articleJournal of the American Chemical SocietyJul 10, 2008Closed access

Theory of 1,3-Dipolar Cycloadditions: Distortion/Interaction and Frontier Molecular Orbital Models

DHDaniel H. EssKNK. N. Houk

University of California, Los Angeles

PubMed
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Abstract

Quantum chemical calculations of activation barriers and reaction energies for 1,3-dipolar cycloadditions by the high-accuracy CBS-QB3 method reveal previously unrecognized quantitative trends in activation barriers. The distortion/interaction model of reactivity explains why (1) there is a monotonic decrease of approximately 6 kcal/mol in the activation energy along the series oxides, imine, and ylide for the diazonium, nitrilium, and azomethine betaine classes of 1,3-dipoles; (2) nitrilium and azomethine betaines with the same trio of atoms have almost identical cycloaddition barrier heights; (3) barrier heights for the cycloadditions of a given 1,3-dipole with ethylene and acetylene have the same activation…

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Topics & keywords

Topics
Keywords
  • Chemistry
  • Reactivity (psychology)
  • Dipole
  • Molecular orbital
  • Transition state
  • Computational chemistry
  • Cycloaddition
  • 1,3-Dipolar cycloaddition
UN Sustainable Development Goals
  • Affordable and clean energy
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