Synthesis, crystal structure, Hirshfeld surface analysis and DFT calculations of 2, 2, 2-tribromo-1-(3,5-dibromo-2-hydroxyphenyl)ethanone
JOURNAL OF MOLECULAR STRUCTURE, vol.1248, 2022 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 1248
- Publication Date: 2022
- Doi Number: 10.1016/j.molstruc.2021.131313
- Journal Name: JOURNAL OF MOLECULAR STRUCTURE
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
- Keywords: Brominated compound, Coumarin derivatives, X-ray diffraction, DFT calculation, Hirshfeld analysis, MAXIMUM HARDNESS, SPECTRUM, GAS, NBO
- Sivas Cumhuriyet University Affiliated: Yes
Abstract
A novel derivative 2, 2, 2-tribromo-1-(3,5-dibromo-2-hydroxyphenyl) ethanone was synthesis by "3-acetyl-4-hydroxycoumarin" and dibromide. The structural properties of the synthesized compound have been exploited with the aid of single-crystal X-ray crystallographic studies and infrared spectrometry. The compound crystallizes in the monoclinic system with space group P2(1)/c. A comparative study between the novel brominated compound synthesized and the brominated coumarin derivative is presented. The optimized DFT geometries (B3PW91/6-311 G (2df, p)) and the spectral simulations of two derivatives compared agree well with the experimental data. Hirshfeld's analysis revealed the importance of Br center dot center dot center dot Br (40%) and Br center dot center dot center dot H/H center dot center dot center dot Br (19%) of the total surface contacts in the molecular stack. The contacts O center dot center dot center dot H/H center dot center dot center dot O have a significant contribution for the brominated coumarin (C2) of 26.1% of SH compared to the brominated cycle (C1) 9.7%. (C) 2021 Published by Elsevier B.V.