Anions are important hydrogen bond acceptors in a range of biological, chemical, environmental and medical molecular recognition processes. These interactions have been exploited for the design and synthesis of ditopic resorcinarenes as the hydrogen bond strength can be tuned through the modification of the substituent at the 2-position. However, many potentially useful compounds, especially those incorporating electron-withdrawing functionalities, have not been prepared due to the challenge of their synthesis: their incorporation slows resorcinarene formation that is accessed by electrophilic aromatic substitution. As part of our broader campaign to employ resorcinarenes as selective recognition elements, we need access to these specialized materials. In this article, we report a straightforward synthetic pathway for obtaining a 2-(carboxymethyl)-resorcinarene, and resorcinarene esters in general. We discuss the unusual conformation it adopts and propose that this arises from the electron-withdrawing nature of the ester substituents that renders them better hydrogen bond acceptors than the phenols, ensuring that each of them acts as a donor only. Density Functional Theory (DFT) calculations show that this conformation arises as a consequence of the unusual configurational isomerism of this compound and interruption of the archetypal hydrogen bonding by the ester functionality.

中文翻译：

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甲基酯2-间苯二芳烃的简明合成：一种椅型大环化合物

在一系列生物，化学，环境和医学分子识别过程中，阴离子是重要的氢键受体。这些相互作用已被用于设计和合成对位间苯二碳氮烯，因为可以通过在2位上取代基的修饰来调节氢键强度。然而，由于其合成的挑战，尚未制备出许多潜在有用的化合物，尤其是那些具有吸电子功能的化合物：它们的结合减慢了亲电子芳烃取代作用所产生的间苯二甲烯的形成。作为我们采用间苯二酚作为选择性识别元素的广泛运动的一部分，我们需要获得这些专门材料。在本文中，我们报告了获得2-（羧甲基）-间苯二芳烃和一般间苯二芳烃酯的简单合成途径。我们讨论了它采用的异常构象，并提出这是由于酯取代基的吸电子性质引起的，该酯取代基使它们比酚具有更好的氢键受体，确保它们各自仅充当供体。密度泛函理论（DFT）计算表明，这种构象的出现是由于该化合物的异常构型异构现象和原型氢键被酯官能团打断的结果。我们讨论了它采用的异常构象，并提出这是由于酯取代基的吸电子性质引起的，该酯取代基使它们比酚具有更好的氢键受体，确保它们各自仅充当供体。密度泛函理论（DFT）计算表明，这种构象的出现是由于该化合物的异常构型异构现象和原型氢键被酯官能团打断的结果。我们讨论了它采用的异常构象，并提出这是由于酯取代基的吸电子性质引起的，该酯取代基使它们比酚具有更好的氢键受体，确保它们各自仅充当供体。密度泛函理论（DFT）计算表明，这种构象的出现是由于该化合物的异常构型异构现象和原型氢键被酯官能团打断的结果。