Home

Citation: Yang Xiaoli, Xie Zongbo, Zhou Peng, Ai Feng, Le Zhanggao. Online Monitoring of Friedländer Reaction Using Extractive Electrospray Ionization Tandem Mass Spectrometry[J]. Chemistry, ;2018, 81(5): 445-449. shu

Online Monitoring of Friedländer Reaction Using Extractive Electrospray Ionization Tandem Mass Spectrometry

Yang Xiaoli ² ,
Xie Zongbo ^1,2,, ,
Zhou Peng ¹ ,
Ai Feng ² ,
Le Zhanggao ^1,2,,

1.
Jiangxi 2011 Joint Center for the Innovative Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013
2.
Department of Applied Chemistry, East China University of Technology, Nanchang 330013

Corresponding author: Xie Zongbo, zbxie@ecit.cn Le Zhanggao, zhgle@ecit.edu.cn
Received Date: 10 July 2017
Accepted Date: 18 March 2018

Figures(8)

Mass Spectrometry online monitoring of organic chemical reaction can capture the signal and change of the reactants, intermediates, and products in the reaction process in real time so as to deepen the understanding of the nature of the reaction. In this study, extractive electrospray ionization tandem mass spectrometry (EESI-MS) were used to monitor Friedlander condensation reaction of 2-aminoacetophenone and acetylacetone using oxalate as a catalyst. At different time of the reaction, the molecular ion peak of reactants (m/z 136), intermediates (m/z 236, m/z 218) and product (m/z 200) signal were captured, the changes of them in the course of the reaction with time trends were recorded, the reaction mechanism was deduced.
- EESI-MS,
- Online monitoring,
- Reaction mechanism,
- Friedländer condensation reaction
1. [1]
2. [2]
3. [3]
4. [4]
  G A Ramann, B J Cowen. Tetrahed. Lett., 2015, 56(46):6436~6439.
5. [5]
  F Tufail, M Saquib, S Singh et al. New J. Chem., 2017, 41(4):1618~1624.
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
  A Watanabe, C Watanabe, R R Freeman et al. Anal. Chem., 2016, 88(10):5462~5468.
12. [12]
13. [13]
  M Behrends, J Sävmarker, P J R Sjöberg et al. ACS Catal., 2011, 1(1):1455~1459.
14. [14]
15. [15]
  Y Zhou, Y Wu, M Yao et al. Anal. Chem., 2016, 88(24):12060~12065.
16. [16]
  S Fürmeier, J O Metzger. J. Am. Chem. Soc., 2004, 126(44):14485~14492.
17. [17]
  N Shankaraiah, N Markandeya, V Srinivasulu et al. J. Org. Chem., 2011, 76(17):7017~7026.
18. [18]
  H G O Alvim, G A Bataglion, L M Ramos et al. Tetrahedron, 2014, 70(20):3306~3313.
19. [19]
  P J Gallimore, M Kalberer. Environ. Sci. Technol., 2013, 47(13):7324~7331.
20. [20]
  H Chen, B Hu, Y Hu et al. J. Am. Soc. Mass Spectr., 2009, 20(4):719~722.
21. [21]
  L Zhu, G Gamez, H W Chen et al. Rapid Commun. Mass Spectr., 2008, 22(19):2993~2998.
22. [22]
23. [23]
  M Dabiri, M Baghbanzadeh, M S Nikcheh. Monats. Chem., 2007, 138(12):1249~1252.
24. [24]
  J Marco-Contelles, E Pérez-Mayoral, A Samadi et al. Chem. Rev., 2009, 109(6):2652~2671.
1. [1]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
2. [2]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
3. [3]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
4. [4]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
5. [5]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
6. [6]
  Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
7. [7]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
8. [8]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
9. [9]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
10. [10]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
11. [11]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
12. [12]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . Sulfide Solid Electrolyte Synthesized by Liquid Phase Approach and Application in All-Solid-State Lithium Batteries. Acta Physico-Chimica Sinica, 2025, 41(1): 100004-0. doi: 10.3866/PKU.WHXB202309019
13. [13]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
14. [14]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
15. [15]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
16. [16]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
17. [17]
  Lancanghong Chen , Xingtai Yu , Tianlei Zhao , Qizhi Yao . Exploration of Abnormal Phenomena in Iodometric Copper Quantitation Experiment. University Chemistry, 2025, 40(7): 315-320. doi: 10.12461/PKU.DXHX202408089
18. [18]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
19. [19]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
20. [20]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(1414)
HTML views(167)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return