Arsole Aromaticity Revisited
Lett. Org. Chem.
2 (2005) 469–474.
Mikael P. Johansson,
Department of Chemistry, Laboratory for Instruction in Swedish,
P.O. Box 55, University of Helsinki, FI-00014 Helsinki, Finland
The aromaticity of arsoles has been debated in the literature for
years. Some measures indicate arsole to be non-aromatic, others
attribute at least slight aromaticity to the molecule. Here, we
take a ring-current view of aromaticity, and study arsole in more
detail. We make comparisons to the nitrogen analogue pyrrole, the
phosphorous analogue phosphole, and the carbon analogue
cyclopentadiene. The newly developed gauge-including magnetically
induced currents (GIMIC) method provides a direct measure of the
current flow in molecules. Using GIMIC, we show that arsole
indeed is almost half as aromatic as pyrrole. Phosphole comes in
between. Even cyclopentadiene is found to possess a moderately
strong induced ring current, thus questioning the accepted
classification of this molecule as a non-aromatic reference system.
Full text (Ingenta web)
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