Citation: WANG Xiao-Wei, JIANG Gang, DU Ji-Guang. Structures, Infrared Spectra and Reactivities of (+)-Catechin Metal Complexes[J]. Acta Physico-Chimica Sinica, ;2011, 27(02): 309-314. doi: 10.3866/PKU.WHXB20110202 shu

Structures, Infrared Spectra and Reactivities of (+)-Catechin Metal Complexes

1.
Institute of Atomic and Molecular Physics, Sichuan University, Chengdu 610065, P. R. China

Received Date: 12 October 2010
Available Online: 15 December 2010

We investigated the structures, infrared spectra, and reactivities of (+)-catechin (Cc, C₁₅H₁₄O₆) and its metal complexes (M-Cc, M=Ca, Zn, Cd, Cu, Al, Cr) using density functional theory (DFT) with the B3LYP functional and the 6-311+G(d,p) basis set for non-metallic elements and the LANL2DZ basis set for metals. The results showed that the M-Cc complexes were structurally and spectroscopically different from their precursor (Cc). The frontier molecular orbitals and conceptual density functional theory descriptors imply that some of the M-Cc systems tend to be more active than the Cc monomer. Different metal complexes were found to have different values for the indices. These results are helpful in understanding the studied properties of (+)-catechin and other metallic compounds.
- (+)-Catechin,
- Metal complex,
- Reactivity,
- Conceptual density functional theory,
- Infrared spectrum
1. [1]
  
  (1) Hoshino, N.; Kimura, T.; Hayakawa, F.; Yamaji, A.; Ando, T. J. Lett. Appl. Microbiol. 2000, 31, 213.
2. [2]
  (2) Kumamoto, M.; Sonda, T.; Nagayama, K.; Tabata, M. Biosci. Biotechnol. Biochem. 2001, 65, 126.
3. [3]
  (3) Za , M. P.; Oteiza, P. I. Free Radic. Biol. Med. 2001, 31, 266.
4. [4]
  (4) Sun, S. L.; He, G. Q.; Yu, H. N.; Yang, J. G.; Borthakur, D.; hang, L. C.; Shen, S. R.; Das, U. N. Mol. Nutr. Food Res. 2008, 52, 465.
5. [5]
  (5) Sun, S. L.; Yu, H. N.; Ling, C. J.; Shen, S. R.; Miao, A. Q.; Pan, S. S.; Zhao, C. Y. Chin. J. Agric. Biotechnol. 2009, 17, 902. 孙世利, 于海宁, 凌彩金, 沈生荣, 苗爱清, 潘顺顺, 赵超艺. 业生物技术学报, 2009, 17, 902.]
6. [6]
  (6) Hu, C.; Kitts, D. D. Mol. Cell. Biochem. 2001, 218, 147.
7. [7]
  (7) Navarro, R. E.; Santacruz, H.; Inoue, M. J. Inorg. Biochem. 2005, 99, 584.
8. [8]
  (8) Tang, D. S.; Shen, S. R.; Chen, X.; Zhang, Y. Y.; Xu, C. Y. J. Zhejiang Univ. Sci. 2004, 5, 668.
9. [9]
  (9) Mattice,W. L.; Tobiason, F. L.; Houglum, K.; Shanafelt, A. J. Am. Chem. Soc. 1982, 104, 3359.
10. [10]
  (10) Esparza, I.; Salinas, I.; Santamar, C.; Garc-Mina, J. M.; ernandez, J. M. Anal. Chim. Acta. 2005, 543, 267.
11. [11]
  (11) Chen, H.; Shan, Z. H. China Leather 2008, 37, 20.
12. [12]
  [陈慧, 志华. 中国皮革, 2008, 37, 20.]
13. [13]
  (12) (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. (c) Lee, C.; Yang,W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
14. [14]
  (13) Andersson, M. P.; Uvdal, P. J. Phys. Chem. A 2005, 109, 2937.
15. [15]
  (14) Liu, S. B.; Langenaeker,W. Theor. Chem. Acc. 2003, 110, 338.
16. [16]
  (15) (a) Parr, R. G.; Yang,W. Density Functional Theory of Atoms nd Molecules; Oxford University Press: New York, 1989. (b) Geerlings, P.; De Proft, F.; Langenaeker,W. Chem. Rev. 2003, 103, 1793.
17. [17]
  (16) (a) Rong, C. Y.; Lian, S. X.; Yin, D. L.; Zhong, A. G.; Zhang, R. Q.; Liu, S. B. Chem. Phys. Lett. 2007, 434, 149. (b) Xia, Y.; Yin, D. L.; Rong, C. Y.; Xu, Q.; Yin, D. H.; Liu, S. B. J. Phys. Chem. A 2008, 112, 9970.
18. [18]
  (17) (a) Parr, R. G.; Szentpaly, L. V.; Liu, S. B. J. Am. Chem. Soc. 1999, 105, 1922. (b) Liu, S. B.; Parr, R. G. J. Chem. Phys. 1997, 106, 5578.
19. [19]
  (18) Mulliken, R. S. J. Chem. Phys. 1934, 2, 782.
20. [20]
  (19) Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533.
21. [21]
  (20) Liu, S. B. Acta Phys. -Chim. Sin. 2009, 25, 590.
22. [22]
  [刘述斌. 物理学学报, 2009, 25, 590.]
23. [23]
  (21) Parr, R. G.; Yang,W. J. Am. Chem. Soc. 1984, 106, 4049.
24. [24]
  (22) Ayers, P.W.; Levy, M. Theor. Chem. Acc. 2000, 103, 353.
25. [25]
  (23) (a) Ayers, P.W.; Yang,W.; Bartolotti, L. The Fukui Function. In Chemical Reactivity Theory: a Density Functional Theory View; hattaraj, P. K. Ed.; Taylor & Francis Group: London, 2009. (b) Yang, W. T.; Parr, R. G.; Pucci, R. J. Chem. Phys. 1984, 81, 862. (c) Ayers, P.W. Theor. Chem. Acc. 2001, 106, 271. (d) Senet, P. J. Chem. Phys. 1997, 107, 2516.
26. [26]
  (24) Morell, C.; Grand, A.; Toro-Labbe, A. J. Phys. Chem. A 2005, 09, 205.
27. [27]
  (25) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, evision D.02; Gaussian, Inc.: Pittsburgh, PA, 2003.
28. [28]
  (26) Le Nest, G.; Caille, O.;Woudstra, M.; Roche, S.; Burlat, B.; elle, V.; Guigliarelli, B.; Lexa, D. Inorg. Chim. Acta. 2004, 57, 2027.
29. [29]
  (27) Einstein, F.W. B.; Kiehlmann, E.;Wolowidnyk, E. K. Can. J. Chem. 1985, 63, 2176.
30. [30]
  (28) Bakhtiyor, F. R.; Nasrulla, D. A.; Vladimir, N. S. QSAR Comb. Sci. 2005, 24, 1056.
31. [31]
  (29) Georgiev, A.; Karamanchev, I.; Dimov, D.; Zhivkov, I.; passova, E. J. Mol. Struct. 2008, 888, 214.
32. [32]
  (30) Peng, L. L.; Liu, J. L.; Guo, Y.; Xue, Y. Chemical Research and pplication 2008, 20, 1001.
33. [33]
  [彭黎黎, 刘靖丽, 郭勇, 英. 化学研究与应用, 2008, 20, 1001.]
34. [34]
  (31) Ramos-Tejada, M. M.; Duran, J. D. G.; Ontiveros-Ortega, A.; spinosa-Jimenez, M.; Perea-Carpio, R.; Chibowski, E. Colloids Surf. B 2002, 24, 297.
35. [35]
  (32) Yang, S. Z. Theory of Organic Structure; Hefei University of echnology Press: Hefei, 2003; pp 58-64.
36. [36]
  [杨善中. 有机结构论. 合肥: 合肥工业大学出版社, 2003: 58-64.]
37. [37]
  (33) Zheng, K. C.; Huang, J. D.; Sheng, Y.; Zhang, S. Y. Chin. J. Inorg. Chem. 1999, 15, 74.
38. [38]
  [郑康成, 黄加多, 沈勇, 张水勇. 无机化学学报, 1999, 15, 74.]
39. [39]
  (34) Li, X. F.;Wang, X. Y.; Liu,W. Q.; Tan, Y. Q.; Li, J. J. Computers and Applied Chemistry 2005, 22, 287.
40. [40]
  [李新芳, 学业, 刘万强, 谭援强, 李建军. 计算机与应用化学, 2005, 2, 287.]
41. [41]
  (35) Zhong, A. G.;Wu, J. Y.; Yan, H.; Jin, Y. X.; Dai, G. L.; Jiang, H. J.; Pan, F. Y.; Liu, S. B. Acta Phys. -Chim. Sin. 2009, 25, 1367. 钟爱国, 吴俊勇, 闫华, 金燕仙, 戴国梁, 蒋华江, 潘富友, 述斌. 物理化学学报, 2009, 25, 1367.]
42. [42]
  (36) Zhong, A. G.; Haung, L.; Li, B. L.; Jiang, H. J.; Liu, S. B. Acta hys. -Chim. Sin. 2010, 26, 2763.
43. [43]
  [钟爱国, 黄凌, 李佰林, 华江, 刘述斌. 物理化学学报, 2010, 26, 2763.]
1. [1]
  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
2. [2]
  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
3. [3]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
4. [4]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
5. [5]
  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
6. [6]
  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
7. [7]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
8. [8]
  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
9. [9]
  Yiying Yang , Dongju Zhang . Elucidating the Concepts of Thermodynamic Control and Kinetic Control in Chemical Reactions through Theoretical Chemistry Calculations: A Computational Chemistry Experiment on the Diels-Alder Reaction. University Chemistry, 2024, 39(3): 327-335. doi: 10.3866/PKU.DXHX202309074
10. [10]
  Zuozhong Liang , Lingling Wei , Yiwen Cao , Yunhan Wei , Haimei Shi , Haoquan Zheng , Shengli Gao . Exploring the Development of Undergraduate Scientific Research Ability in Basic Course Instruction: A Case Study of Alkali and Alkaline Earth Metal Complexes in Inorganic Chemistry. University Chemistry, 2024, 39(7): 247-263. doi: 10.3866/PKU.DXHX202310103
11. [11]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
12. [12]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
13. [13]
  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
14. [14]
  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
15. [15]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
16. [16]
  Wei Li , Ze Chang , Meihui Yu , Ying Zhang . Curriculum Ideological and Political Design of Piezoelectricity Measurement Experiments of Coordination Compounds. University Chemistry, 2024, 39(2): 77-82. doi: 10.3866/PKU.DXHX202308004
17. [17]
  Ji Qi , Jianan Zhu , Yanxu Zhang , Jiahao Yang , Chunting Zhang . Visible Color Change of Copper (II) Complexes in Reversible SCSC Transformation: The Effect of Structure on Color. University Chemistry, 2024, 39(3): 43-57. doi: 10.3866/PKU.DXHX202307050
18. [18]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
19. [19]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
20. [20]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431

Get Citation

PDF

XML

Metrics

PDF Downloads(1631)
Abstract views(3341)
HTML views(35)

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