Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 52, Pages 14929-14934Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201102463
Keywords
density functional calculations; hydrogen bonds; multicomponent reactions; nucleophilic aromatic substitution; Ugi-Smiles reaction
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Funding
- ENS de Lyon
- ENSTA
- [ANR-08-CP2D-15-02]
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The effect of hydrogen bonds on the fate of nucleophilic aromatic substitutions (SNAr) has been studied in silico using a density functional theory approach in the condensed phase. The importance of these hydrogen bonds can explain the built-in solvation model of Bunnett concerning intermolecular processes between halogenonitrobenzenes and amines. It is also demonstrated that it can explain experimental results for a multicomponent reaction (the UgiSmiles coupling), involving an intramolecular SNAr (the Smiles rearrangement) as the key step of the process. Modeling reveals that when an intramolecular hydrogen bond is present, it lowers the activation barrier of this step and enables the multicomponent reaction to proceed.
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