Romanian Society of Pharmaceutical Sciences

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SYNTHESIS, PHYSICO-CHEMICAL CHARACTERISATION AND MESOMORPHIC PROPERTIES OF SOME NOVEL AZODERIVATIVES

GABRIELA RĂU1, GEORGE DAN MOGOŞANU2*, CĂTĂLINA GABRIELA PISOSCHI3, CAMELIA ELENA STĂNCIULESCU3

University of Medicine and Pharmacy of Craiova, Faculty of Pharmacy, 2 Petru Rareş Street, 200349 Craiova, Romania
1.Department of Organic Chemistry, Medicinal Chemistry
2.Department of Pharmacognosy & Phytotherapy
3.Department of Biochemistry

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The synthesis of some novel compounds, four 4-(N-phenylacetamidoxy)azobenzenes and one 4-(N-phenylacetamidoxy)-4’-(phenylazo)biphenyl, was completed through the condensation of the 4-(phenylazo)phenols or 4-hydroxy-4’-(phenylazo) biphenyl, in alkaline medium, with 4-methoxy-N-chloroacetylaniline. The purification of the compounds was achieved by recrystallisation from toluene and checked by gas chromatography. The compounds are solid, with different colours and high melting points. Their structures were established through elemental and spectral analysis (UV–Vis, FTIR, 1H–NMR, GC–MS). For the novel synthesized azoderivatives, the mesomorphic behaviour was studied by polarizing optical microscopy (POM) and differential scanning calorimetry (DSC). It was found that the size, position and polarity of the terminal group strongly influence the type of mesophase and the transition temperatures of a given compound.