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
Full text not available from this repository. (Request a copy)Abstract
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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