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Can Four‐Membered Heterophosphete Structures Exist? The Contribution of Phosphorus d Orbitals to Antiaromaticity
Author(s) -
Mucsi Zoltán,
Kötvélyesi Tamás,
Viskolcz Béla,
Csizmadia Imre G.,
Novák Tibor,
Keglevich György
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600916
Subject(s) - antiaromaticity , chemistry , heteroatom , ring (chemistry) , atomic orbital , phosphorus , aromaticity , atom (system on chip) , computational chemistry , molecular orbital , stereochemistry , electron , organic chemistry , molecule , physics , quantum mechanics , computer science , embedded system
The large instability of heterophosphete compounds, composed of a four‐membered unsaturated ring with a pentavalent phosphorus atom and a heteroatom, has been identified and characterised by first‐principle molecular orbital computations, at several levels of theory. It has been shown that strong electron‐withdrawing groups bound to the phosphorus atom are able to stabilize the system. The extent of antiaromaticity of these compounds is examined and quantified by a linear aromatic and antiaromatic scale.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)