Theoretical investigation of the selectivity in intramolecular cyclizations of some 2'-aminochalcones to dihydroquinolin-8-ones and indolin-3-ones

Andres Reyes, Paola Andrea Cuervo, Fabian Orozco, Rodrigo Abonia, Mario Duque-Noreña, Patricia Pérez, Eduardo Chamorro

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The selectivity of the intramolecular cyclizations of a series of 2'-aminochalcones was investigated with an approach that combines spin-polarized conceptual density functional theory and energy calculations. To that aim, condensed-to-atoms electrophilic Fukui functions, f NN + (r), were utilized as descriptors of the proclivity for nucleophilic attack of the NH2 group on the unsaturated α and β carbons. The results of our model are in excellent agreement with the experimental available evidence permitting us in all cases to predict when the cyclization processes led to the formation of 5-exo and 6-endo products. [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)3611-3618
Number of pages8
JournalJournal of Molecular Modeling
Volume19
Issue number9
DOIs
Publication statusPublished - Sep 2013

Keywords

  • 2'-aminochalcones
  • 6-endo-end and 5-exo-trig closures
  • SP-DFT Fukui function

ASJC Scopus subject areas

  • Catalysis
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Computational Theory and Mathematics
  • Inorganic Chemistry

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