ISSN:
0894-3230
Schlagwort(e):
Organic Chemistry
;
Physical Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
,
Physik
Notizen:
The structures of a series of heterosubstituted methylenecyclopropenes and methylenecyclopropanes were optimized at the HF/6-31G* level. All methylenecyclopropenes are planar except for the silicon analogue, which is bent at both C-3 and Si. The planar silicon structure is a transition state. The relative aromaticity of these compounds were evaluated using the C-1—C-3 bond length, the integrated charge on C-3 and the heteroatom, and delocalization energy. Second-row systems have slightly larger delocalization energies than their first-row counterparts, owing to their larger polarizability. Using these criteria, methylenecyclopropene and the silicon analogue are not aromatic and the N, O, P and S analogues are moderately aromatic. The planar silicon analogue is antiaromatic and bends from planarity to reduce this antiaromaticity.
Zusätzliches Material:
1 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/poc.610040407
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