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Article

Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex

1
Department of Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Daxuecheng South Rd. 55, Chongqing 401331, China
2
Scuola Normale Superiore, Piazza dei Cavalieri 7, I-56126 Pisa, Italy
3
Department of Chemistry “Giacomo Ciamician”, University of Bologna, Via Selmi 2, 40126 Bologna, Italy
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editors: Wiktor Zierkiewicz and Steve Scheiner
Molecules 2020, 25(21), 4899; https://doi.org/10.3390/molecules25214899
Received: 30 September 2020 / Revised: 20 October 2020 / Accepted: 21 October 2020 / Published: 23 October 2020
(This article belongs to the Special Issue Spectroscopic Aspects of Noncovalent Interactions)
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. View Full-Text
Keywords: hydrogen bond; quantum chemistry; rotational spectroscopy; noncovalent interactions; substituent effects; structure hydrogen bond; quantum chemistry; rotational spectroscopy; noncovalent interactions; substituent effects; structure
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MDPI and ACS Style

Lei, J.; Alessandrini, S.; Chen, J.; Zheng, Y.; Spada, L.; Gou, Q.; Puzzarini, C.; Barone, V. Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex. Molecules 2020, 25, 4899. https://doi.org/10.3390/molecules25214899

AMA Style

Lei J, Alessandrini S, Chen J, Zheng Y, Spada L, Gou Q, Puzzarini C, Barone V. Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex. Molecules. 2020; 25(21):4899. https://doi.org/10.3390/molecules25214899

Chicago/Turabian Style

Lei, Juncheng, Silvia Alessandrini, Junhua Chen, Yang Zheng, Lorenzo Spada, Qian Gou, Cristina Puzzarini, and Vincenzo Barone. 2020. "Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex" Molecules 25, no. 21: 4899. https://doi.org/10.3390/molecules25214899

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