Article ID Journal Published Year Pages File Type
1402382 Journal of Molecular Structure 2014 10 Pages PDF
Abstract

•Four new compounds are characterised using IR, mass and advanced NMR techniques.•Compounds showed doubling of all the signals due to syn and anti rotamers at RT.•The energy barrier for N-CO rotation of one of the compounds was determined.•The equilibrium observed between the syn rotamer of TB1 and anti rotamer of TB2.•All the compounds were screened for their antibacterial & antifungal activities.

A new series of N-formyl-2,6-bis(4-methoxyphenyl)piperidin-4-ones 5–8 has been synthesized and characterised using IR, mass and 1H, 13C, DEPT and 2D (COSY and HSQC) NMR spectral techniques. The NMR spectral data indicated that the N-formylpiperidin-4-ones 5–8 prefer to exist in a conformational equilibrium between a syn rotamer with a twist boat conformation (TB1) and an anti rotamer with a twist boat conformation (TB2) in solution. The stereodynamics of these systems have been studied by recording the dynamic 1H NMR spectra of compound 5, and the energy barrier for the N-CO rotation was determined to be 64.3 kJ/mol. All of the synthesized compounds (5–8) were screened for their biological activity.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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