Competition between chalcogen and halogen bonding assessed through isostructural species
Competition between chalcogen and halogen bonding assessed through isostructural species
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通过同构物种评估硫属元素和卤素键之间的竞争
DOI：
10.1107/s205322962201052x
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Aakeröy, Christer B.
中科院分区：
文献类型：
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作者：
De Silva, Viraj;Magueres, Pierre Le;Averkiev, Boris B.;Aakeröy, Christer B.
2-氨基-5-（4-卤代苯基）-1,3,4-硫代二唑的氨基被溴/碘取代，得到了一个由四个组成相关的化合物组成的文库。它们是2-碘-5-（4-碘苯基）-1,3,4-噻二唑，C8H4I2N2S， 2-溴-5-（4-溴苯基）-1,3,4-硒二唑，c8h4br2se， 2-溴-5-（4-碘苯基）-1,3,4-硒二唑，C8H4BrIN2Se，和2-溴-5-（4-碘苯基）-1,3,4-噻二唑，C8H4BrIN2S。所有这些都是等结构的，并包含分叉的Ch⋯N （Ch是硫）和X⋯X （X是卤素）相互作用，形成了一个锯齿形的包装基序。硫键供体和最佳受体N原子之间的非共价Ch⋯N相互作用优先出现，而不是可能与同一N原子形成的卤素键。Hirshfeld表面分析和能量框架计算表明，总的来说，分叉的碳键比卤素键更强，在该体系中对结构的影响更大。
The amino group of 2-amino-5-(4-halophenyl)-1,3,4-chalcogenadiazole has been replaced with bromo/iodo substituents to obtain a library of four compositionally related compounds. These are 2-iodo-5-(4-iodophenyl)-1,3,4-thiadiazole, C8H4I2N2S, 2-bromo-5-(4-bromophenyl)-1,3,4-selenadiazole, C8H4Br2N2Se, 2-bromo-5-(4-iodophenyl)-1,3,4-selenadiazole, C8H4BrIN2Se, and 2-bromo-5-(4-iodophenyl)-1,3,4-thiadiazole, C8H4BrIN2S. All were isostructural and contained bifurcated Ch⋯N (Ch is chalcogen) and X⋯X (X is halogen) interactions forming a zigzag packing motif. The noncovalent Ch⋯N interaction between the chalcogen-bond donor and the best-acceptor N atom appeared preferentially instead of a possible halogen bond to the same N atom. Hirshfeld surface analysis and energy framework calculations showed that, collectively, a bifurcated chalcogen bond was stronger than halogen bonding and this is more structurally influential in this system.