Carbofunctional Silatrane Possessing Imidazole Moiety: Synthesis, Characterization, and Antibacterial Studies

GRAPHICAL ABSTRACT

Abstract

1-(3-(1-imidazol-1-yl)propyl)-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3.0]undecane 3, with imidazole functionality containing transannular N→Si bond (2.13 Å), was synthesized by transetherification reaction of triethanolamine 1 with N-(3-propyltriethoxysilane)imidazole 2. The compound was characterized by elemental analysis, spectroscopic techniques (IR, ¹H NMR, ¹³C NMR, UV–VIS), mass spectrometry, and X-ray diffraction. The thermal stability of silatrane 3 was studied by TGA/DTG/DSC techniques, which is in agreement with the mass spectrometry and X-ray diffraction studies. The structural investigations of 3 were complemented by quantum-chemical studies of the structure. Compound 3 showed slight activity against Escherichia coli and Staphylococcus aureus, while no activity was found against Bacillus subtillus and Vibrio cholera.

Keywords:

• Imidazole
• silatrane
• N-(3-propyltriethoxysilane)imidazole

Additional information

Funding

The authors are thankful to UGC, New Delhi (India) for providing financial support.