Synthesis, Spectroscopic Evaluations and UV-Vis Titration Studies of New Symmetrical Amide Compounds Derived from N-6-[(4-pyridylmethylamino)carbonyl]-pyridine-2-carboxylic Acid Methyl Ester

Trends in Sciences Pub Date : 2024-02-25 DOI:10.48048/tis.2024.7405

Maisara ABDUL KADIR, N.S.H. Haris, Hafiza MOHAMED ZUKI, Syara Kassim, K. Kassim

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Abstract

In this study, 2 flexible and pre-organized tetraamide compounds derived from N-6-[(4-pyridylmethylamino)carbonyl]-pyridine-2-carboxylic acid methyl ester namely 1,2-bis[N,N’-6-(4-pyridylmethylamido)pyridyl-2-carboxyamido]pentane (L1) and 1,2-bis[N,N’-6-(4-pyridylmethylamido)pyridyl-2-carboxyamido]hexane (L2) have been successfully synthesized when reacted with diamines in 1:2 ratio. These new compounds were built from combination of 3 main components, as a trend requires for anion receptor which are (i) 2,6-pyridine dicarboxamide moieties as targeted anion binding host, (ii) amino methyl pyridine pendants arms as the flexible moieties and (iii) pentyl (-C5H10-) and hexyl (-C6H12-) unit as the spacer. Compounds L1-L2 were fully characterized by using elemental analyzer, Fourier transform infrared (FTIR) spectroscopy, gas chromatography-mass spectroscopy (GC-MS), 1H, 2D NOESY and 13C Nuclear Magnetic Resonance (NMR) spectroscopies, and Ultraviolet-visible (UV-Vis) spectroscopies. In this study, anion titration methods were used to identify the affinity towards selected anions. The results showed that L1 (having a pentyl spacer) had the highest affinity towards phosphate anions as compared to L2, where the red shift changes were observed in the UV-vis spectrum at the amide region. HIGHLIGHTS Two novel amide compounds with flexible and pre-organized structure are designed for use as potential anion receptors The flexible moieties at the amide and the linker allow hydrogen bonding interaction of the molecules with variety anions with different geometries Anion titration studies revealed good affinities towards phosphate anions as suggested in Hofmeister trend GRAPHICAL ABSTRACT

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由 N-6-[(4-吡啶基甲基氨基)羰基]-吡啶-2-羧酸甲酯衍生的新型对称酰胺化合物的合成、光谱评估和紫外可见滴定研究

在这项研究中，从 N-6-[(4-吡啶基甲基氨基)羰基]-吡啶-2-羧酸甲酯衍生出 2 种柔性预组织四酰胺化合物，即 1,2-双[N、L1）和 1,2-双[N,N'-6-(4-吡啶基甲基氨基)吡啶-2-羧基氨基]己烷（L2）：2 的比例进行反应，成功合成了新化合物。这些新化合物由 3 种主要成分组合而成，阴离子受体的趋势要求这 3 种主要成分：(i) 2,6-吡啶二羧酰胺分子作为阴离子结合的目标宿主；(ii) 氨基甲基吡啶垂臂作为柔性分子；(iii) 戊基 (-C5H10-) 和己基 (-C6H12-) 单元作为间隔物。利用元素分析仪、傅立叶变换红外光谱（FTIR）、气相色谱-质谱（GC-MS）、1H、2D NOESY 和 13C 核磁共振（NMR）光谱以及紫外-可见光谱（UV-Vis）对 L1-L2 化合物进行了全面表征。本研究采用阴离子滴定法来确定对选定阴离子的亲和力。结果表明，与 L2 相比，L1（具有戊基间隔）对磷酸盐阴离子的亲和力最高，在酰胺区的紫外可见光谱中观察到红移变化。阴离子滴定研究表明，L1（具有戊基间隔物）对磷酸根阴离子具有很好的亲和力，而 L2（具有戊基间隔物）对磷酸根阴离子具有很好的亲和力。

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来源期刊

Trends in Sciences

CiteScore

1.20

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0.00%

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