Predicting the regioselectivity of nucleophilic addition to arynes using frontier molecular orbital contribution analysis

Frontier molecular orbital contribution analysis (FMO-CA) model is used for determining the regioselectivity of nucleophilic addition to substituted arynes. The nucleophile attacks the carbon possessing higher contribution of LUMO. [Display omitted] •Low cost computational method for predicting the...

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Bibliographic Details
Published in:Tetrahedron letters 2017-08, Vol.58 (34), p.3362-3365
Main Authors: Mirzaei, Saber, Khosravi, Hormoz
Format: Article
Language:English
Subjects:
Aryne
Contribution analysis
Frontier molecular orbital
Regioselectivity
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Summary:Frontier molecular orbital contribution analysis (FMO-CA) model is used for determining the regioselectivity of nucleophilic addition to substituted arynes. The nucleophile attacks the carbon possessing higher contribution of LUMO. [Display omitted] •Low cost computational method for predicting the regioselectivity of arynes.•Novel approach based on frontier molecular orbital (FMO) theory.•Reliable approach for altering the selectivity using the substituent effects. The regioselectivity of nucleophilic addition to substituted arynes was predicted using frontier molecular orbital contribution analysis. This model indicates that the percentage of the LUMO on the reacting terminus of the aryne is responsible for the observed regioselectivity; the nucleophile attacks the carbon possessing higher contribution of the LUMO.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.07.047