Synthesis and Crystal Structure of 2-(1-Naphthalenylamino)-4-thiazolidinone  

作　　者：赵华绒 王昱丹 朱婷婷 刘曼琼 孟祥武 

机构地区：[1]Department of Chemistry,Zhejiang University [2]Sundia MediTech Company Ltd

出　　处：《Chinese Journal of Structural Chemistry》2012年第7期977-980,共4页结构化学（英文）

基　　金：supported by the Natural Science Foundation of Zhejiang Province (Y4080234)

摘　　要：The compound 2-（1-naphthalenylamino）-4-thiazolidinone was synthesized by the reaction of 1-（naphthalene-1-yl）thiourea with ethyl chloroacetate in an ionic liquid, and its structure was characterized by IR, 1H NMR and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21 /c with a=10.0081（3）, b=14.5312（4）, c=7.8739（2） , β=99.425（3）°, Z=4, V=1129.64（5）3 , Dc=1.425 g/cm3 , μ=0.269 mm-1 , F（000）=504, the final R=0.0519 and wR=0.1507. X-ray analysis indicated that the five-membered ring is essentially planar in this molecule, and intermolecular hydrogen bonds N（1）-H（1）…N（2）, C（3）-H（3）…O（1）, C（4）-H（4）…O（1） and C（12）-H（12a）…O（1） were observed. π-π Stacking interactions contribute to the stability of the structure. DSC-TG analysis showed that the title compound experienced a phase change at 190 ℃ and began to decompose above 240 ℃.The compound 2-（1-naphthalenylamino）-4-thiazolidinone was synthesized by the reaction of 1-（naphthalene-1-yl）thiourea with ethyl chloroacetate in an ionic liquid, and its structure was characterized by IR, 1H NMR and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21 /c with a=10.0081（3）, b=14.5312（4）, c=7.8739（2） , β=99.425（3）°, Z=4, V=1129.64（5）3 , Dc=1.425 g/cm3 , μ=0.269 mm-1 , F（000）=504, the final R=0.0519 and wR=0.1507. X-ray analysis indicated that the five-membered ring is essentially planar in this molecule, and intermolecular hydrogen bonds N（1）-H（1）…N（2）, C（3）-H（3）…O（1）, C（4）-H（4）…O（1） and C（12）-H（12a）…O（1） were observed. π-π Stacking interactions contribute to the stability of the structure. DSC-TG analysis showed that the title compound experienced a phase change at 190 ℃ and began to decompose above 240 ℃.

关 键 词：crystal structure ionic liquid 4-THIAZOLIDINONE X-ray diffraction thermal analysis 

分 类 号：O626[理学—有机化学]