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Hyperconjugative effects in π-hydrogen bonding: Theory and experiment.

Boris Galabov1,2, Valia Nikolova1, Diana Cheshmedzhieva1

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|November 9, 2017
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Summary

This study investigates π-hydrogen bonded complexes between substituted phenols and hexamethylbenzene. Methyl groups significantly enhance hydrogen bonding, doubling the O-H stretching frequency shifts compared to benzene complexes.

Keywords:
OH stretching frequencydensity functional theory computationshexamethylbenzenehyperconjugationsubstituted phenolsπ-hydrogen bonding

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Spectroscopy

Background:

  • π-Hydrogen bonding plays a crucial role in molecular interactions.
  • Understanding substituent effects on non-covalent interactions is vital.
  • Hexamethylbenzene offers a unique platform to study steric and electronic effects.

Purpose of the Study:

  • To investigate the properties of π-hydrogen bonded complexes between substituted phenols and hexamethylbenzene.
  • To quantify the impact of methyl hyperconjugative effects on interaction energies and O-H stretching frequencies.
  • To elucidate the mechanisms governing these methyl hyperconjugative effects.

Main Methods:

  • Density functional theory (DFT) computations using the B3LYP/6-311++G(2df,2p) method.
  • Infrared (IR) spectroscopy for experimental validation.
  • Analysis of Hirshfeld charges, electrostatic potentials, and molecular electrostatic potential maps.

Main Results:

  • Twenty π-hydrogen bonded complexes with T-shaped structures were characterized.
  • Theoretical computations accurately predicted O-H stretching frequency shifts (ΔνOH).
  • ΔνOH shifts in hexamethylbenzene complexes were approximately twice as large as in benzene complexes, indicating enhanced hydrogen bonding.

Conclusions:

  • Methyl hyperconjugative effects significantly strengthen π-hydrogen bonding in phenol-hexamethylbenzene complexes.
  • The enhanced hydrogen bonding is attributed to electronic contributions from methyl groups.
  • Computational methods provide reliable predictions for these non-covalent interactions.