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Weak interactions as diagnostic tools for inductive effects.

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This study introduces a novel method using halogen-bonded and dative covalent complexes to measure substituent inductive effects. The findings reveal that these inductive effects are not always additive, challenging previous assumptions.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Organic Chemistry

Background:

  • A universally applicable measure for substituent inductive effects, beyond substituted benzenes, is lacking.
  • Weak interactions offer potential as tools for quantifying electronic effects.

Purpose of the Study:

  • To assess the viability of halogen bonding (I···N) and dative covalent bonding (Ge···N) for measuring inductive effects of diverse substituents.
  • To establish a reliable ordering of substituents based on their inductive influence.

Main Methods:

  • Computational modeling using MP2(full) and M06-2X levels of theory.
  • Analysis of interatomic separations in model complexes (F3CI···NH2R and FH3Ge···NH2R).
  • Minimization of steric and resonance effects by using monosubstituted bases (NH2R).

Main Results:

  • Both halogen bonding and dative covalent bonding modes provide consistent qualitative ordering of substituent inductive effects.
  • The inductive effects of substituents were found to be generally non-additive.
  • Trisubstituted bases (NR3) can sometimes reverse the electronic effects observed with monosubstituted bases.

Conclusions:

  • Halogen-bonded and dative covalent complexes serve as effective probes for substituent inductive effects.
  • The non-additive nature of inductive effects necessitates careful consideration in molecular design.
  • A quantitative ordering of substituents based on their inductive tendencies is presented.