4-水杨醛亚氨基-3-烷基-1,2,4-三唑-5-硫酮合成和晶体结构

Synthesis and crystal structure of 4-salicylideneamino-3-methyl-1, 2, 4-triazol-5-thione

合成了5个4 - 水杨醛亚氨基- 3- 烷基- 1,2 ,4 -三唑- 5 - 硫酮化合物,并用IR和1 HNMR手段对这些化合物进行了表征.通过X Ray单晶衍射方法对化合物4 -水杨醛亚氨基- 3 -甲基-1,2 ,4 -三唑- 5 - 硫酮(IIa)结构进行了测定,确定该晶体属于单斜晶系,空间群为P2 1 n ,晶胞参数a =1.2 6 97(3) ,b =0 .74 0 7(15 ) ,c =1.2 75 0 (3)nm ,β=117.6 8(3)°,V =1.0 6 185 (4) (nm) 3,Z =4 ,Dc =1.4 6 5g cm3,μ=0 .2 88mm- 1 ,F(0 0 0 ) =4 88,R =0 .0 5 8,wR =0 .16 4 .其中独立衍射点数为2 6 6 0个,2 130个为可观察衍射点(I >2σ(I) )用于结构测定和修正.结果表明所有目标产物4 -水杨醛亚氨基-3- 烷基- 1,2 ,4 - 三唑- 5 - 硫酮(IIa～c ,IIId～e)中甲亚胺(CN)构型是E构型(反式) ,并且是硫酮式互变异构体而不是硫醇式,并且化合物的所有非氢原子共平面.

Five 4-salicylideneamino-3-methyl-1,2,4-triazol-5-thiones (IIa) were synthesized and characterized by IR and 1H NMR methods. The crystal structure of 4-salicylideneamino-3-methyl-1,2,4-triazol-5-thione (IIa) (C_ 10H_ 10N_4OS, Mr=234.28) was determined by single-crystal X-ray diffraction method. It belongs to monoclinic crystal structure. The space group is P2_1/n with unit cell constants a=1.269?7(3), b=0.740?7(15), c=1.275?0(3)nm, β=1.176?8(3)°,V=1.061?85(4)(nm)3, Z=4,D_c=1.465?g/cm3,μ=0.288?mm -1, F(000)=488, and R and wR are 0.058 and 0.164 respectively for 2?660 unique reflections with 2?130 observed reflections (I>2σ(I)). The results prove that the the azomethine CN bond configuration of the title compound is E and IIa could be assigned to the thione tautomeric form rather than the thiol form. All the non-hydrogen atoms of the title compound are essentially coplanar.