Citation: Liang MA, Qing-Zhao YAO, Yu-Ming ZHOU, Ming-Liang WANG, Bai-Wang SUN, Yi XUE, Chang GUO. Synthesis, Crystal Structures, Hirshfeld Surfaces, Thermo Characteristics and Solubility of Co-crystal of Buprofezin with Hydrofluoric Acid[J]. Chinese Journal of Structural Chemistry, ;2020, 39(3): 500-510. doi: 10.14102/j.cnki.0254–5861.2011–2569 shu

Synthesis, Crystal Structures, Hirshfeld Surfaces, Thermo Characteristics and Solubility of Co-crystal of Buprofezin with Hydrofluoric Acid

Liang MA ^a ,
Qing-Zhao YAO ^a ,
Yu-Ming ZHOU ^{a, c,,} ,
Ming-Liang WANG ^a ,
Bai-Wang SUN ^a ,
Yi XUE ^{a, b, c} ,
Chang GUO ^{a, c}

a.
School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China
b.
Nanjing Red Sun Biochemical Co., Ltd., Nanjing 210000, China
c.
Southeast University Red Sun Research Center for Intelligent Industry, Nanjing 211189, China

Corresponding author: Yu-Ming ZHOU, fchem@163.com
Received Date: 12 August 2019
Accepted Date: 15 November 2019

Fund Project: the National Natural Science Foundation of China 51673040the Natural Science Foundation of Jiangsu Province BK20180366the Natural Science Foundation of Jiangsu Province BK20171357the Fundamental Research Funds for the Central Universities 2242019k30042Scientific Innovation Research Foundation of College Graduate in Jiangsu Province KYLX16_0266a Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PADA) 1107047002Fund Project for Transformation of Scientific and Technological Achievements of Jiangsu Province of China BA2018045

Figures(12)

A new kind of co-crystal of buprofezin (C₁₆H₂₄FN₃OS) with hydrofluoric acid has been prepared through evaporation technique. It crystallizes in the triclinic space group P\begin{document}$ \overline 1 $\end{document}, with a = 9.9733(8), b = 10.3460(9), c = 10.5739(12) Å, α = 68.655(9), β = 73.291(9), γ = 66.738(8)º, V = 920.34(17) Å³, M_r = 325.44, D_c = 1.174 g/cm³, Z = 2, F(000) = 348, μ = 0.190 mm^-1, the final GOOF = 1.042, R = 0.0485 and wR = 0.1167. Single-crystal X-ray diffraction, XRPD, DSC, TGA, Hirshfeld surface analysis, Raman spectroscopy and FT-IR were used to characterize the co-crystal. It has a two-dimensional plane structure, and the intermolecular interactions of co-crystal are mainly H–F⋅⋅⋅H, H–O⋅⋅⋅H and H–O⋅⋅⋅H. Thermology study further confirmed that co-crystal has stronger thermal stability and higher melting point than buprofezin, and it has stronger water solubility. The results show that this co-crystal is valuable for the study of residual activity and application effects of buprofezin.
- co-crystal,
- buprofezin,
- X-ray,
- thermal stability
1. [1]
  Dunitz, J. D.; Gavezzotti, A. How molecules stick together in organic crystals: weak intermolecular interactions. Chem. Soc. Rev. 2009, 38, 2622-2633. doi: 10.1039/b822963p
2. [2]
  Xiao, M.; Xian, Y.; Shi, F. Precise macroscopic supramolecular assembly by combining spontaneous locomotion driven by the Marangoni effect and molecular recognition. Angew. Chem. Int. Edit. 2015, 54, 8952-8956. doi: 10.1002/anie.201502349
3. [3]
  Seth, S. K.; Das, N. K.; Aich, K.; Sen, D.; Fun, H. K.; Goswami, S. Exploring contribution of intermolecular interactions in supramolecular layered assembly of naphthyridine co-crystals: insights from Hirshfeld surface analysis of their crystalline states. J. Mol. Struct. 2013, 1048, 157-165. doi: 10.1016/j.molstruc.2013.05.048
4. [4]
  Schneider, H. J. Binding mechanisms in supramolecular complexes. Angew. Chem. Int. Edit. 2009, 48, 3924-3977. doi: 10.1002/anie.200802947
5. [5]
  Ling, A. R. LII. Studies on isomeric change. No. Ⅳ. Halogen derivatives of quinone. Part Ⅰ. J. Chem. Soc., Trans. 1892, 61, 558-581. doi: 10.1039/CT8926100558
6. [6]
  Parthasarathi, R.; Subramanian, V.; Sathyamurthy, N. Hydrogen bonding without borders: an atoms-in-molecules perspective. J. Phys. Chem. A 2006, 110, 3349-3351. doi: 10.1021/jp060571z
7. [7]
  Shimizu, G. K. H.; Vaidhyanathan, R.; Taylor, J. M. Phosphonate and sulfonate metal organic frameworks. Chem. Soc. Rev. 2009, 38, 1430-1449. doi: 10.1039/b802423p
8. [8]
  Liu, X. G.; Bao, S. S.; Li, Y. Z.; Zheng, L. M. Polymorphism in homochiral zinc phosphonates. Inorg. Chem. 2008, 47, 5525-5527. doi: 10.1021/ic800663t
9. [9]
  Nechipadappu, S. K.; Trivedi, D. R. Cocrystal of nutraceutical sinapic acid with active pharmaceutical ingredients ethenzamide and 2-chloro-4-nitrobenzoic acid: equilibrium solubility and stability study. J. Mol. Struct. 2018, 1171, 898-905. doi: 10.1016/j.molstruc.2018.06.074
10. [10]
  Zhou, P.; Liang, Y.; Zhang, H.; Jiang, H.; Feng, K.; Xu, P.; Wang, J.; Wang, X.; Ding, K.; Luo, C.; Liu, M.; Wang, Y. Design, synthesis, biological evaluation and cocrystal structures with tubulin of chiral β-lactam bridged combretastatin A-4 analogues as potent antitumor agents. Eur. J. Med. Chem. 2018, 144, 817-842. doi: 10.1016/j.ejmech.2017.12.004
11. [11]
  Qin, X.; Hao, Z.; Tian, Q.; Zhang, Z.; Zhou, C.; Xie, W. Cocrystal structures of glycyl-tRNA synthetase in complex with tRNA suggest multiple conformational states in glycylation. J. Biol. Chem. 2014, 289, 20359-20369. doi: 10.1074/jbc.M114.557249
12. [12]
  Ames, B.; Nguyen, C.; Bruegger, J.; Smith, P.; Xu, W.; Ma, S.; Wong, E.; Wong, S.; Xie, X.; Li, W. H.; Vederas, J.; Tang, Y.; Tsai, S. C. Crystal structure and biochemical studies of the trans-acting polyketide enoyl reductase LovC from lovastatin biosynthesis. Proc. Natl. Acad. Sci. 2012, 109, 11144-11149. doi: 10.1073/pnas.1113029109
13. [13]
  Shaikh, R.; Singh, R.; Walker, G. M.; Croker, D. M. Pharmaceutical cocrystal drug products: an outlook on product development. Trends Pharmacol. Sci. 2018, 39, 1033-1048. doi: 10.1016/j.tips.2018.10.006
14. [14]
  Yan, Y.; Chen, J.; Lu, T. B. Simultaneously enhancing the solubility and permeability of acyclovir by crystal engineering approach. CrystEngComm. 2013, 15, 6457-6460. doi: 10.1039/c3ce41017j
15. [15]
  Khan, E.; Shukla, A.; Jadav, N.; Telford, R.; Ayala, A. P.; Tandon, P.; Vangala, V. R. Study of molecular structure, chemical reactivity and H-bonding interactions in the cocrystal of nitrofurantoin with urea. New J. Chem. 2017, 41, 11069-11078. doi: 10.1039/C7NJ01345K
16. [16]
  Pandey, J.; Prajapati, P.; Shimpi, M.; Tandon, P.; Velaga, S.; Srivastava, D. A.; Sinha, K. Studies of molecular structure, hydrogen bonding and chemical activity of a nitrofurantoin-L-proline cocrystal: a combined spectroscopic and quantum chemical approach. RSC Adv. 2016, 6, 74135-74154. doi: 10.1039/C6RA13035F
17. [17]
  Srivastava, K.; Khan, E.; Shimpi, M.; Tandon, P.; Sinha, K.; Velaga, S. Molecular structure and hydrogen bond interactions of a paracetamol-4, 4'-bipyridine cocrystal studied using vibrational spectroscopic and quantum chemical approach. CrystEngComm. 2017, 20, 213-222.
18. [18]
  Cabras, P.; Angioni, A.; Garau, V.; Melis, M.; Pirisi, F.; Cabitza, F.; Dedola, F.; Navickiene, S. Determination of buprofezin, pyridaben, and tebufenpyrad residues by gas chromatography-mass-selective detection in clementine citrus. J. Agric. Food Chem. 1998, 46, 4255-4259. doi: 10.1021/jf9802171
19. [19]
  Wang, Z.; Zhou, C.; Long, G. Y.; Yang, H.; Jin, D. C. Sublethal effects of buprofezin on development, reproduction, and chitin synthase 1 gene (SfCHS1) expression in the white-backed planthopper, Sogatella furcifera (Hemiptera: Delphacidae). J. Asia-Pac. Entomol. 2018, 21, 585-591. doi: 10.1016/j.aspen.2018.03.009
20. [20]
  Ali, E.; Liao, X.; Yang, P.; Mao, K.; Zhang, X.; Shakeel, M.; Markaz, A.; Wan, H.; Li, J. Sublethal effects of buprofezin on development and reproduction in the white-backed planthopper, Sogatella furcifera (Hemiptera: Delphacidae). Sci. Rep. 2017, 05, 16913-9.
21. [21]
  Zia Qureshi, I.; Bibi, A.; Shahid, S.; Ghazanfar, M. Exposure to sub-acute doses of fipronil and buprofezin in combination or alone induces biochemical, hematological, histopathological and genotoxic damage in common carp (Cyprinus carpio L. ). Aquat. Toxicol. 2016, 179, 103-114. doi: 10.1016/j.aquatox.2016.08.012
22. [22]
  Ji, X.; Ku, T.; Zhu, N.; Ning, X.; Wei, W.; Li, G.; Sang, N. Potential hepatic toxicity of buprofezin at sublethal concentrations: ros-mediated conversion of energy metabolism. J. Hazard. Mater. 2016, 320, 176-186. doi: 10.1016/j.jhazmat.2016.08.027
23. [23]
  Wang, G.; Xu, D.; Xiong, M.; Zhang, H.; Li, F.; Liu, Y. Novel degradation pathway and kinetic analysis for buprofezin removal by newly isolated Bacillus sp. J. Environ. Manage. 2016, 180, 59-67. doi: 10.1016/j.jenvman.2016.04.061
24. [24]
  Zhu, Z.; Zhou, Y.; Yao, Q.; Sun, B.; Wang, M.; Zhong, X.; Wang, B.; Xue, Y.; Chen, X. Two polymorphs and a sulfate of buprofezin: crystal structure and Hirshfeld surface analysis. Polyhedron 2018, 155, 85-93. doi: 10.1016/j.poly.2018.08.034
25. [25]
  Chen, X.; Zhou, Z.; Chen, J.; Chu, C.; Zheng, J.; Wang, S.; Jia, W.; Zhao, J.; Li, R.; Han, D. Solubility determination and thermodynamic modeling of buprofezin in different solvents and mixing properties of solutions. J. Chem. Eng. Data 2019, 64, 1177-1186. doi: 10.1021/acs.jced.8b01099
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