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
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