engleski

Structural studies of substituted oxazolidinones by spectroscopic and quantum chemical methods

Oxazolidinones belong to an important class of aliphatic heterocycles with interesting biological properties, such as antimicrobial, psychotropic, anticoagulant, anticancer, fungicidal and antithyroid activities. Their solution- and solid-state structures are stabilized by intermolecular hydrogen bonds through NH and carboxyl moieties, which act as hydrogen bond donors and acceptors, respectively. Obtaining a detailed insight into the structure and dynamics of these interactions is a major prerequisite for the design of new drugs with enhanced biological properties. In this research we applied a combination of 1D and 2D NMR techniques, vibrational spectroscopy and quantum chemical calculations to study the structure and hydrogen bonding of bioactive oxazolidinones. It has been observed that in low polarity solvents, such as chloroform, dimers are formed presumably by intermolecular hydrogen bonds between oxazolidinone molecules forming the most stable complexes, which has also been found in the solid state (Figure 1a). In more polar solvents, like dimethylsulfoxide and methanol, intermolecular interactions with solvent molecules prevail. Changing the solution concentration considerably affected oxazolidinone resonances only in chloroform, further confirming the dimer formation (Figure 1b).

oxazolidinones ; hydrogen bonding ; solution and solid state structure ; NMR spectroscopy ; vibrational spectroscopy ; quantum chemical calculations

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