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1,3,5-三氮杂-7-磷杂金刚烷(PTA)的机械化学 P-衍生化及由此衍生的膦甜菜碱与银基配位聚合物的合成。

Mechanochemical P-derivatization of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Silver-Based Coordination Polymers Obtained from the Resulting Phosphabetaines.

机构信息

Department of Physical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary.

Doctoral School of Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary.

出版信息

Molecules. 2020 Nov 16;25(22):5352. doi: 10.3390/molecules25225352.

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(CFSO) 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 () formed with the glutaconyl derivative of PTA () showed considerable antimicrobial activity against both Gram-negative and Gram-positive bacteria and yeast strains.

摘要

我们之前曾描述过,在水溶液中,1,3,5-三氮杂-7-磷金刚烷(PTA)与马来酸反应生成了一种膦烷酸酯两性离子。与 2-甲基马来酸(柠康酸)的相同反应进行得要慢得多。在这里报告的是,对于谷氨酸和衣康酸(柠康酸的结构异构体),形成相应的磷甜菜碱所需的反应时间明显更短。新的磷甜菜碱通过元素分析、多核 NMR 光谱和 ESI-MS 光谱进行了分离和表征。此外,它们在固态下的分子结构通过单晶 X 射线衍射(SC-XRD)确定。使用行星球磨机,也可以通过机械化学方法从 PTA 和不饱和二羧酸合成磷甜菜碱,并且比较了溶剂和无溶剂条件下合成的特点。在水溶液中,新的磷甜菜碱与 Ag(CFSO)反应生成了基于 Ag(I)的配位聚合物。根据 SC-XRD 结果,在这些聚合物中,Ag(I)离子与配体的 N 和 O 供体原子配位;然而,也确定了 Ag(I)-Ag(I)相互作用。与 PTA 的谷氨酸酯衍生物()形成的基于 Ag(I)的配位聚合物()对革兰氏阴性和革兰氏阳性细菌和酵母菌株均显示出相当的抗菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/036a/7697749/10c949b42454/molecules-25-05352-g001.jpg

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