Molecular interactions between pyrazine and n-propanol, chloroform, or tetrahydrofuran

Spectrochim Acta A Mol Biomol Spectrosc. 2008 Sep;70(4):793-8. doi: 10.1016/j.saa.2007.09.014. Epub 2007 Sep 25.

Abstract

The molecular interactions of pyrazine (PZ) with n-propanol, chloroform, and tetrahydrofuran (THF) have been investigated by employing ultraviolet spectroscopy and quantum chemical calculation methods. A new quantity, excess absorption coefficient, was introduced to represent the strength of the interaction. It was found that the interaction decreased in the order: PZ-propanol>PZ-chloroform>PZ-THF. The Benesi-Hildebrand method indicated that the interaction stoichiometries of the PZ-chloroform and PZ-THF systems were both 1:1 and the equilibrium constants were determined to be 2.07 and 0.64M(-1), respectively. Using a nonlinear fitting method, we demonstrated that the PZ-propanol was a two-step 1:2 interaction pair and the equilibrium constants were determined to be 8.8 and 0.19M(-1). Quantum chemical calculations showed the existence of hydrogen-bonding interactions in all the three system: normal Ncdots, three dots, centeredH-O hydrogen bond in the PZ-propanol system, unconventional Ncdots, three dots, centeredH-C hydrogen bond in the PZ-chloroform, and weak N-C-Hcdots, three dots, centeredO hydrogen bond in the PZ-THF system. Methodologically, we pointed out that special care must be taken when the Benesi-Hildebrand method is used to evaluate 1:2 interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Propanol / chemistry*
  • Chloroform / chemistry*
  • Furans / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Pyrazines / chemistry*
  • Spectrophotometry

Substances

  • Furans
  • Pyrazines
  • tetrahydrofuran
  • Chloroform
  • 1-Propanol