Through space J FH spin–spin coupling constant transmission pathways in 2-(trifluoromethyl)thiophenol: formation of unusual stabilizing bifurcated CF⋯HS and CF⋯SH interactions
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...
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| Published in | Physical chemistry chemical physics : PCCP Vol. 23; no. 15; pp. 9080 - 9088 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
22.04.2021
|
| Online Access | Get full text |
| ISSN | 1463-9076 1463-9084 |
| DOI | 10.1039/D0CP05887D |
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| 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⋯HS H-bond in the
cis
conformer of 2-trifluoromethylthiophenol and an unusual, bifurcated CF⋯SH interaction in the
trans
conformer. The
J
FH
spin–spin coupling constant (SSCC) was evaluated for 2-trifluoromethylthiophenol both experimentally by
1
H and
19
F 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
J
FH
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 σ
SH
bonding orbital. |
|---|---|
| AbstractList | 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⋯HS H-bond in the
cis
conformer of 2-trifluoromethylthiophenol and an unusual, bifurcated CF⋯SH interaction in the
trans
conformer. The
J
FH
spin–spin coupling constant (SSCC) was evaluated for 2-trifluoromethylthiophenol both experimentally by
1
H and
19
F 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
J
FH
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 σ
SH
bonding orbital. |
| Author | Port, Vinícius C. Coelho, Fernando Cormanich, Rodrigo A. Zeoly, Lucas A. |
| Author_xml | – sequence: 1 givenname: Vinícius C. orcidid: 0000-0003-2044-914X surname: Port fullname: Port, Vinícius C. organization: University of Campinas, Chemistry Institute, Campinas, Brazil – sequence: 2 givenname: Lucas A. surname: Zeoly fullname: Zeoly, Lucas A. organization: University of Campinas, Chemistry Institute, Campinas, Brazil – sequence: 3 givenname: Fernando orcidid: 0000-0003-1800-1549 surname: Coelho fullname: Coelho, Fernando organization: University of Campinas, Chemistry Institute, Campinas, Brazil – sequence: 4 givenname: Rodrigo A. orcidid: 0000-0001-7659-1749 surname: Cormanich fullname: Cormanich, Rodrigo A. organization: University of Campinas, Chemistry Institute, Campinas, Brazil |
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| CitedBy_id | crossref_primary_10_1039_D4OB00049H crossref_primary_10_1016_j_jfluchem_2023_110191 crossref_primary_10_1016_j_jfluchem_2025_110397 crossref_primary_10_1021_acs_jctc_4c01043 crossref_primary_10_1039_D4CE00983E crossref_primary_10_1039_D3CC05389J crossref_primary_10_1002_slct_202200666 |
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| Title | Through space J FH spin–spin coupling constant transmission pathways in 2-(trifluoromethyl)thiophenol: formation of unusual stabilizing bifurcated CF⋯HS and CF⋯SH interactions |
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