Abstract 1297: Synthesis and structural analysis on an ionic diphenyltin complex as a potential anticancer agent

Abstract

Abstract Triorganotins are popular among chemists due to their potential biological properties against bacteria, fungi, and cancer cell lines. However, they have limited applications due to their poor water solubility. We hypothesize that solubility can be improved when the complex exhibits partial ionic characteristics. Therefore, it is our research goal to synthesize triphenyltin complexes that possess ionic characteristics. Syntheses of the ionic triphenyltin complex involved the reaction of a diprotic carboxylic acid, with triphenyltin chloride in the presence of di-isopropylamine. However, a tin-carbon cleavage reaction was observed, as IR/NMR spectroscopy and X-ray Crystallography studies showed that an ionic diphenyltin complex was successfully obtained in the reaction. The ionic complex consists of a diphenyltin anionic moiety, two oxalate ligands are observed coordinating to the tin atom in the bidentate mode, and two diisopropylammonium as the counterions. The anionic diphenyltin moieties has a distorted octohedral geometry with two carbons and two oxygens atom occupying the equatorial positions and two oxygen atoms occupying the axial positions. The ionic complex is essentially a 1-D polymer chain through an extensive hydrogen-bonding network between the oxalate groups (OCO) and the N atom from the ammonium cations. Compared to the similar reaction with triphenyltin hydroxide, which resulted in ionic triphenyltin complexes, cleavage of one phenyl group was observed for the first time in the reaction with triphenyltin chloride. Future studies will be focused on the mechanistic studies on the Sn-C cleavage. Citation Format: Jade Witter, Xueqing Song, Tajera Henry, William Li. Synthesis and structural analysis on an ionic diphenyltin complex as a potential anticancer agent [abstract]. In: Proceedings of the American Association for Cancer Research Annual Meeting 2021; 2021 Apr 10-15 and May 17-21. Philadelphia (PA): AACR; Cancer Res 2021;81(13_Suppl):Abstract nr 1297.