Citation: Qiu-Yan ZHANG, Zhu-Yan HUANG, Yi LE, Xue ZOU, Zhi-Xu ZHOU, Chun-Shen ZHAO. Synthesis, Crystal Structure and DFT Study of 6-Hydroxybentazon[J]. Chinese Journal of Structural Chemistry, ;2020, 39(2): 269-278. doi: 10.14102/j.cnki.0254–5861.2011–2467 shu

Synthesis, Crystal Structure and DFT Study of 6-Hydroxybentazon

Qiu-Yan ZHANG ^{a, c} ,
Zhu-Yan HUANG ^{b, c} ,
Yi LE ^{b, c} ,
Xue ZOU ^d ,
Zhi-Xu ZHOU ^{b, c} ,
Chun-Shen ZHAO ^{b, c, e,,}

a.
School of Chemistry and Chemical Engineering, Guizhou University, Guiyang 550025, China
b.
School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025, China
c.
Guizhou Engineering Laboratory for Synthetic Drugs, Guiyang 550025, China
d.
Clinical Research Center, Affiliated Hospital of Guizhou Medical University, Guiyang 550001, China
e.
Key Laboratory of Guizhou for Fermentation Engineering and Biomedicine, Guiyang 550025, China

Corresponding author: Chun-Shen ZHAO, chunshenzhao@163.com
Received Date: 20 May 2019
Accepted Date: 6 September 2019

Fund Project: the Major Social Development Project SY20143054the Science and Technology Program of Guizhou Province [2017]1049the Science and Technology Cooperation Program of Guizhou Province LH20167442

Figures(4)

6-Hydroxybentazon, a metabolite of bentazon, was synthesized and characterized herein. The structure of the title compound 11 was verified by single-crystal X-ray crystallography. The optimized crystal structure as well as the HOMO and LUMO levels of the title compound was determined by density functional theory calculations at the B3LYP/6-311G(d, p) level.
- 6-hydroxybentazon,
- synthesis,
- crystal structure,
- DFT
1. [1]
  Boivin, A.; Cherrier, R.; Perrin-Ganier, C.; Schiavon, M. Time effect on bentazone sorption and degradation in soil. Pest. Manag. Sci. 2004, 60, 809–814. doi: 10.1002/ps.889
2. [2]
  Chiarandini, J. P.; Escandar, G. M. Nylon membrane as a fluorimetric probe for the herbicide bentazone. Anal. Bioanal. Chem. 2012, 402, 2221–2225. doi: 10.1007/s00216-011-5682-z
3. [3]
  Bruzzoniti, M. C.; De Carlo, R. M.; Rivoira, L.; Del Bubba, M.; Pavan, M.; Riatti, M.; Onida, B. Adsorption of bentazone herbicide onto mesoporous silica: application to environmental water purification. Environ. Sci. Pollut. Res. 2016, 23, 5399–5409. doi: 10.1007/s11356-015-5755-1
4. [4]
  Odjegba, V. J.; Adeniran, R. A. Bentazone herbicide induces genotoxic effect and physiological disorders in non-targeted Allium cepa L. Indian. J. Plant. Physiol. 2015, 20, 375–379. doi: 10.1007/s40502-015-0168-1
5. [5]
  Martinez, A.; Castro, A.; Gil, C.; Miralpeix, M.; Segarra, V.; Doménech, T.; Beleta, J.; Palacios, J. M.; Ryder, H.; Miró, X.; Bonet, C.; Casacuberta, J. M.; Azorín, F.; Puigdoménech, P. Benzyl derivatives of 2, 1, 3-benzo-and benzothieno [3, 2-a] thiadiazine 2, 2-dioxides: first phosphodiesterase 7 inhibitors. J. Med. Chem. 2000, 43, 683–689. doi: 10.1021/jm990382n
6. [6]
  Castro, A.; Abasolo, M. I.; Gil, C.; Segarra, V.; Martinez, A. CoMFA of benzyl derivatives of 2, 1, 3-benzo and benzothieno [3, 2-a] thiadiazine 2, 2-dioxides: clues for the design of phosphodiesterase 7 inhibitors. Eur. J. Med. Chem. 2001, 36, 333–338. doi: 10.1016/S0223-5234(01)01227-2
7. [7]
  Qi, X.; Fu, Z. T.; Li, L.; Hu, X. M.; Sun, H. B. A green synthesis technique of bentazone without discharging waste water Vols. 396-398. Tokyo: Advanced Materials Research, 2012, 2023–2026.
8. [8]
  Le, Y.; Zhao, C. S.; Zhou, Z. X.; Liu, L.; Huang, Z. Y.; Teng, M. G. Method for preparing 6-hydroxybentazone. CN patent, C07. 106478548. 2017-05-08.
9. [9]
  Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structures. University of Göttingen, Germany 1997.
10. [10]
  Mori, T.; Inoue, Y.; Grimme, S. Time dependent density functional theory calculations for electronic circular dichroism spectra and optical rotations of conformationally flexible chiral donor-acceptor dyad. J. Org. Chem. 2006, 71, 9797–9806. doi: 10.1021/jo061855i
11. [11]
  Marchesan, D.; Coriani, S.; Forzato, C.; Nitti, P.; Pitacco, G.; Ruud, K. Optical rotation calculation of a highly flexible molecule: the case of paraconic acid. J. Phys. Chem. A 2005, 109, 1449–1453. doi: 10.1021/jp047108b
12. [12]
  Kwit, M.; Sharma, N. D.; Boyd, D. R.; Gawronski, J. Determination of absolute configuration of conformationally flexible cis-dihydrodiol metabolites: effect of diene substitution pattern on the circular dichroism spectra and optical rotations. Chirality 2008, 20, 609–620. doi: 10.1002/chir.20471
13. [13]
  Deppmeier, B. J.; Driessen, A. J.; Hehre, T. S.; Hehre, W. J.; Johnson, J. A.; Klunzinger, P. E.; Kong, J. Wavefunction Inc, Spartan'08., Irvine, CA 2008.
14. [14]
  Bosnich, B. Molecular mechanics force fields for cyclopentadienyl complexes. Chem. Soc. Rev. 1994, 23, 387–395. doi: 10.1039/cs9942300387
15. [15]
  Huang, N.; Kalyanaraman, C.; Bernacki, K.; Jacobson, M. P. Molecular mechanics methods for predicting protein-ligand binding. Phys. Chem. Chem. Phys. 2006, 8, 5166–5177. doi: 10.1039/B608269F
16. [16]
  Koch, W.; Holthausen, M. C.; Holthausen, M. C. BUCHER-A chemist's guide to density functional theory. Angew. Chem. Ger. Edit. 2001, 113, 989–989.
17. [17]
  Geerlings, P.; De Proft, F.; Langenaeker, W. Conceptual density functional theory. Chem Rev. 2003, 103, 1793–1874. doi: 10.1021/cr990029p
18. [18]
  Saberikia, I.; Safaei, E.; Kowsari, M. H.; Lee, Y. I.; Cotic, P.; Bruno, G.; Rudbari, H. A. A new iron(Ⅲ) complex of glycine derivative of amine-chloro substituted phenol ligand: synthesis, characterization and catechol dioxygenase activity. J. Mol. Struct. 2012, 1029, 60–67. doi: 10.1016/j.molstruc.2012.06.047
1. [1]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
2. [2]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
3. [3]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
4. [4]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
5. [5]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
6. [6]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
7. [7]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
8. [8]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
9. [9]
  Tsegaye Tadesse Tsega , Jiantao Zai , Chin Wei Lai , Xin-Hao Li , Xuefeng Qian . Earth-abundant CuFeS2 nanocrystals@graphite felt electrode for high performance aqueous polysulfide/iodide redox flow batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100192-100192. doi: 10.1016/j.cjsc.2023.100192
10. [10]
  Chen Chen , Jinzhou Zheng , Chaoqin Chu , Qinkun Xiao , Chaozheng He , Xi Fu . An effective method for generating crystal structures based on the variational autoencoder and the diffusion model. Chinese Chemical Letters, 2025, 36(4): 109739-. doi: 10.1016/j.cclet.2024.109739
11. [11]
  Run-Han Li , Tian-Yi Dang , Wei Guan , Jiang Liu , Ya-Qian Lan , Zhong-Min Su . Evolution exploration and structure prediction of Keggin-type group IVB metal-oxo clusters. Chinese Chemical Letters, 2024, 35(5): 108805-. doi: 10.1016/j.cclet.2023.108805
12. [12]
  Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C₃N₄ for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767
13. [13]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
14. [14]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
15. [15]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
16. [16]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
17. [17]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
18. [18]
  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
19. [19]
  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
20. [20]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(313)
HTML views(16)

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