邻苯二甲酰氨基酸的合成及晶体结构  

Synthesis and Crystal Structure of Phthalylamino-acids

作　　者：黄月芳[1] 张培[1] 黄林[1] 杨春龙[1] 

机构地区：[1]南京农业大学理学院,江苏南京210095

出　　处：《精细化工》2008年第7期664-667,680,共5页Fine Chemicals

基　　金：江苏省自然科学基金资助项目(BK2005094)~~

摘　　要：用邻苯二甲酸酐作氨基保护剂,与6种氨基酸缩合制备了邻苯二甲酰氨基酸。重点考察了邻苯二甲酰甘氨酸的合成条件对产物收率的影响,最佳合成条件为:反应温度140℃,反应时间30 min,n(甘氨酸)∶n(邻苯二甲酸酐)=1∶1.2,收率95.6%。以同样的条件合成的另外5种邻苯二甲酰氨基酸的收率也都达到了81%以上。经解析发现,邻苯二甲酰甘氨酸一水合物的晶体结构属单斜晶系,P21/n空间群,晶胞参数:a=7.638 0(15)nm,b=13.803(3)nm,c=10.009(2)nm,β=106.67(3)°,Z=4,Dc=1.466 g.cm-3,μ=0.120 mm-1,F(000)=464。最终偏离因子R=0.060 6,wR=0.164 7。晶体结构分析表明,分子间氢键连接整个分子形成沿[010]方向的锯齿状长链,再通过π-π堆积作用形成稳定的三维立体结构。Six phthalylamino-acids were synthesized from phthalyl anhydride and amino-acids. The optimal conditions for preparing phthalyl-glycine were n （glycine） ： n （ phthalyl anhydride ） = 1 ： 1.2, reaction temperature 140℃ and reaction time 30 min. The yield can reach 95.6% , and the yields of other five phthalylamino-acids are higher than 81%. The crystal structure of phthalylglycine hydrate was determined by single crystal X-ray diffraction：the crystal belonging to monoclinic system, space group P21/n with a = 7.638 0 （ 15 ） nm, b = 13. 803 （ 3 ） nm, c = 10. 009 （ 2 ） nm ,β = 106.67 （ 3 ） °, Z = 4,Dc = 1. 466 g · cm^-3 ,μ =0. 120 mm^-1 ,F（000） =464. The final R =0. 060 6 and wR =0. 164 7. The crystal structure shows that zigzag chains running along the [010]direction are formed through the intermolecular hydrogen bonds, and further a steady three-dimensional structure is generated by π-π stacking interactions between the phthalyl rings.

关 键 词：氨基保护 邻苯二甲酸酐 甘氨酸 晶体结构 

分 类 号：TQ226.36[化学工程—有机化工]