De-aromatizing Phosphole

Abstract : Quantum-chemical DFT calculations using the B3LYP functionals have been carried out for 1-Rsubstitued phospholes and some 1-R-substitued 3,4-dimethylphospholes where R ) H, Me, Ph, CN, OH, OMe, F, Cl, and Br. The aromaticity of the phospholyl rings is interpreted as a function of geometric, magnetic, and energetic indexes. It is shown, in agreement with previous experimental results, that phosphole aromaticity does not correlate with pyramidality at phosphorus. Variation of hyperconjugative and, to a lesser extent, conjugative effects is responsible for the change in cyclic delocalization for the phospholes studied here.
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Contributeur : Gilles Frison <>
Soumis le : jeudi 11 mars 2010 - 00:20:09
Dernière modification le : vendredi 22 mars 2019 - 01:39:14

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Eric Mattmann, François Mathey, Alain Sevin, Gilles Frison. De-aromatizing Phosphole. Journal of Organic Chemistry, American Chemical Society, 2002, 67, pp.1208-1213. ⟨10.1021/jo0108156⟩. ⟨hal-00463046⟩



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