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Related Experiment Videos

Hydrogen bonding interactions between indole and benzenoid-pi-bases.

M A Muñoz1, R Ferrero, C Carmona

  • 1Departamento de Química Física, Facultad de Farmacia, Universidad de Sevilla, 41012 Seville, Spain. asuncion@us.es

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
|December 13, 2003
PubMed
Summary

This study reveals that indole forms 1:1 complexes with aromatic bases like benzene, with interactions strengthening as base electron density increases. Higher concentrations suggest additional interactions, forming 1:2 complexes.

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Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Molecular Interactions

Background:

  • Non-covalent interactions are crucial in chemical and biological systems.
  • Understanding pi-pi and hydrogen bonding interactions is key to molecular recognition.

Purpose of the Study:

  • To investigate the NH-pi interactions between indole and various aromatic compounds.
  • To determine the stoichiometry and binding characteristics of these complexes.

Main Methods:

  • Fourier transform infrared (FTIR) spectroscopy was used to study indole solutions.
  • The NH stretching band of indole was monitored to detect complex formation.

Main Results:

  • 1:1 complexes of indole with benzene, naphthalene, phenanthrene, toluene, m-xylene, and mesitylene were identified.

Related Experiment Videos

  • NH frequency shifts indicated that methylation enhances electron density and strengthens interactions.
  • Association constants increased with the number of rings and methyl groups on the aromatic base.
  • Evidence for 1:2 complex formation at higher base concentrations was observed.

    • Conclusions:

    • Indole engages in NH-pi interactions with aromatic systems.
    • The strength of these interactions is influenced by the electron density and structure of the aromatic base.
    • Complex formation can extend beyond simple 1:1 stoichiometry, involving van der Waals forces.