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Does alpha-effect exist in E2 reactions? A G2(+) investigation.

Yi Ren1, Hiroshi Yamataka

  • 1College of Chemistry, Key Laboratory of Green Chemistry and Technology, Ministry of Education, and Key State Laboratory of Biotherapy, Sichuan University, Chengdu 610064, People's Republic of China. yiren57@hotmail.com

Journal of Computational Chemistry
|July 10, 2008
PubMed
Summary
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Gas-phase elimination reactions show an "alpha-effect" due to lone pair electrons, influencing reaction barriers. This effect differs between elimination (E2) and substitution (SN2) reactions based on base structure.

Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • The alpha-effect, an enhancement in reactivity for species with lone pairs adjacent to the reacting center, is well-documented.
  • Its manifestation in gas-phase bimolecular elimination (E2) reactions requires further elucidation.

Purpose of the Study:

  • To investigate the alpha-effect in gas-phase E2 reactions using high-level computational theory.
  • To compare the behavior of alpha-bases with adjacent lone pairs to normal bases in E2 reactions.

Main Methods:

  • Utilized G2(+) theory for high-level ab initio calculations.
  • Examined the reactions of 13 different bases with ethyl chloride.

Main Results:

Related Experiment Videos

  • Identified downward deviations from established correlations for alpha-bases, confirming the alpha-effect in gas-phase E2 reactions.
  • Observed that the magnitude of the alpha-effect in E2 reactions varies less within a periodic table column compared to SN2 reactions.
  • Attributed the alpha-effect to favorable orbital interactions between lone pairs and anti-bonding orbitals.

    • Conclusions:

    • The alpha-effect is present in gas-phase E2 reactions and originates from electronic orbital interactions.
    • The behavior of the alpha-effect in E2 reactions shows distinct trends compared to SN2 reactions, influenced by the periodic nature of alpha-atoms.
    • Electron-rich pi lobes, not just lone pairs, can also induce the alpha-effect in E2 reactions.