Citation: CUI Ying-Na, YIN Jing-Mei, JIA Ying-Ping, LI Shen-Min. Experimental and Density Functional Theoretical Studies on the Spectra of N,N'-di[3-hydroxy-4-(2-benzothiazole)phenyl]urea[J]. Acta Physico-Chimica Sinica, ;2015, 31(9): 1647-1654. doi: 10.3866/PKU.WHXB201506182 shu

Experimental and Density Functional Theoretical Studies on the Spectra of N,N'-di[3-hydroxy-4-(2-benzothiazole)phenyl]urea

1.
1 College of Environment and Chemical Engineering, Dalian University, Dalian 116622, Liaoning Province, P. R. China;
2 Liaoning Key Laboratory of Bio-organic Chemistry, Dalian University, Dalian 116622, Liaoning Province, P. R. China

Received Date: 11 May 2015
Available Online: 18 June 2015
Fund Project: 国家自然科学基金(21133005) (21133005) 辽宁省自然科学基金(201205535) (201205535)辽宁省教育厅2010年度高等学校科研项目(重点实验室项目)(LS2010005)资助 (重点实验室项目)(LS2010005)

The experimental infrared (IR), nuclear magnetic resonance (NMR), and ultraviolet (UV) spectra, and density functional theory (DFT) calculations of the novel compound N,N'-di[3-hydroxy-4-(2-benzothiazole) phenyl]urea (4-DHBTU) are presented. Compared with the UV spectra of the 2-(4-amino-2-hydroxyphenyl) benzothiazole (4-AHBT) monomer, the experimental spectra of 4-DHBTU, a dimer of 4-AHBT, show dualwavelength absorption with significantly enhanced absorption intensity and an obvious red shift of the maximum absorption peak. Analysis of the experimental spectra and the DFT calculations shows that the structures of cis-C₁₁ and trans-C₁₁ are the two most stable conformers, and that the main reason for the different UV spectral properties of the dimer and monomer is the coexistence of cis-C₁₁, trans-C₁₁, cis-C₂₂, and trans-C₂₂ in the 4-DHBTU sample. In addition, the DFT calculations indicate that a hydrogen-bonding interaction between 4-DHBTU and the dimethyl sulfoxide (DMSO) solvent leads to a large 1H NMR chemical shift for atoms 15H and 16H in 4-DHBTU.
- N,N'-di[3-hydroxy-4-(2-benzothiazole)phenyl]urea,
- Ultraviolet spectroscopy,
- Excited state,
- Density functional theory
1. [1]
  
  (1) Ma, D.; Liang, F. S.; Wang, L. X.; Lee, S. T.; Hung, L. S. Chem. Phys. Lett. 2002, 358, 24. doi: 10.1016/S0009-2614(02)00546-8
2. [2]
  (2) Rodembusch, F. S.; Tia , B.; Segala, M.; Tavares, L.; Correia, R. R. B.; Stefani, V. Chem. Phys. 2004, 305, 115. doi: 10.1016/j.chemphys.2004.06.046
3. [3]
  (3) Tolbert, L. M.; Solntsev, K. M. Accounts Chem. Res. 2002, 35, 19. doi: 10.1021/ar990109f
4. [4]
  (4) Ma, Q. J.; Zhang, X. B.; Zhao, X. H.; ng, Y. J.; Tang, J.; Shen, G. L.; Yu, R. Q. Spectrochim. Acta Part A 2009, 73, 687. doi: 10.1016/j.saa.2009.03.023
5. [5]
  (5) Henary, M. M.; Fahrni, J. C. J. Phys. Chem. A 2002, 106, 5210. doi: 10.1021/jp014634j
6. [6]
  (6) Zhang, X. B.; Peng, J.; He, C. L.; Shen, G. L.; Yu, R. Q. Anal. Chim. Acta 2006, 567, 189. doi: 10.1016/j.aca. 2006.03.025
7. [7]
  (7) Qin, W.; Obare, S. O.; Murphy, C. J.; Angel, S. M. Anal. Chem. 2002, 74, 4757. doi: 10.1021/ac020365x
8. [8]
  (8) Purkayastha, P.; Chattopadhyay, N. Int. J. Mol. Sci. 2003, 4, 335. doi: 10.3390/i4060335
9. [9]
  (9) Chipem, F. A. S.; Krishnamoorthy, G. J. Phys. Chem. B 2013, 117, 14079. doi: 10.1021/jp405804c
10. [10]
  (10) Luber, S.; Adamczyk, K.; Nibbering, E. T. J.; Batista, V. S. J. Phys. Chem. A 2013, 117, 5269. doi: 10.1021/jp403342w
11. [11]
  (11) Benelhadj, K.; Massue, J.; Retailleau, P.; Ulrich, G.; Ziessel R. Org. Lett. 2013, 15, 2918.
12. [12]
  (12) Padalkar, V. S.; Tathe, A. B.; Gupta, V. D.; Patil, V. S.; Phatangare, K.; Sekar, N. J. Fluoresc. 2012, 22, 311. doi: 10.1007/s10895-011-0962-8
13. [13]
  (13) Patil, V. S.; Padalkar, V. S.; Tathe, A. B.; Gupta, V. D.; Sekar, N. J. Fluoresc. 2013, 23, 1019.
14. [14]
  (14) Zhao, J. Z.; Ji, S. M.; Chen, Y. H.; Guo, H. M.; Yang, P. Phys. Chem. Chem. Phys. 2012, 14, 8803. doi: 10.1039/c2cp23144a
15. [15]
  (15) Abou-Zied, O. K. Phys. Chem. Chem. Phys. 2012, 14, 2832. doi: 10.1039/c2cp23337a
16. [16]
  (16) Abou-Zied, O. K. RSC Adv. 2013, 3, 8747. doi: 10.1039/c3ra40907d
17. [17]
  (17) Syetov, Y. J. Fluoresc. 2013, 23, 689. doi: 10.1007/s10895-013-1196-8
18. [18]
  (18) Rodembusch, F. S.; Leusin, F. P.; Campo, L. F.; Stefani, V. J. Lumin. 2007, 126, 728. doi: 10.1016/j.jlumin. 2006.11.007
19. [19]
  (19) Wu, Y. F.; Cui, Y. N.; Li, S. M.; Jia, Y. P.; Yin, J. M. Chin. J. Inorg. Chem. 2012, 28, 910. [吴玉防, 崔颖娜, 李慎敏, 贾颖萍, 尹静梅. 无机化学学报, 2012, 28, 910.]
20. [20]
  (20) Yin, J. M.; Yang, Q.; Jia, Y. P.; Cui, Y, N.; Zhou, G. Y.; Gao, D. B. Synthesis and Application of N, N'-di[3-hydroxy-4-(2-benzothiazole)phenyl]urea. CN Patent ZL200910012518.6, 2011-05-25. [尹静梅, 阳强, 贾颖萍, 崔颖娜, 周广运, 高大彬. 一种N, N'-二-[3-羟基-4-(2-苯并噻唑)苯基]脲的合成方法及应用, 中国, ZL200910012518.6[P], 2011-05-25.]
21. [21]
  (21) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218. doi: 10.1063/1.477483
22. [22]
  (22) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454. doi: 10.1016/0009-2614(96)00440-X
23. [23]
  (23) Peng, H. L.; Yu, X. Y.; Yi, P. G.; Wang, Z. X.; Li, X. F.; Wang, T.; Zhou, J. M. Acta Phys. -Chim. Sin. 2010, 26, 141. [彭洪亮, 于贤勇, 易平贵, 汪朝旭, 李筱芳, 王涛, 周继明. 物理化学学报, 2010, 26, 141.] doi: 10.3866/PKU.WHXB 20100130
24. [24]
  (24) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03, Revision B.04; Gaussian Inc.: Pittsburgh, PA, 2003.
25. [25]
  (25) Yuan, Y. J.; He, R. X.; Hu, G. J.; Li, M. Journal of Southwest University (Natural Science Edition) 2009, 31, 55. [袁彦杰, 何荣幸, 胡广剑, 李明. 西南大学学报(自然科学版), 2009, 31, 55.]
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