Citation: Hui-Liang WEN, Bo-Wen LAI, Hua-Long PENG, Zhi-Qiang XIONG, Chong-Bo LIU. Characterization and Infrared Stealthy Properties of Two Schiff-base Compounds Derived from 1-Amino-2-hydroxypropane and Their Complexes[J]. Chinese Journal of Structural Chemistry, ;2020, 39(2): 279-286. doi: 10.14102/j.cnki.0254–5861.2011–2420 shu

Characterization and Infrared Stealthy Properties of Two Schiff-base Compounds Derived from 1-Amino-2-hydroxypropane and Their Complexes

a.
State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China
b.
Chemicals Analysis Department, Nanchang Institute for Food and Drug Control, Nanchang 330038, China
c.
School of Environment and Chemical Engineering, Nanchang Hangkong University, Nanchang 330063, China

Corresponding author: Chong-Bo LIU, cbliu2002@163.com
Received Date: 19 April 2019
Accepted Date: 19 September 2019

Fund Project: the National Natural Science Foundation of China 21264011the National Natural Science Foundation of China 20961007the State Key Laboratory of Food Science and Technology of Nanchang University SKLF-ZZB-201519

Figures(5)

Single crystals of two Schiff base compounds 1 and 2 derived from 1-amino-2-hydroxypropane were obtained via condensation reaction of an amine and a reactive carbonyl group. The compounds were characterized by elemental analysis, IR and single-crystal X-ray diffraction. Compound 1 (C₁₀H₁₃NO₂) crystallizes in the monoclinic system, space group P2₁ with a = 4.487(9), b = 10.913(2), c = 9.886(19) Å, β = 97.823(3)º, V = 479.59(16) Å³, Z = 2, M_r = 179.21, D_c = 1.241 g/cm³, F(000) = 192, GOOF = 1.005, μ = 0.087 mm^-1, the final R = 0.0328 and wR = 0.0738 for 1721 observed reflections with I > 2σ(I). Compound 2 (C₁₄H₂₀N₂O₂) crystallizes in orthorhombic system, space group Pbca with a = 6.295(2), b = 7.290(3), c = 30.519(11) Å, V = 1400.5(9) Å³, Z = 8, M_r = 248.32, D_c = 1.178 g/cm³, F(000) = 536, GOOF = 1.125, μ = 0.079 mm^-1, the final R = 0.0871 and wR = 0.1748 for 1307 observed reflections with I > 2σ(I). Compound 1 exhibits a 3D supramolecular structure and compound 2 show a 3D supramolecular structure under hydrogen bonding interactions. Furthermore, the infrared stealthy performance of two Schiff base compounds and their Fe(Ⅲ) complexes were studied. The results show that their Fe(Ⅲ) complexes show lower infrared emissivity than corresponding Schiff base compounds, and the lowest infrared emissivity reaches to 0.657.
- two Schiff base compounds,
- 1-amino-2-hydroxypropane,
- crystal structure,
- Fe(Ⅲ) complexes,
- infrared stealth
1. [1]
  Macdonald, J. C.; Whitesides, G. M. Solid-state structures of hydrogen-bonded tapes based on cyclic secondary diamides. Chem. Rev. 1994, 94, 2383–2420. doi: 10.1021/cr00032a007
2. [2]
  Wang, L.; Xu, L. Y.; Xue, R. F.; Lu, X. F.; Chen, R. X.; Tao, X. T. Cocrystallization of N-donor type compounds with 5-sulfosalicylic acid: the effect of hydrogen-bonding supramolecular architectures. Science China Chemistry 2012, 55, 138–144. doi: 10.1007/s11426-011-4394-8
3. [3]
  Shen, C. J.; Sheng, T. L.; Fu, R. B.; Hu, S. M.; Chen, J. S.; Zhu, Q. L.; Ma, X.; Wu, X. T. Dinuclear copper(Ⅱ) complex with a new polycarboxylate ligand: syntheses, characterization and crystal structure. Chin. J. Struct. Chem. 2012, 31, 11–18.
4. [4]
  Benito, J. M.; Gomez-Garcia, M.; Mellet, C. O.; Baussanne, I.; Defaye, J.; Fernandez, J. M. Optimizing saccharide-directed molecular delivery to biological receptors: design, synthesis, and biological evaluation of glycodendrimer-cyclodextrin conjugates. J. Am. Chem. Soc. 2004, 126, 10355–10363. doi: 10.1021/ja047864v
5. [5]
  Shaheen, F.; Rehman, Z. U.; Ali, S.; Meetsma, A. Structural properties and antibacterial potency of new supramolecular organotin(Ⅳ) dithiocarboxylates. Polyhedron 2012, 31, 697–703. doi: 10.1016/j.poly.2011.10.025
6. [6]
  Ishow, E.; Bellaiche, C.; Bouteiller, L.; Nakatani, K.; Delaire, J. A. Versatile synthesis of small NLO-active molecules forming amorphous materials with spontaneous second-order NLO response. J. Am. Chem. Soc. 2003, 125, 15744–15745. doi: 10.1021/ja038207q
7. [7]
  Miyahira, T.; Hasegawa, H.; Takahashi, Y.; Inabe, T. Electrochemical crystallization of organic molecular conductors: electrode surface conditions for crystal growth. Cryst. Growth Des. 2013, 13, 1955–1960. doi: 10.1021/cg301852k
8. [8]
  Marchal, C.; Filinchuk, Y.; Imbert, D.; Bunzli, J. C. G.; Mazzanti, M. Toward the rational design of lanthanide coordination polymers: a new topological approach. Inorg. Chem. 2007, 46, 6242–6244. doi: 10.1021/ic7009918
9. [9]
  Liu, C. B.; Chen, Y.; Yan, L. S.; Huang, D. H.; Xiong, Z. Q. Syntheses, characterization, and antibacterial activities of four new Schiff base compounds derived from 1-phenyl-3-methyl-4-benzoyl-2-pyrazolin-5-one. J. Heterocycl. Chem. 2012, 49, 839–844. doi: 10.1002/jhet.874
10. [10]
  Hadjoudis, E.; Vittorakis, M.; Moustakali-Mavridis, I. Photochromism and thermochromism of Schiff bases in the solid state and in rigid glasses. J. Tetrahedron 1987, 43, 1345–1360. doi: 10.1016/S0040-4020(01)90255-8
11. [11]
  Akitsu, T.; Einaga, Y. Synthesis, crystal structures and electronic properties of Schiff base nickel(Ⅱ) complexes: towards solvatochromism induced by a photochromic solute. Polyhedron 2005, 24, 1869–1877. doi: 10.1016/j.poly.2005.06.019
12. [12]
  Li, H. N.; Liu, C. B.; Dai, B.; Tang, X. H.; Zhang, Z. J.; Xiong, Z. Q.; Liu, X. M. Synthesis, conductivity and electromagnetic wave absorption properties of chiral poly Schiff bases and their silver complexes. J. Appl. Polym. Sci. 2015, 132, 10815(1-8).
13. [13]
  Liu, C. B.; Li, L.; Zhang, X.; Chen, W. Y.; Zhang, Z. J.; Qin, Y. C.; Chen, D. Z. Synthesis, characterization of chiral poly(ferrocenyl-Schiff base) iron(Ⅱ) complexes/RGO composites with enhanced microwave absorption properties. Polymer. 2018, 150, 301–310. doi: 10.1016/j.polymer.2018.07.049
14. [14]
  Kundua, B. K.; Chhabraa, V.; Malviyaa, N.; Gangulyb, R.; Mishrac, G. S.; Mukhopadhyay, S. Zeolite encapsulated host-guest Cu(Ⅱ) Schiff base complexes: superior activity towards oxidation reactions over homogenous catalytic systems. Micropor. Mesopor. Mater. 2018, 271, 100–117. doi: 10.1016/j.micromeso.2018.05.046
15. [15]
  Gupta, K. C.; Sutara, A. K.; Lin, C. C. Polymer-supported Schiff base complexes in oxidation reactions. Coord. Chem. Rev. 2009, 253, 1926–1946. doi: 10.1016/j.ccr.2009.03.019
16. [16]
  Gupta, K. C.; Sutar, A. K. Catalytic activities of Schiff base transition metal complexes. J. Coord. Chem. Rev. 2008, 252, 1420–1450. doi: 10.1016/j.ccr.2007.09.005
17. [17]
  Kaczmarek, M. T.; Zabiszak, M.; Nowak, M.; Jastrzab, R. Lanthanides: Schiff base complexes, applications in cancer diagnosis, therapy, and antibacterial activity. Coord. Chem. Rev. 2018, 370, 42–54. doi: 10.1016/j.ccr.2018.05.012
18. [18]
  Wen, H. L.; Du, X. L.; Liu, C. B. Research advance of flavonoids carboxylic acid compounds and their rare earth complexes. Chin. Rare Earths 2009, 30, 69–75.
19. [19]
  Dhahagani, K.; Kesavan, M. P.; Kumar, G. G. V.; Ravi, L.; Rajagopal, G.; Rajesh, J. Crystal structure, optical properties, DFT analysis of new morpholine based Schiff base ligands and their copper(Ⅱ) complexes: DNA, protein docking analyses, antibacterial study and anticancer evaluation. Mater. Sci. Eng. C 2018, 90, 119–130. doi: 10.1016/j.msec.2018.04.032
20. [20]
  Gryboś, R.; Szklarzewicz, J.; Jurowska, A.; Hodorowicz, M. Properties, structure and stability of V(Ⅳ) hydrazide Schiff base ligand complex. J. Mol. Struct. 2018, 1171, 880–887. doi: 10.1016/j.molstruc.2018.06.077
21. [21]
  Kaczmarek, M. T.; Kubicki, M.; Hnatejko, Z. Two types of lanthanide Schiff base complexes: synthesis, structure and spectroscopic studies. Polyhedron 2015, 102, 224–232. doi: 10.1016/j.poly.2015.09.063
22. [22]
  Kaczmarek, M. T.; Jastrząb, R.; Kubicki, M.; Gierszewski, M.; Sikorski, M. Suplamolecular polymer of Schiff base gadolinium complex: synthesis, crystal structure and spectroscopic properties. Inorg. Chim. Acta 2015, 430, 108–113. doi: 10.1016/j.ica.2015.02.026
23. [23]
  Storr, T.; Thompson, K. H.; Orvig, C. Design of targeting ligands in medicinal inorganic chemistry. Chem. Soc. Rev. 2006, 35, 534–544. doi: 10.1039/b514859f
24. [24]
  Kumar, K.; Tweedle, M. F. Macrocyclic polyaminocarboxylate complexes of lanthanides as magnetic resonance imaging contrast agents. Pure Appl. Chem. 1993, 65, 515–520. doi: 10.1351/pac199365030515
25. [25]
  Gao, F.; Zhang, Y. Q.; Wang, S.; Liu, H.; Chen, X. Y. Syntheses, structures and magnetic properties of macrocyclic Schiff base-supported homodinuclear lanthanide complexes. Dalton Trans. 2018, 47, 11696–11704. doi: 10.1039/C8DT02243G
26. [26]
  Tessa ten Cate, A.; Kooijman, H.; Spek, A. L.; Sijbesma, R. P.; Meijer, E. W. Conformational control in the cyclization of hydrogen-bonded supramolecular polymers. J. Am. Chem. Soc. 2004, 126, 3801–3808. doi: 10.1021/ja039408x
27. [27]
  Tzeli, D.; Petsalakis, I. D.; Theodorakopoulos, G.; Ajami, D.; Rebek, J. J. Theoretical study of free and encapsulated carboxylic acid and amide dimers. Int. J. Quantum Chem. 2013, 113, 734–739. doi: 10.1002/qua.24062
28. [28]
  Wen, H. L.; Chen, Y. H.; Liu, C. B.; Chen, D. D.; Hu, X. B. Crystal structure of 3-Hydroxy-3΄, 4΄-methylenedioxy flavone-6-carboxylic acid dimethylformamide solvate. J. Chem. Crystallogr. 2010, 40, 731–734. doi: 10.1007/s10870-010-9727-5
29. [29]
  Shattock, T. R.; Vishweshwar, P.; Wang, Z. Q.; Zaworotko, M. J. 18-Fold interpenetration and concomitant polymorphism in the 2: 3 co-crystal of trimesic acid and 1, 2-bis(4-pyridyl)ethane. Cryst. Growth Des. 2005, 5, 2046–2049. doi: 10.1021/cg0501985
30. [30]
  Rajput, L.; Biradha, K. Design of cocrystals via new and robust supramolecular synthon between carboxylic acid and secondary amide: honeycomb network with jailed aromatics. Cryst. Growth Des. 2009, 9, 40–42. doi: 10.1021/cg801132r
31. [31]
  Varughese, S.; Pedireddi, V. R. A competitive molecular recognition study: syntheses and analysis of supramolecular assemblies of 3, 5-dihydroxybenzoic acid and its bromo derivative with some N-donor compounds. Chem. Eur. J. 2006, 12, 1597–1609. doi: 10.1002/chem.200500570
32. [32]
  Zhao, Y.; Li, Z.; Li, H.; Wang, S.; Niu, M. Synthesis, crystal structure, DNA binding and in vitro cytotoxicity studies of Zn(Ⅱ) complexes derived from amino-alcohol Schiff-bases. Inorg. Chim Acta 2018, 482, 136–143. doi: 10.1016/j.ica.2018.06.008
33. [33]
  Shankar, M.; Dennis, R. A.; Jeeva, M.; Purusothaman, R.; Vimalan, M.; Vetha, P. I. Synthesis, crystal growth, thermal and laser damage threshold properties of new Schiff base NLO material 4-nitro-benzoic acid (3-ethoxy-2-hydroxy-benzylidene)-hydrazide. Mate. Lett. 2018, 232, 113–117. doi: 10.1016/j.matlet.2018.08.090
34. [34]
  Hu, Y. X. The synthesis of different structure Schiff bases and their complexes for infrared emissivity property. Nanjing University of Aeronautics and Astronautics 2016.
35. [35]
  Fu, W. Electro-optic stealthy technology of aircraft. Electronics Optics & Control 2002, 01, 7–10.
36. [36]
  Hu, Y. X.; Zhuang, H. Y.; Xu, G. Y.; Yan, L. J. The synthesis and infrared stealth performance of Schiff-bases of different structures and their iron compounds. Develop Appl. Materi. 2016, 31, 55–60.
37. [37]
  Lv, X. L.; Xu, W. D.; Cui, C. A.; Chen, Y. H.; Ge, Q, L. The Synthesis of Schiff bases and their application in the low emissivity coating. J. PLA Univ. of Sci. Technol. 2000, 54–57.
38. [38]
  Sheldrick, G. M. SADABS. Program for Empirical Absorption Correction of the Area Detector Data. University of Gottingen, Germany 1997.
39. [39]
  Sheldrick, G. M. SHELXS-97. Program for Crystal Structure Solution. University of Gottingen, Germany 1997.
40. [40]
  Sheldrick, G. M. SHELXL-97. Program for Crystal Structure Refinement. University of Gottingen, Germany 1997.
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