Polycondensation of an Elastomeric Polyester with an Antibacterial Activity in a Deep Eutectic Solvent: Numerical Study

Abstract

Deep eutectic solvents(DESs)were computationally designed(in-silico)using combinations of three quaternary ammonium salts(tetramethyl ammonium chloride(TMAC),choline chlorine (ChCl)and betaine)as hydrogen-bond acceptors(HBAs)with(sorbitol, glycerol, urea,ethylene glycol,glucose,acetic-acid,caffeic acid and 1,2-butanediol) hydrogen-bond donors(HBDs).The interaction mechanisms between the HBAs and HBDs were predicted and interaction energies were calculated by means of Conductorlike Screening Model for Real Solvents(COSMO-RS) theory.The results showed that the most appropriate pairing system was Betaine:Caffeic acid DES,presenting the strongest molecular interactions. Then,a theoretical study was conducted on the components involved in the green synthesis of poly(1,10-decane-citrate)polyester(PD10CA).The process involves dodecyldimethylbenzylamonium chloride(DDBAC)as HBA component of the DES,with 1,10-decanediol as HBD(monomer)and citric acid as co-monomer.After polymerization,the DDBAC served as filler.The molecular interactions between the DES components(HBA and HBD), citric acid in the DES,and DDBAC with PD10CA,and the polymerphysicochemical properties were implemented in-silico using COSMO-RS and DFT program within COSMOtherm software.The results showed that the interaction of DDBAC with DDO,and PD10CA with DDBAC,are mainly VAN DER WAALS’ bonds,while CA interacts mainly through H-bonding. These interactions also confirm the appropriate pairing of HBA-HBD, matrix-filler, and solvent-solute,respectively.