Synthesis, spectroscopic and electrochemical characterization of secnidazole esters

• Published in: Journal of molecular structure Vol. 1149; pp. 792 - 802
• Main Authors: Shahid, Hafiz Abdullah, Jahangir, Sajid, Hanif, Muddasir, Xiong, Tianrou, Muhammad, Haji, Wahid, Sana, Yousuf, Sammer, Qureshi, Naseem
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.12.2017
• Subjects: EIMS fragmentation; Electrochemistry; Hetero atom; NMR prediction; Spectroscopic characterization; Synthesis; Hetero atom; Electrochemistry; Spectroscopic characterization; Synthesis; NMR prediction; EIMS fragmentation
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2017.08.036

We report a low-cost, less toxic to environment and simple method for the esterification of secnidazole. This is first comprehensive structural characterization of novel secnidazole esters by the spectroscopic and electrochemical methods. The important EIMS fragmentation analysis showed unique contribution of heteroatom bonds explained by the fragmentation patterns. These peaks originate from the loss of single electron, loss of HCN, M-O, M-NO, M-NO2, M-C7H10N3O3, and M-C8H10N3O4. The comparison of 13C NMR predicted values with the experimental values showed that ChemBioDraw Ultra 14.0 has advantage of predicting aromatic (sp2) carbons, while MestReNova 6.1 predicts sp3 hybrid carbons more accurately. The electrochemical properties indicated an irreversible oxidation process and reversible reduction process in these ester molecules similar to the parent secnidazole. [Display omitted] •A low-cost synthesis method, for the esterification of secnidazole is explained in detail.•Secnidazole esters were studied by the spectroscopic and cyclic voltammetry.•ChemBioDraw Ultra 14.0 has the advantage of predicting aromatic (sp2) carbons, while MestReNova 6.1 predicts sp3 hybrid carbons more accurately.•The EIMS fragmentation analysis showed unique fragmentation patterns.