Properties of a furan ring-opening reaction in aqueous micellar solutions for selective sensing of mesalazine

Abstract

A novel and efficient non-azo formation based method was developed for trace sensing of mesalazine (MES), a pharmaceutical aromatic amine. MES was simply coupled with a Meldrum’s activated furan (MAF) reagent via a furan ring opening reaction to form a colored product. The intense purple colored solution was detected at 575 nm. The reaction of MES with MAF was monitored by employing 1H NMR spectroscopy and mass spectrometry. In addition, density functional theory (DFT) was applied to optimize the structure of the colored product and its λmax (the wavelength of maximum absorbance) in dimethyl sulfoxide and water. The colored product was considered in three possible structures, and the most possible structures in dimethyl sulfoxide and in water were identified by employing the DFT calculations. Both of the most possible structures indicated only a local excitation in their λmax and no charge transfer was observed. However, one of the structures in dimethyl sulfoxide presented charge transfer properties occurring through NCCC moiety. A univariate optimization method was also used to attain the optimum condition for analysis. In addition, the dependence of the analytical response on the three main affecting parameters (reaction time (X1), Triton X-100 concentration (X2) and MAF concentration (X3)) was identified by employing a central composite design (CCD) approach. The CCD study showed that the analytical response depends complexly on the parameters. Beer’s law was obeyed within the range of 0.06–9.30 μg mL−1 of MES (155 fold linearity) at 575 nm, under the optimum condition introduced by the CCD approach. Also, the limit of detection was obtained 0.04 μg mL−1 of MES. The method showed precision (as relative standard deviation) and accuracy (as recovery) within the ranges of 0.6–3.2 % and 96.3–100.8%, respectively. Various organic and inorganic species, amino-pharmaceuticals, and amino acids were tested to evaluate the selectivity of the method. The selectivity of the analytical method was satisfactory. The method was successfully applied for detection of MES in various water matrices and pharmaceutical tablets.