D-ORBITAL EFFECTS IN SILICON-SUBSTITUTED PI-SYSTEMS .19. EFFECT OF R3SI AND R3SICH2 GROUPS ON ELECTRON STRUCTURE OF NITROBENZENE

被引:9
作者
ALT, H
BOCK, H
机构
[1] Institut für Anorganische Chemie, Universität München
关键词
D O I
10.1016/S0040-4020(01)83023-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electronic spectra, NO2-vibrational frequencies and half-wave reduction potentials of p-substituted nitrobenzenes O2NC6H4X (X = H, CH3, Si(CH3)3, CH2Si(CH3)3) were determined and interpreted by means of a localized orbital" model. The results prove for the neutral molecules increasing donor properties of the substituents in the order H < Si(CH3)3 < CH3 ≪ CH2Si(CH3)3. The Si ← Cπ-acceptor function into empty silicon atomic orbitals of the R3Si substituent is demonstrated especially in the enhanced stability of the p-trimethylsilyl-nitrobenzene radical anion. © 1969."
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页码:4825 / &
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共 29 条
[1]   BIRCH REDUCTIONS OF TRIMETHYLSILYL SUBSTITUTED AROMATIC COMPOUNDS CONTROLLED BY (SI]-CPI) INTERACTIONS [J].
ALT, H ;
FRANKE, ER ;
BOCK, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (07) :525-&
[2]   UV AND ESR STUDIES OF P-BIS(TRIMETHYLSILYL)- AND P-DIALKYLBENZENES [J].
ALT, H ;
BOCK, H ;
GERSON, F ;
HEINZER, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (11) :941-&
[3]  
ALT H, 1967, ANGEW CHEM, V79, P933
[4]  
ALT H, 1969, ANGEW CHEM, V81, P538
[5]   NITRATION OF ORGANOSILICON COMPOUNDS WITH COPPER NITRATE [J].
BENKESER, RA ;
BRUMFIELD, PE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (10) :4770-4773
[6]   ENERGY DIFFERENCES IN INNER MOLECULAR ORBITALS OF TERT-BUTYL AND TRIMETHYLSILYL PHENYL KETONES [J].
BOCK, H ;
ALT, H ;
SEIDL, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (11) :885-&
[7]   D-ORBITAL EFFECTS IN SILICON-SUBSTITUTED PI-ELECTRON SYSTEMS .10. VERTICAL IONIZING ENERGIES OF ALKYL- AND SILYLBENZENES [J].
BOCK, H ;
SEIDL, H ;
FOCHLER, M .
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (08) :2815-&
[8]   D-ORBITAL EFFECTS IN SILICON-SUBSTITUTED PI-ELECTRON SYSTEMS .15. COLOR OF SILYL KETONES [J].
BOCK, H ;
ALT, H ;
SEIDL, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (02) :355-&
[9]   D-ORBITAL EFFECTS IN SILICON SUBSTITUTED PI-ELECTRON SYSTEMS .12. SOME SPECTROSCOPIC PROPERTIES OF ALKYL AND SILYL ACETYLENES AND POLYACETYLENES [J].
BOCK, H ;
SEIDL, H .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1968, (10) :1158-&
[10]  
BOCK H, 1967, ANGEW CHEM INT EDIT, V6, P943