4-Chloro-3-fluorobenzaldehyde: Experimental (XRD, FT-IR and Raman) and DFT studies

Parlak, C. and Chidan Kumar, C. S. and Fun, H. K. and Kesan, G. and Rhyman, L. and Ramasami, P. and Chandraju, S. and Quah, C. K. (2014) 4-Chloro-3-fluorobenzaldehyde: Experimental (XRD, FT-IR and Raman) and DFT studies. Journal of Fluorine Chemistry, 163. pp. 7-15. ISSN 0022-1139

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Official URL: https://doi.org/10.1016/j.jfluchem.2014.03.014


The structure of 4-chloro-3-fluorobenzaldehyde (CFB, C7H 4ClFO) has been characterized by single-crystal X-ray diffraction, FT-IR and Raman techniques. The conformational isomers, optimized geometrical parameters, normal mode frequencies and corresponding vibrational assignments of CFB have been examined using the density functional theory method, with the Becke-3-Lee-Yang-Parr functional and the 6-311+G(3df,p) basis set. Reliable vibrational assignments and molecular orbitals have been investigated by the potential energy distribution. CFB crystallizes in monoclinic space group P21/c with the O-cis conformation. In order to examine the effect of fluorine on the conformational preference, the chloro- and bromo-analogs of CFB have also been studied theoretically. It is observed that CFB prefers the O-cis conformation while the chloro- and bromo-analogs prefer the O-trans conformation. Although the free energy difference between the O-cis and O-trans conformers is less than 0.2 kcal/mol, the free energy rotational barrier is at least 8.4 kcal/mol B3LYP/6-311+G(3df,p). MP2/aug-cc-pVDZ computations reveal that these free energies remain almost unaffected. The atypical characteristic of fluorine affecting conformational isomerism is observed. In addition, there is a good agreement between the experimentally determined structural parameters and vibrational frequencies of CFB and those predicted theoretically.

Item Type: Article
Subjects: D Physical Science > Sugar Technology
Divisions: PG Centre Mandya > Sugar Technology
Depositing User: Arshiya Kousar Library Assistant
Date Deposited: 03 Jul 2019 05:47
Last Modified: 10 Jul 2019 05:50
URI: http://eprints.uni-mysore.ac.in/id/eprint/4524

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