Synthesis of Thiosemicarbazones and Their Organoiodine Cocrystals: Cooperative Effects of Halogen and Hydrogen Bonding
Synthesis of Thiosemicarbazones and Their Organoiodine Cocrystals: Cooperative Effects of Halogen and Hydrogen Bonding
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缩氨基硫脲及其有机碘共晶的合成：卤素和氢键的协同作用
DOI：
10.1007/s10870-022-00931-7
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发表时间：
2022
影响因子：
0.8
通讯作者：
Pennington, William T.
中科院分区：
文献类型：
--
作者：
Peloquin, Andrew J.;Ragusa, Arianna C.;Arman, Hadi D.;McMillen, Colin D.;Pennington, William T.
利用氨基硫脲与丙酮或醛的简单加成-消除反应，合成了9个缩氨基硫脲。选择含有额外杂原子的醛，以增加可能的分子间相互作用的多样性。此外，缩氨基硫脲的合成是以常见的卤键给体1，2-，1，3-或1，4-二碘四氟苯、1，3，5-三氟-2，4，6-三碘苯或四碘乙烯为原料进行的。这些反应导致了12个新的显示卤素成键的共晶的表征。两个缩氨基硫脲单元通过一对N-H···S氢键进行二聚化是该系列固体结构的普遍特征，氢键网络经常将这些基序延伸成链。有机碘通过I···S或I···N卤键，或不常见的S···I硫键将链连接起来。利用缩氨基硫脲与丙酮或醛的简单加成-消除反应，合成了9个缩氨基硫脲，其中7个与常见的卤键供体形成了共晶。实验中观察到明显的N-H···S氢键，其中S···i卤键和硫键促进了共晶中的长程堆积。
Utilizing the facile addition–elimination reaction of thiosemicarbazide with acetone or aldehydes, nine thiosemicarbazones were synthesized. Aldehydes were chosen which contain additional heteroatoms to increase the diversity of possible intermolecular interactions. Further, the thiosemicarbazone synthesis was conducted in situ with one of the common halogen bond donors 1,2-, 1,3-, or 1,4-diiodotetrafluorobenzene, 1,3,5-trifluoro-2,4,6-triiodobenzene, or tetraiodoethylene. These reactions resulted in the characterization of 12 new cocrystals showcasing halogen bonding. The dimerization of two thiosemicarbazone units through a pair of N‒H···S hydrogen bonds was a universal feature of the solid-state structures in this series, with the hydrogen bond network often extending these motifs into chains. The organoiodines serve to link chains through either I···S or I···N halogen bonding, or less commonly, S···I chalcogen bonding. This variety of intermolecular interactions leads to the formation of double-stranded chains, ribbons, and sheets.Graphical AbstractUtilizing the facile addition–elimination reaction of thiosemicarbazide with acetone or aldehydes, nine thiosemicarbazones were synthesized, seven of which were isolated as cocrystals with common halogen bond donors. Significant N–H···S hydrogen bonding was observed in all, with S···I halogen and chalcogen bonding contributing to the long-range packing in the cocrystals.
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