Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex
The most stable isomer of the 1:1 complex formed by 2,2,2-trifluoroacetophenone and water has been characterized by combining rotational spectroscopy in supersonic expansion and state-of-the-art quantum-chemical computations. In the observed isomer, water plays the double role of proton donor and ac...
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MDPI AG
2020-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/21/4899 |
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| author | Juncheng Lei Silvia Alessandrini Junhua Chen Yang Zheng Lorenzo Spada Qian Gou Cristina Puzzarini Vincenzo Barone |
| author_facet | Juncheng Lei Silvia Alessandrini Junhua Chen Yang Zheng Lorenzo Spada Qian Gou Cristina Puzzarini Vincenzo Barone |
| author_sort | Juncheng Lei |
| collection | DOAJ |
| description | The most stable isomer of the 1:1 complex formed by 2,2,2-trifluoroacetophenone and water has been characterized by combining rotational spectroscopy in supersonic expansion and state-of-the-art quantum-chemical computations. In the observed isomer, water plays the double role of proton donor and acceptor, thus forming a seven-membered ring with 2,2,2-trifluoroacetophenone. Accurate intermolecular parameters featuring one classical O-H···O hydrogen bond and one weak C-H···O hydrogen bond have been determined by means of a semi-experimental approach for equilibrium structure. Furthermore, insights on the nature of the established non-covalent interactions have been unveiled by means of different bond analyses. The comparison with the analogous complex formed by acetophenone with water points out the remarkable role played by fluorine atoms in tuning non-covalent interactions. |
| first_indexed | 2024-03-10T15:23:46Z |
| format | Article |
| id | doaj.art-82a69b98d6bb452897d996b2f7c3c06d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T15:23:46Z |
| publishDate | 2020-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-82a69b98d6bb452897d996b2f7c3c06d2023-11-20T18:13:58ZengMDPI AGMolecules1420-30492020-10-012521489910.3390/molecules25214899Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water ComplexJuncheng Lei0Silvia Alessandrini1Junhua Chen2Yang Zheng3Lorenzo Spada4Qian Gou5Cristina Puzzarini6Vincenzo Barone7Department of Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Daxuecheng South Rd. 55, Chongqing 401331, ChinaScuola Normale Superiore, Piazza dei Cavalieri 7, I-56126 Pisa, ItalyDepartment of Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Daxuecheng South Rd. 55, Chongqing 401331, ChinaDepartment of Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Daxuecheng South Rd. 55, Chongqing 401331, ChinaScuola Normale Superiore, Piazza dei Cavalieri 7, I-56126 Pisa, ItalyDepartment of Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Daxuecheng South Rd. 55, Chongqing 401331, ChinaDepartment of Chemistry “Giacomo Ciamician”, University of Bologna, Via Selmi 2, 40126 Bologna, ItalyScuola Normale Superiore, Piazza dei Cavalieri 7, I-56126 Pisa, ItalyThe most stable isomer of the 1:1 complex formed by 2,2,2-trifluoroacetophenone and water has been characterized by combining rotational spectroscopy in supersonic expansion and state-of-the-art quantum-chemical computations. In the observed isomer, water plays the double role of proton donor and acceptor, thus forming a seven-membered ring with 2,2,2-trifluoroacetophenone. Accurate intermolecular parameters featuring one classical O-H···O hydrogen bond and one weak C-H···O hydrogen bond have been determined by means of a semi-experimental approach for equilibrium structure. Furthermore, insights on the nature of the established non-covalent interactions have been unveiled by means of different bond analyses. The comparison with the analogous complex formed by acetophenone with water points out the remarkable role played by fluorine atoms in tuning non-covalent interactions.https://www.mdpi.com/1420-3049/25/21/4899hydrogen bondquantum chemistryrotational spectroscopynoncovalent interactionssubstituent effectsstructure |
| spellingShingle | Juncheng Lei Silvia Alessandrini Junhua Chen Yang Zheng Lorenzo Spada Qian Gou Cristina Puzzarini Vincenzo Barone Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex Molecules hydrogen bond quantum chemistry rotational spectroscopy noncovalent interactions substituent effects structure |
| title | Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex |
| title_full | Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex |
| title_fullStr | Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex |
| title_full_unstemmed | Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex |
| title_short | Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex |
| title_sort | rotational spectroscopy meets quantum chemistry for analyzing substituent effects on non covalent interactions the case of the trifluoroacetophenone water complex |
| topic | hydrogen bond quantum chemistry rotational spectroscopy noncovalent interactions substituent effects structure |
| url | https://www.mdpi.com/1420-3049/25/21/4899 |
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