Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds
4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (JFH = 2.6 Hz) and 13C NMR suggested that this C–F···H–C coupling is a thr...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2020-02-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.16.22 |
| id |
doaj-2a2694ac20ce4ab8943570382789bac1 |
|---|---|
| record_format |
Article |
| spelling |
doaj-2a2694ac20ce4ab8943570382789bac12021-03-02T07:53:03ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-02-0116119019910.3762/bjoc.16.221860-5397-16-22Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bondsVuyisa Mzozoyana0Fanie R. van Heerden1Craig Grimmer2School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville, 3209, Pietermaritzburg, South AfricaSchool of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville, 3209, Pietermaritzburg, South AfricaSchool of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville, 3209, Pietermaritzburg, South Africa4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (JFH = 2.6 Hz) and 13C NMR suggested that this C–F···H–C coupling is a through-space interaction. The 2D 19F-{1H} HOESY and 1H-{19F} 1D experiments were done to confirm this F···H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C–F···H–C interaction.https://doi.org/10.3762/bjoc.16.22dftf···h hydrogen bondfluorinated phenylcoumarinpechmann reactionthrough-space coupling |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Vuyisa Mzozoyana Fanie R. van Heerden Craig Grimmer |
| spellingShingle |
Vuyisa Mzozoyana Fanie R. van Heerden Craig Grimmer Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds Beilstein Journal of Organic Chemistry dft f···h hydrogen bond fluorinated phenylcoumarin pechmann reaction through-space coupling |
| author_facet |
Vuyisa Mzozoyana Fanie R. van Heerden Craig Grimmer |
| author_sort |
Vuyisa Mzozoyana |
| title |
Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds |
| title_short |
Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds |
| title_full |
Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds |
| title_fullStr |
Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds |
| title_full_unstemmed |
Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds |
| title_sort |
synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular c–f···h–c bonds |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2020-02-01 |
| description |
4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (JFH = 2.6 Hz) and 13C NMR suggested that this C–F···H–C coupling is a through-space interaction. The 2D 19F-{1H} HOESY and 1H-{19F} 1D experiments were done to confirm this F···H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C–F···H–C interaction. |
| topic |
dft f···h hydrogen bond fluorinated phenylcoumarin pechmann reaction through-space coupling |
| url |
https://doi.org/10.3762/bjoc.16.22 |
| work_keys_str_mv |
AT vuyisamzozoyana synthesisof42fluorophenyl7methoxycoumarinexperimentalandcomputationalevidenceforintramolecularandintermolecularcfhcbonds AT faniervanheerden synthesisof42fluorophenyl7methoxycoumarinexperimentalandcomputationalevidenceforintramolecularandintermolecularcfhcbonds AT craiggrimmer synthesisof42fluorophenyl7methoxycoumarinexperimentalandcomputationalevidenceforintramolecularandintermolecularcfhcbonds |
| _version_ |
1724240932175347712 |