Abstract
We have described earlier that in aqueous solutions, the reaction of 1,3,5-triaza-7-phosphaadamantane (PTA) with maleic acid yielded a phosphonium-alkanoate zwitterion. The same reaction with 2-methylmaleic acid (citraconic acid) proceeded much slower. It is reported here, that in the case of glutaconic and itaconic acids (constitutional isomers of citraconic acid), formation of the corresponding phosphabetaines requires significantly shorter reaction times. The new phosphabetaines were isolated and characterized by elemental analysis, multinuclear NMR spectroscopy and ESI-MS spectrometry. Furthermore, their molecular structures in the solid state were determined by single crystal X-ray diffraction (SC-XRD). Synthesis of the phosphabetaines from PTA and unsaturated dicarboxylic acids was also carried out mechanochemically with the use of a planetary ball mill, and the characteristics of the syntheses in solvent and under solvent-free conditions were compared. In aqueous solutions, the reaction of the new phosphabetaines with Ag(CF3SO3) yielded Ag(I)-based coordination polymers. According to the SC-XRD results, in these polymers the Ag(I)-ion coordinates to the N and O donor atoms of the ligands; however, Ag(I)-Ag(I) interactions were also identified. The Ag(I)-based coordination polymer (CP1.2) formed with the glutaconyl derivative of PTA (1) showed considerable antimicrobial activity against both Gram-negative and Gram-positive bacteria and yeast strains
Highlights
Even in the case of water there is a possibility to contaminate the environment we reported the mechanochemical synthesis of Rh(I)-bis-NHC (NHC = N-heterocyclic carbene) with spent solvent
We have we reported the mechanochemical synthesis of Rh(I)-bis-NHC (NHC = N-heterocyclic carbene) successfully performed the reactions of PTA and alkyl halides in a planetary ball mill
We conceived that the PTA-derived phosphabetaines may form complex coordination polymers successfully performed the reactions of PTA and alkyl halides in a planetary ball mill
Summary
The mechanochemical reactions are performed in planetary or vibrational high purity, isolated N-alkyl-PTA products were higher than those obtained with the use of organic ball mills (pbm and vbm, respectively), and the reaction conditions can be finely tuned by proper solvents [35]. We conceived that the PTA-derived phosphabetaines may form complex coordination polymers successfully performed the reactions of PTA and alkyl halides in a planetary ball mill. The yields of with silver(I) due to the simultaneous presence of three N donor atoms and two carboxylate groups high purity, isolated N-alkyl-PTA products were higher than those obtained with the use of organic solvents [35]. We conceived that the PTA-derived phosphabetaines may form complex coordination polymers with silver(I) due to the simultaneous presence of three N donor atoms and two carboxylate in the same molecule.
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