Synthesis, X-ray crystallographic studies, DFT calculations and nanostructural features of annulated imidazo[4,5-b]pyridine derivatives

ABSTRACT

Friedländer-type condensation of 5-amino-4-cyano-1-(phenyl/p-substitutedphenyl)imidazole with cycloalkanone was done by refluxing the mixture with a suspension of anhydrous aluminum chloride in dry 1,2-dichloroethane to produce 7-amino-3-aryl(5,6)cycloalkanoimidazolo[4,5-b]pyridine. Single X-ray crystallographic diffraction studies had shown that compounds had different types of heterodimeric, homodimeric π–π stacking, T-type stacking, and intermolecular hydrogen bonds which lead to nanostructure formation detected by scanning electron microscope. DFT calculation had also been performed to quantify heterodimeric π–π and T-stacking interactions.

GRAPHICAL ABSTRACT

KEYWORDS:

• DFT calculation
• Friedländer condensation
• imidazo[4,5-b]pyridine derivatives
• morphological diversity
• X-ray crystallographic study

Acknowledgments

The author (A. D.) thanks the University of Calcutta for providing laboratory and spectroscopic facilities. I thank Prof. (retd.) Sibdas Ray, Dr. Kaliprasanna Dhara of Chemistry Dept., University of Calcutta for their support. Single X-ray Crystallographic studies had been performed with Single Crystal Diffractometer Facilities offered by DST-FIST programme, at the Chemistry Dept., C.U. The author thanks Centre for Research in Nanoscience & Nanotechnology of University of Calcutta for scanning electron microscopic study. The author thanks the Council of Scientific and Industrial Research, New Delhi, India for financial support.

Additional information

Funding

This work was supported by CSIR, New delhi [Grant number 09/028(0795)/2010-EMR-1].