A further exploration of a nucleophilicity index based on the gas-phase ionization potentials

Paula Jaramillo, Luis R. Domingo, Eduardo Chamorro, Patricia Pérez

Research output: Contribution to journalArticlepeer-review

246 Citations (Scopus)

Abstract

An empirical nucleophilicity index based on the gas-phase ionization potentials has been recently shown to be useful categorizing and settling the nucleophilicity power of a series of captodative ethylenes reacting in cycloaddition reactions (L.R. Domingo, E. Chamorro, P. Pérez, Journal of Organic Chemistry 73 (2008) 4615-4624). In the present work, the applicability of such model is tested within a broader series of substituted alkenes, substituted aromatic compounds and simple nucleophilic molecules. This index obtained within a Koopman's theorem framework has been evaluated here in both gas and solution phases for several well-known nucleophiles. These results are found to be linearly correlated. Finally, the feasibility of the predictive character of this index has been discussed in comparison to the available experimental nucleophilicities of some amines in water. These results further support and validate the usefulness of such approximation in the modeling of the global nucleophilicity.

Original languageEnglish
Pages (from-to)68-72
Number of pages5
JournalJournal of Molecular Structure: THEOCHEM
Volume865
Issue number1-3
DOIs
Publication statusPublished - 30 Sep 2008

Keywords

  • Electron-releasing group effects
  • Electron-withdrawing group effects
  • Electrophilicity
  • Gas-phase ionization potential
  • Nucleophilicity

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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