Intrinsic relative nucleophilicity of indoles

Eduardo Chamorro, Mario Duque-Noreña, Mar Ríos-Gutiérrez, Luis R. Domingo, Patricia Pérez

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The range of applicability of intrinsic (i.e., electronic) relative indices for quantifying electrophilicity and nucleophilicity responses (Chamorro et al. in J Phys Chem A 117(12):2636–2643, 2013) is extended to the characterization of coupling reactions of indoles with benzhydrylium ions and with the strongly electron-deficient heteroarene 4,6-dinitrobenzofuroxan. The reactivity categorization based on experimental kinetic evidence for such a electrophile/nucleophile coupling (Lakhdar et al. in J Org Chem 71(24):9088–9095, 2006) is rationalized in terms of purely electronic descriptors, revealing the polar nucleophilic activation of indole as a key factor associated with the initial rate-determining C–C coupling process.

Original languageEnglish
Article number202
JournalTheoretical Chemistry Accounts
Volume135
Issue number8
DOIs
Publication statusPublished - 1 Aug 2016

Keywords

  • Conceptual DFT
  • Electrophilicity
  • Indoles
  • Nucleophilicity
  • Polar organic reactions
  • Reactivity Scales

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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