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Bicarbonate Recognition Features of a Naphthobipyrrole‐strapped Calix[4]pyrrole
Bulletin of the Korean Chemical Society ( IF 2.3 ) Pub Date : 2020-11-27 , DOI: 10.1002/bkcs.12159 Ju Hyun Oh 1 , Ju Ho Yang 1 , Han‐Byeol Choi 1 , Sung Kuk Kim 1
Bulletin of the Korean Chemical Society ( IF 2.3 ) Pub Date : 2020-11-27 , DOI: 10.1002/bkcs.12159 Ju Hyun Oh 1 , Ju Ho Yang 1 , Han‐Byeol Choi 1 , Sung Kuk Kim 1
Affiliation
A calix[4]pyrrole (1) strapped with a naphthobipyrrole was prepared and its ability to bind the bicarbonate anion (HCO3−) was investigated via 1H NMR and UV/Vis spectroscopic analyses. The resulting spectral data revealed that receptor 1 was capable of recognizing HCO3− with high affinity in solutions as well as in the solid state. In CD2Cl2, it was inferred from 1H NMR spectroscopic titration experiment that HCO3− interacts with receptor 1 via two different modes with the first involving HCO3− being hydrogen bonded to all six NH protons of the receptor. This interaction is followed by a deprotonation process of the bipyrrole NHs upon the subsequent addition of HCO3− while the anion remains hydrogen‐bonded to the calix[4]pyrrole NHs. In the presence of methanol, the bound bicarbonate anion was converted into an unstable monomethyl carbonate anion (CH3OCO2−) that was then stabilized by forming a complex with receptor 1.
中文翻译:
萘并吡咯环的杯[4]吡咯的碳酸氢盐识别特征
杯[4]吡咯(1)用制备一种naphthobipyrrole和其结合的碳酸氢根阴离子的能力(HCO绑3 - )通过研究1 H NMR和UV /可见光分光分析。将得到的光谱数据表明,受体1是能够识别的HCO 3 -以高亲和力在解决方案,以及在固体状态。在CD 2氯2,将其从推断1个1 H NMR光谱滴定实验的是HCO 3 -与受体相互作用1经由与第一涉及HCO两种不同的模式3 -被氢键合到受体的所有六个NH质子上 这种相互作用之后是在随后加入HCO的二吡咯NHS的脱质子化过程3 - ,而阴离子保持氢键结合到杯[4]吡咯NHS。在甲醇的存在下,结合的碳酸氢根阴离子被转化成不稳定的单碳酸根阴离子(CH 3 OCO 2 - ),然后将其通过形成复合物与受体稳定1。
更新日期:2021-01-27
中文翻译:
萘并吡咯环的杯[4]吡咯的碳酸氢盐识别特征
杯[4]吡咯(1)用制备一种naphthobipyrrole和其结合的碳酸氢根阴离子的能力(HCO绑3 - )通过研究1 H NMR和UV /可见光分光分析。将得到的光谱数据表明,受体1是能够识别的HCO 3 -以高亲和力在解决方案,以及在固体状态。在CD 2氯2,将其从推断1个1 H NMR光谱滴定实验的是HCO 3 -与受体相互作用1经由与第一涉及HCO两种不同的模式3 -被氢键合到受体的所有六个NH质子上 这种相互作用之后是在随后加入HCO的二吡咯NHS的脱质子化过程3 - ,而阴离子保持氢键结合到杯[4]吡咯NHS。在甲醇的存在下,结合的碳酸氢根阴离子被转化成不稳定的单碳酸根阴离子(CH 3 OCO 2 - ),然后将其通过形成复合物与受体稳定1。