Synthesis, Structural and Antioxidant Properties of C-p-methoxyphenylcalix[4]resorcinarene

Abstract

The structure of Calix[4]resorcinarene is less reported compare to other calixarene derivatives because of its conformational flexibility and stability when exposed to air. The presence of solvent molecules is important for its stability in the solid state. On the other hand, the presence of several phenol groups make it a good candidate for antioxidant study. Some of them have also shown good antibacterial activity. p-methoxyphenyl calix[4]resorcinarene was synthesized and characterized by infrared and (1H , 13C) NMR spectroscopic techniques. After several attempts suitable crystals were obtained and with the help of a special oil an X-ray investigation was carried out at low temperature. The calix crystallized in triclinic system with space group Pī, a= 10.6958(5), b=13.5781(7), c=16,3334(8)A, α=68.284 (4), β= 74.275(5). γ=82.589(5)⁰, Z=2 and V= 2121.15(8)A3. The compound exhibits chair conformation with two resorcinol groups in anti-parallel position. The conformation is supported by eight DMSO and two DMF solvated molecules. It has a moderate antioxidant property.