Citation: Zhu Da, Hua Haiming, Huang Feng, Qiu Shun, Chen Jichao, Shi Jiuzhou, Xu Li, Lu Wen. Crystal Structure and Density Functional Theory Study of 3-Acetyl-8-tert-butyl-coumarin[J]. Chemistry, ;2019, 82(3): 258-263. shu

Crystal Structure and Density Functional Theory Study of 3-Acetyl-8-tert-butyl-coumarin

Zhu Da ¹ ,
Hua Haiming ² ,
Huang Feng ¹ ,
Qiu Shun ¹ ,
Chen Jichao ¹ ,
Shi Jiuzhou ¹ ,
Xu Li ¹ ,
Lu Wen ^1,,

1.
College of Science, Nanjing Forestry University, Nanjing 210037
2.
College of Chemistry and Chemistry Engineering, Xiamen University, Xiamen 361005

Corresponding author: Lu Wen, luwen@njfu.edu.cn
Received Date: 18 September 2018
Accepted Date: 2 November 2018

Figures(7)

3-Acetyl-8-tert-butylcoumarin was synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy and UV-Vis spectroscopy. Density functional theory was used to investigate the intermolecular weak interaction in crystal, simulate spectrum and predict active site which is possible to be attacked by electrophilic or nucleophile reagent. The results showed that the molecule is almost a planar structure which exists conjugation effect. Molecules in crystal are combined by π-π stacking between layers and hydrogen bonds in chains, and the binding energy of two molecules is 17.2 and 3.9 kcal/mol respectively. The wavelength of maximum absorption in the scope of near ultraviolet and visible light is about 310nm, and molar absorption coefficient is 16000 L·mol^-1·cm^-1, which was caused by π-electron of benzene ring transferring to inner ester ring and the oxygen atom of aldehyde group. No. 6 carbon is the most likely site to be attacked by electrophilic reagent in benzene ring. Inner ester is able to undergo hydrolysis or aminolysis reaction. The hydrogen atoms in the benzene ring and the oxygen atoms of carbonyl groups can both form weak interaction such as hydrogen bond.
- Coumarin,
- Crystal structure,
- DFT,
- Reactivity,
- Weak interaction
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沈阳化工大学材料科学与工程学院沈阳 110142