3-溴-5-氯水杨醛缩对甲基苯胺Schiff碱的合成及晶体结构研究

Synthesis and characterization of a Schiff base from 3-bromo-5-chlorosalicylaldehyde and p-toluidine

目的合成一种新的3-溴-5-氯水杨醛Schiff碱。方法以3-溴-5-氯水杨醛和对甲基苯胺为原料通过缩合反应合成了一种新的Schiff碱,并采用X-射线单晶衍射法对其结构进行了表征。结果和结论标题化合物属于三斜晶系,空间群P1,晶胞参数a=0.813 54(14)nm,b=0.868 44(17)nm,c=1.137 40(18)nm,α=76.040(2)°,β=73.562(12)°,γ=62.458(2)°,V=0.677 9(2),Dc=1.590 g/cm3,Z=2,μ=3.215 mm-1,F(000)=324,R=0.045 4,wR=0.110 0。标题化合物以C2N1为中心呈E构型,CN双键使得整个结构趋于共面,2个芳香环之间的二面角为7.9(2)°。此外,化合物中的O—H…N分子内氢键对晶体的组成、稳定和晶体的生成起了重要的作用。

Aim To synthesize a new Schiff base which is derived from 3-bromo-5-chlorosalicylal- dehyde. Methods The compound was obtained by condensation reaction with 3-bromo-5-chloro- salicylaldehyde and p-toluidine as raw materials and its structure was characterized by X-ray single crystal diffraction. Results and Conclusion The results show that the compound crystallizes in triclinic system with space group P1 , and cell parameter a=0.81354（14）nm,b=0.86844（17）nm,c=1.13740（18）nm,α=76.040（2）°,β=73.562（12）°,γ=62.458（2）°,V=0.6779（2）,Dc=1.590g/cm^3,Z=2,μ=3.215mm^-1,F（000）=324,R=0.0454,wR=0.1100 The molecule of the title compound displays an E configuration with respect to the imine C=N double bond. The C=N double bond make aromatic rings coplanar, forming a dihedral angle of 7.9 （2）°. Another, an intramolecular O-H…N hydrogen bond plays an important role in formation, stabilization and preparation of the crystal.