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Low‐Valent Silicon in Formally Antiaromatic Four‐Membered Ring Systems
Author(s) -
Jutzi Peter
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201103254
Subject(s) - antiaromaticity , silicon , ring (chemistry) , lone pair , atomic orbital , nitrogen , characterization (materials science) , crystallography , resonance (particle physics) , chemistry , materials science , computational chemistry , atomic physics , nanotechnology , aromaticity , molecule , physics , organic chemistry , quantum mechanics , electron
The fundamental question of how silicon handles antiaromaticity in four‐membered ring systems has been answered by the synthesis and characterization of the first tetrasilacyclobutadiene Si 4 Ar 4 ( 1 ) and by the first dimeric silaisonitrile Si 2 (NAr′) 2 ( 2 ). Compound 1 is best described by the charge‐separated resonance structure 1′ and 2 by a structure with π‐type lone pairs at the nitrogen atoms and vacant π orbitals at the silicon atoms.