高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (11): 2496-2502.doi: 10.7503/cjcu20200379

• 物理化学 • 上一篇    下一篇

SERS-HPLC联用技术对邻氨基苯硫酚与邻碘苯甲酰氯反应的监测

张辉, 张晨杰, 徐敏敏(), 袁亚仙, 姚建林()   

  1. 苏州大学材料与化学化工学部,苏州 215123
  • 收稿日期:2020-06-22 出版日期:2020-11-10 发布日期:2020-11-06
  • 通讯作者: 徐敏敏,姚建林 E-mail:xumm@suda.edu.cn;jlyao@suda.edu.cn
  • 基金资助:
    国家自然科学基金(批准号(21773166);21673152)资助

Investigation on the Reaction of o-Aminothiophenol and 2-Iodobenzoyl Chloride Monitored by SERS-HPLC Technique

ZHANG Hui, ZHANG Chenjie, XU Minmin(), YUAN Yaxian, YAO Jianlin()   

  1. College of Chemistry,Chemical Engineering and Materials Science,Soochow University,Suzhou 215123,China
  • Received:2020-06-22 Online:2020-11-10 Published:2020-11-06
  • Contact: XU Minmin,YAO Jianlin E-mail:xumm@suda.edu.cn;jlyao@suda.edu.cn
  • Supported by:
    the National Natural Science Foundation of China(21773166)

摘要:

通过表面增强拉曼光谱(SERS)与高效液相色谱(HPLC)联用开展了在线监测催化剂对邻氨基苯硫酚(OATP)与邻碘苯甲酰氯反应的影响. 结果表明, 无催化剂时反应产物为1b{S-[2-(2碘苯甲酰氨基)苯基]-2-碘代苯硫酸盐}和2b{N,N′-[二硫(2, 1-亚苯基)]二(2-碘苯甲酰胺)}, 在醋酸铜催化下生成3b{10-(2-碘苯甲酰基)二苯并[b, f ][1, 4]硫氮杂-11(10H)-酮}; 无催化剂条件下经历亲核取代反应及硫自由基耦合的过程, 在醋酸铜催化下产物 1b 的结构发生变异生成3b. 所得结果与核磁质谱等常规非现场技术解析结构一致.

关键词: 表面增强拉曼光谱, 高效液相色谱, 联用技术, 邻氨基苯硫酚, 邻碘苯甲酰氯

Abstract:

Surface enhanced Raman spectroscopy(SERS) has been employed in the structural characterization successfully due to its ultra-high sensitivity. However, it is still remained the significant challenge in the precise interpretation of spectral features for detecting multi-species systems. High performance liquid chromatography(HPLC) has been one of the most efficient techniques for the separation and detection of mixture systems, while the performance of structure analysis is highly desired. Herein, combination of SERS and HPLC can make individual advantages of high sensitivity of SERS and high efficiency in separation of HPLC together. It was extended to on-line monitor catalyst effect on the reaction of o-aminothiophenol(OATP) and 2-iodobenzoyl chloride. It was revealed that two different products were dominated in the absence of catalyst: products 1b{S-[2-(2-iodobenzamido)phenyl] 2-iodobenzothioate} and 2b{NN′-[disulfanediylbis(2, 1-phenylene)]bis-(2-iodobenzamide)}, while product 3b{10-(2-iodobenzoyl) dibenzo[b,f][1,4] thiazepin-11(10H)-one} was synthesized with copper acetate as catalyst. The results demonstrated that the reaction was undergone nucleophilic substitution and sulfur radical self-polymerization without catalyst, and the product 1b was undergone structural change to obtain product 3b with catalyst.

Key words: Surface enhanced Raman spectroscopy, High performance liquid chromatography, Hyphenated technology, o-Aminobenzene thiophenol, 2-Iodobenzoyl chloride

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