Acta Phys. -Chim. Sin. ›› 2015, Vol. 31 ›› Issue (9): 1647-1654.doi: 10.3866/PKU.WHXB201506182


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

Ying-Na. CUI1,*(),Jing-Mei. YIN1,2,Ying-Ping. JIA1,Shen-Min. LI1,2,*()   

  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:2015-05-11 Published:2015-09-06
  • Contact: Ying-Na. CUI,Shen-Min. LI;
  • Supported by:
    the National Natural Science Foundation of China(21133005);National Natural Science Foundation of LiaoningProvince, China(201205535);Scientific Research Foundation of the Higher Education Institutions of Education Bureau of Liaoning Province(Key Laboratory Project 2010), China(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.

Key words: N, N'-di[3-hydroxy-4-(2-benzothiazole)phenyl]urea, Ultraviolet spectroscopy, Excited state, Density functional theory


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