Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting Phosphabetaines
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 glutac...
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MDPI AG
2020-11-01
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| author | Antal Udvardy Csenge Tamara Szolnoki Réka Gombos Gábor Papp Éva Kováts Ferenc Joó Ágnes Kathó |
| author_facet | Antal Udvardy Csenge Tamara Szolnoki Réka Gombos Gábor Papp Éva Kováts Ferenc Joó Ágnes Kathó |
| author_sort | Antal Udvardy |
| collection | DOAJ |
| description | 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(CF<sub>3</sub>SO<sub>3</sub>) 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 (<b>CP1.2</b>) formed with the glutaconyl derivative of PTA (<b>1</b>) showed considerable antimicrobial activity against both Gram-negative and Gram-positive bacteria and yeast strains |
| first_indexed | 2024-03-10T14:48:38Z |
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| spelling | doaj.art-3f3be3d8494049f790dd0e213a9b88e22023-11-20T21:09:18ZengMDPI AGMolecules1420-30492020-11-012522535210.3390/molecules25225352Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting PhosphabetainesAntal Udvardy0Csenge Tamara Szolnoki1Réka Gombos2Gábor Papp3Éva Kováts4Ferenc Joó5Ágnes Kathó6Department of Physical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryDepartment of Physical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryDepartment of Physical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryDepartment of Physical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryInstitute for Solid State Physics and Optics, Wigner Research Centre for Physics, Konkoly Thege Miklós u. 29-33, H-1121 Budapest, HungaryDepartment of Physical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryDepartment of Physical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryWe 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(CF<sub>3</sub>SO<sub>3</sub>) 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 (<b>CP1.2</b>) formed with the glutaconyl derivative of PTA (<b>1</b>) showed considerable antimicrobial activity against both Gram-negative and Gram-positive bacteria and yeast strainshttps://www.mdpi.com/1420-3049/25/22/5352antimicrobial activityball millcoordination polymermechanochemistryphosphonium saltsilver |
| spellingShingle | Antal Udvardy Csenge Tamara Szolnoki Réka Gombos Gábor Papp Éva Kováts Ferenc Joó Ágnes Kathó Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting Phosphabetaines Molecules antimicrobial activity ball mill coordination polymer mechanochemistry phosphonium salt silver |
| title | Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting Phosphabetaines |
| title_full | Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting Phosphabetaines |
| title_fullStr | Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting Phosphabetaines |
| title_full_unstemmed | Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting Phosphabetaines |
| title_short | Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting Phosphabetaines |
| title_sort | mechanochemical p derivatization of 1 3 5 triaza 7 phosphaadamantane pta and silver based coordination polymers obtained from the resulting phosphabetaines |
| topic | antimicrobial activity ball mill coordination polymer mechanochemistry phosphonium salt silver |
| url | https://www.mdpi.com/1420-3049/25/22/5352 |
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