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Computational Study of the Donor-Acceptor Interactions Underlying the Variable Oxygen Probe.

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  • 1School of Chemistry and Bio21 Institute, University of Melbourne, Parkville, VIC 3010, Australia.

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The variable oxygen probe (VOP) technique quantifies electron donor abilities. Gas-phase calculations show VOP slopes correlate with donor-acceptor interactions, but experimental data offers superior discrimination.

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Area of Science:

  • Computational Chemistry
  • Crystallography
  • Organic Chemistry

Background:

  • The variable oxygen probe (VOP) is a crystallographic method for assessing electron donor abilities.
  • Donor abilities are influenced by various electronic features, including lone pairs, polarized bonds, π systems, and strained C-C bonds.

Purpose of the Study:

  • To computationally explore the donor-acceptor interactions fundamental to the VOP technique.
  • To compare gas-phase computational results with experimental crystallographic data for VOP analysis.

Main Methods:

  • Density functional theory (DFT) calculations were performed on model systems 1-13.
  • Natural bond orbital (NBO) analysis was used to examine donor-acceptor interactions with σ* antibonding orbitals.
  • VOP slopes were calculated and compared between gas-phase and crystal structure data.

Main Results:

  • Gas-phase VOP slopes qualitatively correlated with the sum of significant donor-acceptor interactions in derivatives 1-13.
  • Calculated C-OR bond distances showed a relationship with pKa(ROH) for various -OR substituents.
  • Gas-phase VOP slopes were smaller in magnitude than experimental values, suggesting disfavoring of the C+-OR valence form.

Conclusions:

  • Computational VOP analysis provides insights into donor-acceptor interactions.
  • Experimental VOP data offers more effective discrimination of donor abilities compared to gas-phase calculations.
  • The VOP technique's utility is highlighted by its ability to differentiate electronic properties effectively.