HYDROGEN-BOND DIRECTED COCRYSTALLIZATION AND MOLECULAR RECOGNITION PROPERTIES OF DIARYLUREAS
HYDROGEN-BOND DIRECTED COCRYSTALLIZATION AND MOLECULAR RECOGNITION PROPERTIES OF DIARYLUREAS
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DOI：
10.1021/ja00179a028
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发表时间：
1990-11-07
影响因子：
15
通讯作者：
PANUNTO, TW
中科院分区：
文献类型：
--
作者：
ETTER, MC;URBANCZYKLIPKOWSKA, Z;PANUNTO, TW
采用共结晶方法研究了一系列二酰脲（DAU）化合物的氢键定向分子识别特性，探讨了宿主分子和客体分子的氢键给体和受体选择性。芳基环上具有间位取代吸电子基团的二芳脲类化合物能够与多种氢键受体形成共晶配合物。一种特殊的DAU， 1,3 -二（间硝基苯基）尿素，主要作为质子供体，是已知具有这种性质的少数有机分子之一。它的氢键接受能力急剧降低，可能是因为两个非常弱的CH™0相互作用响应于客体受体分子的存在，有效地抵消了尿素羰基强大的质子接受能力。只有含有元取代吸电子基团的DAU化合物才具有这种性质。报道了四种DAU化合物及其六种共晶结构的晶体结构。此外，还制备了其他19个DAU共晶，并通过化学和光谱学方法对其进行了表征，并根据光谱学类比对已知晶体结构的氢键模式进行了分配。从这些数据推导出二芳脲类化合物的氢键规律，用于预测相关结构中的氢键模式。
The hydrogen bond directed molecular recognition properties of a series of diarylurea (DAU) compounds have been studied using cocrystallization to probe hydrogen bond donor and acceptor selectivity of the host and guest molecules. Diarylureas with meta-substituted electron-withdrawing groups on the aryl rings are capable of forming cocrystalcomplexes with a wide variety of hydrogen bond acceptors. One particular DAU, l, 3-bis (m-nitrophenyl) urea, behaves primarily as a proton donor, one of the few organic molecules known to have this property. Its hydrogen bond accepting ability is drastically reduced, possibly because of two very weak CH™ 0 interactions occurring in response to the presence of guest acceptor molecules and effectively negating the powerful proton-accepting ability of the urea carbonyl group. Only DAU compounds with meta-substituted electron-withdrawing groupshave this property. The crystal structures of four DAU compounds and six of their cocrystal structures are reported. In addition, 19 other DAU cocrystals were prepared and characterized by chemical and spectroscopic means, and their hydrogenbond patterns were assigned based on spectroscopic analogies to those with known crystal structures. From this data hydrogen bond rules for diarylureas havebeen derived for use in predicting hydrogen bond patterns in related structures.