Generation, structure and reactivity of arynes: A theoretical study |
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Authors: | Peter G. S. Dkhar and R. H. Duncan Lyngdoh |
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Affiliation: | (1) Department of Chemistry, North-Eastern Hill University, Bijni Complex, 793 003 Shillong, India |
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Abstract: | The semiempirical AM1 SCF-MO method is used to study the benzyne mechanism for aromatic nucleophilic substitution of various m-substituted chlorobenzenes and 3-chloropyridine. The calculations predict that most of the fixed substituents studied here would induce the formation of 2,3-arynes through their electron-withdrawing resonance or inductive effects. The geometry and electronic structure of the 2,3- and 3,4-arynes investigated here, confirm the generally acceptedo-benzyne structure postulated for arynes. The sites of nucleophilic addition to arynes as predicted here are in fair agreement with expectation and experimental findings. |
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Keywords: | Benzyne mechanism aryne bond nucleophilic addition to arynes AM1 SCF-MO method |
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