| Full text | |
| Author(s): |
Port, Vinicius C.
;
Zeoly, Lucas A.
;
Coelho, Fernando
;
Cormanich, Rodrigo A.
Total Authors: 4
|
| Document type: | Journal article |
| Source: | Physical Chemistry Chemical Physics; v. 23, n. 15, p. 9-pg., 2021-04-21. |
| Abstract | |
Given its importance and the possibility of organic F to participate in hydrogen bonds (H-bonds), the understanding of its behavior as a H-bond acceptor with different donors is crucial. The interest in organofluorine compounds and the works related to the study of the participation of this atom in non-covalent interactions is constantly growing. Following recent studies in this subject, we evaluated the existence of two bifurcated intramolecular interactions, a bifurcated CF center dot center dot center dot HS H-bond in the cis conformer of 2-trifluoromethylthiophenol and an unusual, bifurcated CF center dot center dot center dot SH interaction in the trans conformer. The JFH spin-spin coupling constant (SSCC) was evaluated for 2-trifluoromethylthiophenol both experimentally by H-1 and F-19 NMR and theoretically using the natural bond orbitals (NBO), the quantum theory of atoms in molecules (QTAIM) and the non-covalent interactions (NCI) framework. Although both interactions are crucial for the stabilization of the conformer geometries, the observed positive JFH spin-spin coupling constant (SSCC) is mainly resultant from the trans conformer, which has a large calculated positive SSCC, and is transmitted through steric interactions involving the F lone pairs and the sSH bonding orbital. (AU) | |
| FAPESP's process: | 18/03910-1 - Physicochemical studies of fluorinated organic compounds: experimental and theoretical approaches |
| Grantee: | Rodrigo Antonio Cormanich |
| Support Opportunities: | Research Grants - Young Investigators Grants |