Premium
Donor–Acceptor Adducts of a 1,3‐Disila‐2‐oxyallyl Zwitterion
Author(s) -
Cowley Michael J.,
Huch Volker,
Scheschkewitz David
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402750
Subject(s) - zwitterion , moiety , adduct , lewis acids and bases , chemistry , acceptor , delocalized electron , carbene , ionic bonding , natural bond orbital , medicinal chemistry , stereochemistry , crystallography , ion , molecule , computational chemistry , density functional theory , catalysis , organic chemistry , physics , condensed matter physics
In the presence of a Lewis acid or base, cyclotrisilene c Si 3 Tip 4 (Tip=2,4,6‐triisopropylphenyl) reacts with CO to form stable adducts of a 1,3‐disila‐2‐oxyallyl zwitterion. Coordination of an N‐heterocyclic carbene (NHC) to one silicon center results in a localized SiC bond, whereas B(C 6 F 5 ) 3 bonds to the carbonyl moiety leading to the delocalization of the positive charge over the oxyallyl moiety. Computational analysis of the electronic structure of the Lewis acid adduct reveals a considerable interaction between the two silicon atoms in 1,3‐position and thus aromaticity akin to the homocyclopropenium cation.