2-[(2-氨基苯亚胺)-苯甲基]-4-氯酚的合成、晶体结构及抑菌活性

Synthesis,Crystal Structure and Antibacterial Activities of 2-[(2-Aminophenylimino)phenylmethyl]-4-chlorophenol

以苯甲酰氯和对氯苯酚为原料,经过酯化f、ries重排、缩合等一系列反应,合成了一种缩胺类单席夫碱,并通过NMRI、R、元素分析和X射线衍射进行了结构表征。该晶体属于三斜晶系,P1空间群,a=0.856 95(17)nm,b=0.942 63(19)nm,c=1.106 7(2)nm,α=69.17(3)°,β=84.90(3)°,γ=77.69(3)°,V=0.816 2(3)nm3,Z=2,Dc=1.313 4(5)g.cm-3,F(000)=336.0,μ(Mo Kα)=0.240 mm-1,最终偏差因子分别为R=0.076 6,wR=0.148 0。该化合物的晶胞中存在分子内C—H…π和O—H…N,N—H…O,N—H…N氢键两种相互作用力,这些作用力使得晶体结构趋于稳定。利用单片纸碟法对该配体的抑菌活性进行了研究,选用2种细菌(E.coli,S.aureus)和1种真菌(C.albi-cans)作为供试菌种,结果表明配体对3种菌种的生长均有一定的抑制作用。

The mono-condensed Schiff base （C19 H15 C1N2 O, Mr= 322.78） was obtained by esterification, fries rearrangement and condensation using benzoyl chloride and p- bromophenole as the raw materials. Then the tilted compound was characterized by NMR, IR, elemental analysis and X-ray single-crystal diffraction. The tilted compound crystallized in the triclinic system, space group P 1- with a=0.856 95（17）nm,b=0.942 63（19）nm,c=1.106 7（2）nm,α=69.17（3）°,β=84.90（3）°,γ=77.69（3）°,V=0.816 2（3）nm3,Z=2,Dc=1.313 4（5）g.cm-3,F（000）=336.0,μ（Mo Kα）=0.240 mm-1, the final R=0. 076 6 and wR=O. 148 0. The molecular structure was stabilized by intramolecular C--H…π and O--H…N, N--H…O, N--H…N inter- and intra-molecular hydrogen-bond interactions. The antibacterial activity of tilted compound was carried out using the paper disc method. The results showed that the tilted compound can inhibit the growth of two bacteria （E. coli, S. aureus） and a fungus（C, albicans）.