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首页> 外文期刊>RSC Advances >Preferential N–H?:C [[double bond splayed right]] hydrogen bonding involving ditopic NH-containing systems and N-heterocyclic carbenes
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Preferential N–H?:C [[double bond splayed right]] hydrogen bonding involving ditopic NH-containing systems and N-heterocyclic carbenes

机译：优选N-H？：C [[双键展开右]]致含DIToPIC NH的体系和N-杂环碳的氢键

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摘要

Hydrogen bonding plays a critical role in maintaining order and structure in complex biological and synthetic systems. N -heterocyclic carbenes (NHCs) represent one of the most versatile tools in the synthetic chemistry toolbox, yet their potential as neutral carbon hydrogen bond acceptors remains underexplored. This report investigates this capability in a strategic manner, wherein carbene-based hydrogen bonding can be assessed by use of ditopic NH -containing molecules. N–H bonds are unique as there are three established reaction modes with carbenes: non-traditional hydrogen bonding adducts (X–H?:C), salts arising from proton transfer ([H–C] ~(+) [X] ~(?) ), or amines from insertion of the carbene into the N–H bond. Yet, there are no established rules to predict product distributions or the strength of these associations. Here we seek to correlate the hydrogen bond strength of symmetric and asymmetric ditopic secondary amines with 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene ( IPr , a representative NHC). In symmetric and asymmetric ditopic amine adducts both the solid-state (hydrogen bond lengths, NHC interior angles) and solution-state ( ~(1) H Δ δ of NH signals, ~(13) C signals of carbenic carbon) can be related to the p K _(a) of the parent amine.
机译：氢键在维持复杂生物和合成系统中的顺序和结构中起着关键作用。 n - 汉腔环Clbenes（NHC）代表合成化学工具箱中最通用的工具之一，但它们作为中性碳氢粘合受体的潜力仍未缺乏缺陷。该报告以战略方式研究了该能力，其中基于卡内的氢键可以通过使用DITopic NH - 甲型分子来评估。 N-H键是独一无二的，因为有三种既定的反应模式与碳酸盐：非传统氢键合物（X-H？：C），由质子转移产生的盐（[H-C]〜（+）[x]〜 （α）），或从插入切菜进入N-H键的胺。然而，没有建立的规则来预测产品分布或这些关联的实力。在这里，我们寻求将对称和不对称二次二胺的氢键强度与1,3-双（2,6-二异丙基苯基）咪唑-2- ylidene（IPR，代表性NHC）相关联。在对称和不对称的ditopic胺加合物加合固态（氢键长度，NHC内部角度）和溶液 - 状态（〜（1）HΔδ的NH信号，碳碳的〜（13）C信号）可以是相关的到母胺的p k _（a）。

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