Supramolecular Synthons in Crystal Engineering. 3. Solid State Architecture and Synthon Robustness in Some 2,3-Dicyano-5,6-dichloro-1,4-dialkoxybenzenes1
Supramolecular Synthons in Crystal Engineering. 3. Solid State Architecture and Synthon Robustness in Some 2,3-Dicyano-5,6-dichloro-1,4-dialkoxybenzenes1
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晶体工程中的超分子合成子。
DOI：
10.1021/ja953372u
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发表时间：
1996
影响因子：
15
通讯作者：
G. Desiraju
中科院分区：
文献类型：
--
作者：
D. S. Reddy;Y. E. Ovchinnikov;O. Shishkin;Y. Struchkov;G. Desiraju
晶体中的超分子电子是通过分子间相互作用形成的结构单元。有机晶体的组装并不只是几何上的相互连接，而且往往是相邻双光子之间相互妥协或相互干扰的结果。因此，合成子干扰可能是系统晶体工程中的主要问题，特别是如果它导致分子和晶体结构之间缺乏对应性。相反，合成子的稳健性或耐受干扰的能力是晶体结构设计中的基本属性。这些想法是说明与一系列的1，4-二取代的2，3-二氰基-5，6-二氯苯和相关化合物的结构化学。该结构族中的超分子电子是通过极化诱导的C <$N···Cl相互作用而构建的。合成子的干扰进行了分析，一方面，疏水性和CH···N的相互作用，另一方面，这些相互作用之间的权衡。这些C N···Cl离子和其他含有较强氢键相互作用的离子之间的拓扑关系导致了化合物晶体结构中形成的网络的相似性，而这些网络在分子水平上是截然不同的。
Supramolecular synthons in crystals are structural units formed with intermolecular interactions. The assembly of an organic crystal is not just a geometrical interlinking with synthons but is often the consequence of compromise or mutual interference between adjacent synthons. Accordingly, synthon interference can be a major problem in systematic crystal engineering especially if it results in a lack of correspondence between molecular and crystal structures. Conversely, synthon robustness or the capacity to withstand interference is an essential attribute in crystal structure design. These ideas are illustrated with reference to the structural chemistry of a series of 1,4-disubstituted 2,3-dicyano-5,6-dichlorobenzenes and related compounds. The supramolecular synthons in this structural family are constructed with polarization-induced C ≡ N···Cl interactions. Synthon interference is analyzed in terms of the trade-off between these interactions on the one hand and hydrophobic and CH···N interactions on the other. Topological relationships between these C ≡ N···Cl synthons and others containing stronger hydrogen bond interactions lead to similarities in the networks formed in the crystal structures of compounds, which at the molecular level, are widely disparate.