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A family of silatrane‐armed triazole‐encapped salicylaldehyde‐derived Schiff bases: Synthesis, spectral analysis, and antimicrobial and quantum chemical evaluation
Author(s) -
Singh Gurjaspreet,
Arora Aanchal,
Rani Sunita,
Kalra Pooja,
Aulakh Darpandeep,
Wriedt Mario
Publication year - 2017
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3728
Subject(s) - salicylaldehyde , chemistry , antimicrobial , schiff base , quantum chemical , triazole , polymer chemistry , combinatorial chemistry , organic chemistry , molecule
This work describes the successful synthesis of salicylaldehyde‐derived Schiff base‐linked organosilicon compounds following a highly efficient click approach. Hydroxyl‐terminated Schiff bases were alkylated to bis‐acetylenes ( 1 – 3 ) which upon 3 + 2 cycloaddition with 3‐azidopropyltriethoxysilane yielded triazole‐decorated bis‐silanes ( 4 – 6 ). These silanes further underwent base‐catalyzed transesterification to afford Schiff base‐linked triazole‐bound organosilatranes ( 7 – 9 ). The final silatranes as well as precursor alkynes and silanes were comprehensively characterized using NMR ( 1 H and 13 C) and infrared spectroscopic techniques together with elemental analysis and mass spectrometry of compounds 7 – 9 . Also, the structures of alkynes 1 – 3 and silatrane 7 were validated using single‐crystal X‐ray crystallography. Organosilatranes were initially screened for their pharmacokinetic profile using absorption, distribution, metabolism, excretion and toxicity (ADMET) tools and then explored for their antimicrobial activities, with compound 9 emerging as the most potent antimicrobial agent. Compounds 1 – 3 and 7 – 9 also underwent thorough computational analysis by applying the density functional theory (DFT) approach with B3LYP/6‐31G(d) level of theory and the results were found to be consistent with the experimental data. Several DFT‐based descriptors were also evaluated providing a valuable insight into molecular stability and reactivity.