Citation: XU Hui-Ying, WANG Wei. Interaction between Mg-Porphyrin and Nitrogen, Oxygen Heterocyclic Compounds[J]. Acta Physico-Chimica Sinica, ;2011, 27(11): 2565-2570. doi: 10.3866/PKU.WHXB20111127 shu

Interaction between Mg-Porphyrin and Nitrogen, Oxygen Heterocyclic Compounds

XU Hui-Ying ^1, ,
WANG Wei ²

1.
1. College of Biology & Environment Engineering, Zhejiang Shuren University, Hangzhou 310015, P. R. China;
2. Zhenhai Environmental Monitoring Station, Ningbo 315200, Zhejiang Province, P. R. China

Received Date: 4 July 2011
Available Online: 15 September 2011
Fund Project: 浙江省教育厅科研项目(Y200803060)资助 (Y200803060)

The interaction between nitrogen-oxygen heterocyclic compounds and a host (magnesium porphyrin) was investigated. The results showed that the magnesium atoms in the magnesium porphyrin and porphin ring were not coplanar and at a smaller dihedral angle the extent of its non-coplanar nature increased. Natural bond orbital (NBO) analysis indicated that the interaction between the lone pair of electrons on the nitrogen and oxygen atoms and the unoccupied lone pair orbital of magnesium contributes significantly to the stability of the complexes. The reduced density gradient (RDG) isosurface map and the scatter diagram indicated the location and intensity of the axial coordination interactions and the surrounding hydrogen bonding interactions. The conceptual density functional theory (DFT) parameter indicated that the complex compounds are less thermodynamically stable than magnesium porphyrin, however, they have higher reactivity. Aromatic calculations revealed that the interaction between the oxygen-containing heterocycles and the host compound made the porphin ring in the complexes anti-aromatic while the interaction between the nitrogen-containing heterocyclic and the host made the porphin ring in the complexes regionally aromatic.
- Magnesium porphyrin,
- RDG iso-surface map,
- Coordination interaction,
- Natural bond orbital,
- Aromaticity
1. [1]
  (1) Yamamoto, Y.; Hirata, Y.; Kodama, M.; Yamaguchi, T.; Matsukawa, S.; Akiba, K.; Hashizume, D.; Lwasaki, F.; Muranaka, A.; Uchiyama, M.; Chen, P.; Kadish, K. M.; Kobayashi, N. J. Am. Chem. Soc. 2010, 132, 12627.
2. [2]
  (2) Mandoj, F.; Nardis, S.; Pomarico, G.; Stefanelli, M.; Schiaffino, L.; Ercolani, G.; Prodi, L.; Genovese, D.; Zaccheroni, N.; Fronczek, F. R.; Smith, K. M.; Xiao, X.; Shen, J.; Kadish, K. M.; Paolesse, R. Inorg. Chem. 2009, 48, 10346.
3. [3]
  (3) Marques, H. M.; Brown, K. L. Coord. Chem. Rev. 2002, 225, 123.
4. [4]
  (4) Satake, A.; Kobuke, Y. Teteahedron 2005, 61, 13.
5. [5]
  (5) Yang, Z.W.; Yang, J.; Huang, X. J.; Tang, N.;Wu, B. Progress in Chemistry 2009, 21, 588. [杨再文, 杨进, 黄晓卷, 唐宁, 吴彪. 化学进展, 2009, 21, 588.]
6. [6]
  (6) Minaev, B.; Ågren, H. J. Chem. Phys. 2005, 315, 215.
7. [7]
  (7) De Souza, L. A.; Da Silva, A. M., Jr.; Junqueira, G. M. A.; Carvalho, A. C. M.; Dos Santos, H. F. J. Mol. Struc. -Theochem 2010, 959, 92.
8. [8]
  (8) Leray, I.; Vernières, M. C.; Bied-Charreton, C. Sensors and Actuators B 1999, 54, 243.
9. [9]
  (9) Charvátová, J.; Kasicka, V.; Barth, T.; Deyl, Z.; Miksík, I.; Král, V. J. Chromatography A 2003, 1009, 73.
10. [10]
  (10) Sobolewski, A. I.; Domcke,W. Chem. Phys. Lett. 2009, 479, 144.
11. [11]
  (11) Zhang, P. Y.; Zhang, J. B.; Yu, X. C.; Zhang, L.W.;Wei, X. H. Acta Phys. -Chim. Sin. 2008, 24, 143. [张鹏燕, 张建斌, 于熙昌, 张凌伟, 魏雄辉. 物理化学学报, 2008, 24, 143.]
12. [12]
  (12) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, Revision; Gaussian Inc.:Wallingford, CT, 2003.
13. [13]
  (13) Borrelli, R.; Domcke,W. Chem. Phys. Lett. 2010, 498, 230.
14. [14]
  (14) Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
15. [15]
  (15) Tian, L. Multiwfn Program, Version 2.0; http://multiwfn.codeplex.com.
16. [16]
  (16) Zheng, X. Y.;Wang, X. Y.; Yi, S. F.;Wang, N. Q.; Peng, Y. M. J. Comput. Chem. 2010, 31, 1458.
17. [17]
  (17) Johnson, E. R.; Keinan, S.; Mori-Sánchez, P.; Contreras-García, J.; Cohen, A. J.; Yang,W. T. J. Am. Chem. Soc. 2010, 132, 6498.
18. [18]
  (18) Xu, L.; Sang, P.; Zou, J.W.; Xu, M. B.; Li, X. M.; Yu, Q. S. Chem. Phys. Lett. 2011, 509, 175.
19. [19]
  (19) Liu, S. B. Acta Phys. -Chim. Sin. 2009, 25, 590. [刘述斌. 物理化学学报, 2009, 25, 590.]
20. [20]
  (20) Liu, S. B.; vind, N. J. Phys. Chem. A 2008, 112, 6690.
21. [21]
  (21) Xu, X.; Shang, Z.;Wang, G.; Li, R.; Cai, Z.; Zhao, X. J. Phys. Chem. A 2005, 109, 3754.
22. [22]
  (22) Zhong, A. G.; Huang, L.; Li, B. L.; Jiang, H. J.; Liu, S. B. Acta Phys. -Chim. Sin. 2010, 26, 2763. [钟爱国, 黄凌, 李佰林, 蒋华江, 刘述斌. 物理化学学报, 2010, 26, 2763.]
23. [23]
  (23) Wang, J. J. Chin . J. Org. Chem. 2005, 25, 1353. [王进军. 有机化学, 2005, 25, 1353.]
24. [24]
  (24) Schleyer, P. V. R.; Jiao, H.; Glukhovtsev, M. N.; Chandrasekhar, J.; Kraka, E. J. Am. Chem. Soc. 1994, 116, 10129.
25. [25]
  (25) Schleyer, P. V. R.; Maerker, C.; Dransfeld, A.; Jiao, H. J.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317.
26. [26]
  (26) Cissell, J. A.; Vaid, T. P.; Yap, G. P. A. Org. Lett. 2006, 8, 2401.
1. [1]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
2. [2]
  Huiying Xu , Minghui Liang , Zhi Zhou , Hui Gao , Wei Yi . Application of Quantum Chemistry Computation and Visual Analysis in Teaching of Weak Interactions. University Chemistry, 2025, 40(3): 199-205. doi: 10.12461/PKU.DXHX202407011
3. [3]
  Jinghan Xu , Yang Wang , Donghui Wei . Drawing Cross-Sectional Contour Maps of π Molecular Orbitals. University Chemistry, 2025, 40(3): 23-29. doi: 10.12461/PKU.DXHX202403023
4. [4]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
5. [5]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
6. [6]
  Linhan Tian , Changsheng Lu . Discussion on Sextuple Bonding in Diatomic Motifs of Chromium Family Elements. University Chemistry, 2024, 39(8): 395-402. doi: 10.3866/PKU.DXHX202401056
7. [7]
  Xuyang Wang , Jiapei Zhang , Lirui Zhao , Xiaowen Xu , Guizheng Zou , Bin Zhang . Theoretical Study on the Structure and Stability of Copper-Ammonia Coordination Ions. University Chemistry, 2024, 39(3): 384-389. doi: 10.3866/PKU.DXHX202309065
8. [8]
  Peng GENG , Guangcan XIANG , Wen ZHANG , Haichuang LAN , Shuzhang XIAO . Hollow copper sulfide loaded protoporphyrin for photothermal-sonodynamic therapy of cancer cells. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1903-1910. doi: 10.11862/CJIC.20240155
9. [9]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
10. [10]
  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
11. [11]
  Xiaosong PU , Hangkai WU , Taohong LI , Huijuan LI , Shouqing LIU , Yuanbo HUANG , Xuemei LI . Adsorption performance and removal mechanism of Cd(Ⅱ) in water by magnesium modified carbon foam. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1537-1548. doi: 10.11862/CJIC.20240030
12. [12]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
13. [13]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
14. [14]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
15. [15]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
16. [16]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
17. [17]
  Jiying Liu , Zehua Li , Wenjing Zhang , Donghui Wei . Molecular Orbital and Nucleus-Independent Chemical Shift Calculations for C₆H₆ and B₁₂H₁₂^2-: A Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 186-192. doi: 10.12461/PKU.DXHX202406085
18. [18]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
19. [19]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
20. [20]
  Xinlong WANG , Zhenguo CHENG , Guo WANG , Xiaokuen ZHANG , Yong XIANG , Xinquan WANG . Enhancement of the fragile interface of high voltage LiCoO₂ by surface gradient permeation of trace amounts of Mg/F. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 571-580. doi: 10.11862/CJIC.20230259

Get Citation

PDF

XML

Metrics

PDF Downloads(1259)
Abstract views(3025)
HTML views(7)

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