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Chemical Research in Chinese Universities

, Volume 33, Issue 5, pp 765–772 | Cite as

Theoretical and experimental study of the reaction of 2-guanidinobenzimidazole on a series of meta-substituted benzaldehydes

  • Chebbi Monia
  • Chebbi Hammouda
  • M’rabet Hedi
  • Arfaoui Youssef
Article

Abstract

The syntheses of a variety of 1,3,5-triazinebenzimidazoles obtained by the cyclocondensation reaction of 2-guanidinobenzimidazole with a series of meta-substituted benzaldehydes were reported. The prepared compounds were fully characterized by IR and NMR spectroscopies. Based on the density functional theory(DFT) calculations method, quantum chemical calculations were performed by Gaussian 09 set of programs. All possible transition states, reactants and products were fully optimized at the hybrid density functional B3LYP level using the 6-311+G(d,p). The geometries of five possible tautomers of 2-amino-4-aryl[1,3,5]triazino[1,2-a]benzimidazoles were optimized in ethanol, using conductor like polarizable continuum(CPCM) in the gas phase. The energetic diagrams of tautomeric equilibrium showed that form A is the most stable tautomer which proved to be in accordance with the X-ray diffraction structure analysis. In order to interpret the reaction mechanism, the chemical reactivity was studied using local and global reactivity indexes.

Keywords

2-Amino-4-aryl[1,3,5]triazino[1,2-a]benzimidazole 2-Guanidinobenzimidazole Density functional theory Tautomeric equilibrium Reaction mechanism X-Ray diffraction analysis 

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Supplementary material

40242_2017_6476_MOESM1_ESM.pdf (610 kb)
A combined experimental and DFT study of the meta-substituent effects on the formation of 2-amino-4-aryl[1,3,5]triazino[1,2-a] benzimidazoles

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Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany 2017

Authors and Affiliations

  • Chebbi Monia
    • 1
  • Chebbi Hammouda
    • 2
  • M’rabet Hedi
    • 3
  • Arfaoui Youssef
    • 1
  1. 1.Unit of Physical Chemistry of Condensed MaterialsUniversity of Tunis El-ManarTunisTunisia
  2. 2.Laboratory of Materials Crystallochemistry and Applied ThermodynamicUniversity of Tunis El-ManarTunisTunisia
  3. 3.Laboratory of Organic and Heterocyclic Synthesis, Department of Chemistry, Faculty of SciencesUniversity of Tunis El-ManarTunisTunisia

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