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Transition State Stabilization by SCF2 -H⋅⋅⋅O Bifurcated Hydrogen Bond.

Jingjing Zhang1, Yingbo Shao2, Hanliang Zheng2

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Summary

The difluoromethylthio group (SCF2H) acts as a weak hydrogen bond donor. Researchers found evidence of a bifurcated hydrogen bond stabilizing transition states in difluoromethylthiolating reactions.

Keywords:
DFT calculationbifurcated hydrogen bonddifluoromethylthiolating reagentkineticstransition state stabilization

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • The difluoromethylthio group (SCF2H) is lipophilic and a weak hydrogen bond donor.
  • This group is of significant interest to the pharmaceutical and agrochemical industries.
  • Literature on SCF2H hydrogen bonding interactions is limited.

Purpose of the Study:

  • To determine the hydrogen bond acidity parameter (A) of the SCF2H group.
  • To investigate the role of SCF2H hydrogen bonding in electrophilic difluoromethylthiolating reagents.
  • To explore the impact of these interactions on reaction mechanisms and reactivity.

Main Methods:

  • Kinetic studies of difluoromethylthiolating reactions.
  • Computational chemistry methods (e.g., DFT) to model transition states and interactions.
  • Analysis of solvent effects on hydrogen bonding.

Main Results:

  • Determination of the hydrogen bond acidity parameter (A) for SCF2H.
  • Identification of a stabilizing RSCF2-H···O2 bifurcated hydrogen bond in the transition state.
  • Observation of potential reversals in electrophilic reactivity compared to trifluoromethylthiolating reagents.

Conclusions:

  • The SCF2H group's hydrogen bonding capabilities are significant in chemical reactions.
  • Bifurcated hydrogen bonds play a crucial role in stabilizing transition states for SCF2H transfer.
  • Understanding these interactions is key to designing novel reagents and predicting reactivity.