Citation: Zhang Wenlong, Chen Dongmei, Liu Xingli, Huang Chao, Zhu Bixue. Synthesis, Structure and Anion Recognition of Urea-Functionalized Schiff Base Macrocyclic Compound[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 474-479. doi: 10.6023/cjoc201605042 shu

Synthesis, Structure and Anion Recognition of Urea-Functionalized Schiff Base Macrocyclic Compound

Key Laboratory of Macrocyclic and Supramolecular Chemistry, Guizhou University, Guiyang 550025

Corresponding author: Zhu Bixue, bxzhu@gzu.edu.cn
Received Date: 28 May 2016
Revised Date: 2 September 2016

Fund Project: the National Natural Science Foundation of China 21061003the 'Chun-Hui' Fund of Ministry of Education Z2012054

Figures(7)

A novel [1+1] Schiff base macrocyclic compound 3 has been synthesized from the reaction of precursors 1, 3-bis (3-amino-phenyl)-urea (1) with 1, 3-bis (2-formylphenoxy)-2-propa-nol (2). The macrocycle 3 was characterized by ¹H NMR, FT-IR, FABMS spectra and elemental analysis, and the crystal structure of 3 was determined by X-ray diffraction analy-sis. The results show that the macrocycle 3 displays a selective recognition ability for AcO^- ion by the coordination reaction of 3 with a series of anions using UV-vis absorption spectra technique. Furthermore, the coordination reaction of 3 with AcO^- ion was investigated via UV-Vis spectra, ¹H NMR and the isothermal titration calorimeter (ITC) respectively. The stoichiometric ratio, the association constant (K) and the thermodynamic parameters (Δ_rH_m, Δ_rS_m and Δ_rG_m) of the coordination reaction were obtained.
- Schiff base macrocycle,
- crystal structure,
- Urea,
- AcO^-,
- recognition
1. [1]
  Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486. doi: 10.1002/1521-3773(20010202)40:3<>1.0.CO;2-A
2. [2]
  Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419. doi: 10.1021/cr010421e
3. [3]
  Li, A. F.; Wang, J. H.; Wang, F.; Jiang, Y. B. Chem. Soc. Rev. 2010, 39, 3729. doi: 10.1039/b926160p
4. [4]
  Li, C. T.; Cao, Q. Y.; Li, J. J.; Wang, Z. W.; Dai, B. N. Inorg. Chim. Acta 2016, 449, 31. doi: 10.1016/j.ica.2016.04.047
5. [5]
  Wang, Z.-C.; Dai, B.-N.; Qiu, J.-F.; Cao, Q.-Y.; Ge, J.-Z. Chin. J. Org. Chem. 2015, 35, 2383 (in Chinese). doi: 10.6023/cjoc201506021
6. [6]
  Gale, P. A. Acc. Chem. Res. 2006, 39, 465. doi: 10.1021/ar040237q
7. [7]
  Huang, Z.-B.; Liu, X.-C.; Hu, M.-H.; Lin, W.; Shi, D.-Q. Chin. J. Org. Chem. 2014, 34, 382 (in Chinese). doi: 10.6023/cjoc201307040
8. [8]
  Wenzel, M.; Hiscock, J. R.; Gale, P. A. Chem. Soc. Rev. 2012, 41, 480. doi: 10.1039/C1CS15257B
9. [9]
  Zhang, F.; Tan, Z.; Yan, B.-R.; Pan, D.-W.; Bao, X.-P. Chin. J. Org. Chem. 2014, 34, 2499 (in Chinese). doi: 10.6023/cjoc201407012
10. [10]
  Du, J.; Kang, K.; Hu, J. C.; Mao, L. J.; Yuan, L. H.; Feng, W. Chin. J. Chem. 2016, 34, 1. doi: 10.1002/cjoc.v34.1
11. [11]
  Amendola, V.; Fabbrizzi, L.; Mosca, L. Chem. Soc. Rev. 2010, 39, 3889. doi: 10.1039/b822552b
12. [12]
  Boiocchi, M.; Del, B. L.; Gómez, D. E.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. J. Am. Chem. Soc. 2004, 126, 16507. doi: 10.1021/ja045936c
13. [13]
  Jian, J.-Y.; Yan, B.-R.; Pan, D.-W.; Tan, Z.; Lv, X.-Y.; Du, H.; Bao, X.-P. Chin. J. Org. Chem. 2015, 36, 1069 (in Chinese).
14. [14]
  Chutia, R.; Dey, S. K.; Das, G. Cryst. Growth Des. 2013, 13, 883. doi: 10.1021/cg3015749
15. [15]
  Zhou, Y.; Zhang, J. F.; Yoon, J. Chem. Rev. 2014, 114, 5511. doi: 10.1021/cr400352m
16. [16]
  Srikala, P.; Tarafder, K.; Trivedi, D. R. Spectrochim. Acta, Part A 2017, 170, 29. doi: 10.1016/j.saa.2016.07.001
17. [17]
  Yan, X.-Q.; Zhuo, J.-B.; Wang, J.-C.; Xie, L.-L.; Yuan, Y.-F. Chin. J. Org. Chem. 2015, 35, 2184 (in Chinese). doi: 10.6023/cjoc201505038
18. [18]
  Özkar, S.; Ülkü, D.; Yıldırım, L. T.; Biricik, N.; Gümgüm, B. J. Mol. Struct. 2004, 688, 207.
19. [19]
  Ou, M.; Den, Y.-X.; Wang, F.-F.; Zhu, C.; Zhang, Q.-L.; Zhu, B.-X. Chin. J. Org. Chem. 2013, 33, 1798 (in Chinese). doi: 10.6023/cjoc201301062
20. [20]
  Li, Q.; Zhang, Y. Q.; Zhu, Q. J.; Xue, S. F.; Xiao. X.; Tao, Z. Chem.-Asian J. 2015, 10, 1159. doi: 10.1002/asia.v10.5
21. [21]
  Boiocchi, M.; Colasson, B.; Fabbrizzi, L.; Monti, E. Inorg. Chim. Acta 2007, 360, 1163. doi: 10.1016/j.ica.2006.08.057
22. [22]
  Khandar, A. A.; Hosseini-Yazdi, S. A. Polyhedron 2003, 22, 1481. doi: 10.1016/S0277-5387(03)00124-4
23. [23]
  Sheldrick, G. M. SHELX-97, University of Göttingen, Germany, 1997.
1. [1]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
2. [2]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
3. [3]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
4. [4]
  Yan Liu , Yuexiang Zhu , Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084
5. [5]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
6. [6]
  Weina Wang , Fengyi Liu , Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029
7. [7]
  Junqiao Zhuo , Xinchen Huang , Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100
8. [8]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
9. [9]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
10. [10]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
11. [11]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
12. [12]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
13. [13]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
14. [14]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
15. [15]
  Yuxin CHEN , Yanni LING , Yuqing YAO , Keyi WANG , Linna LI , Xin ZHANG , Qin WANG , Hongdao LI , Wenmin WANG . Construction, structures, and interaction with DNA of two Sm^Ⅲ₄ complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1141-1150. doi: 10.11862/CJIC.20240258
16. [16]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
17. [17]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
18. [18]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
19. [19]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
20. [20]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1368)
HTML views(217)

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