl-, and thioacylhydrazyls Leading atom ofr 1 and R 3 : Hydrogen or carbon Leading atom of R 2 and R 3 : Hydrogen or carbon Leading atom R 1, R 2, and R 3 : Other than carbon Cyclic hydrazyl radicals: N-N / Monocyclic hydrazyls Hydrazyls from three-membered rings Hydrazyls from four-membered rings Hydrazyls from five-membered rings Hydrazyls from six-membered rings Fused polycyclic hydrazyls Acyclic and cyclic hydrazonyl radicals: N N= Oxyaminyl radicals: N O Acyclic oxyaminyl radicals: R'-N-OR Leading atom of R 1 and R 2 : Carbon Leading atom ofr 1 : Carbon Leading atom of R 2 : Carbon Leading atom ofr 1 and R 2 : Other than carbon Cyclic oxyaminyl radicals: N O Phosphorylaminyl radicals: R-N-P(0)R O O Thioaminyl radicals: -N-S-, -N-S-, -N-S-, -N-S NR Acyclic thioaminyl radicals Sulfenamidyl radicals: R'-N-S-R Leading atom ofr 1 : Carbon Leading atom of R : Other than carbon 517 O Sulfinamidyl radicals: R-N-S-R 522 / \ I " Sulfonamidyl radicals: R-N-S0 2 -R R-N-S-R 525 \ NR / Cyclic thioaminyl radicals Monocyclic thioaminyls Thioaminyls from four-membered rings Thioaminyls from five-membered rings Thioaminyls from six-membered rings Fused polycyclic thioaminyls Bridged thioaminyls Silylaminyl radicals: R-N-SiR Iminyl radicals: ^C=N' Iminyls of type RCH=N Iminyls of type R 1 R 2 C=N' Diazenyl radicals: R-'N + =N~ 575

7 XI 5.11 Triazenyl radicals: R-N"-N + =N-R Iminoxyl radicals: ^C=N-0" Acyclic iminoxyl radicals Iminoxyls of type RCH=N-CT Iminoxyls of type R 1 R 2 C=N-0' Leading atom of R 1 and R 2 : Carbon Leading atom of R 1 or R 2 : Other than carbon Leading atom of R 1 and R 2 : Other than carbon Cyclic iminoxyl radicals: fc=n-0" Monocyclic iminoxyls Fused polycyclic iminoxyls (Azo)oxyl radicals of Type R 2 N=N-0" Iminothiyl radicals: ^C=N-S' References for List of Symbols and abbreviations 643