Computational evidence for intramolecular hydrogen bonding and nonbonding X···O interactions in 2'-haloflavonols

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• Chiari, C.; Batista, P. R.; Viesser, R. V.; Schenberg, L. A.; Ducati, L. C.; Linclau, B.; Tormena, C. F. Molecular dynamics and NMR reveal the coexistence of H-bond-assisted and through-space JFH coupling in fluorinated amino alcohols. Organic & biomolecular chemistry 2024, 22, 2580–2595. doi:10.1039/d4ob00049h
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• Mzozoyana, V.; van Heerden, F. R.; Grimmer, C. D. 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 2020, 16, 190–199. doi:10.3762/bjoc.16.22
• Burai-Patrascu, M.-R.
• O'Reilly, D.; Stein, R. S.; Patrascu, M. B.; Jana, S. K.; Kurian, J.; Moitessier, N.; Damha, M. J. Exploring Atypical Fluorine–Hydrogen Bonds and Their Effects on Nucleoside Conformations. Chemistry (Weinheim an der Bergstrasse, Germany) 2018, 24, 16432–16439. doi:10.1002/chem.201803940
• Silla, J. M.; Silva, D. R.; Freitas, M. P. Theoretical Study on the Conformational Bioeffect of the Fluorination of Acetylcholine. Molecular informatics 2017, 36, 1700084. doi:10.1002/minf.201700084
• Carreño, A.; Gacitúa, M.; Molins, E.; Arratia-Pérez, R. X-ray diffraction and relativistic DFT studies on the molecular biomarker fac-Re(CO)3(4,4′-dimethyl-2,2′-bpy)(E-2-((3-amino-pyridin-4-ylimino)-methyl)-4,6-di-tert-butylphenol)(PF6). Chemical Papers 2017, 71, 2011–2022. doi:10.1007/s11696-017-0196-6
• Mandal, A.; Patel, B. K.; Shukla, R.; Chopra, D. Impact of the complementary electronic nature of C–X and M–X halogens and intramolecular X⋯O interaction on supramolecular assemblies of Zn(II) complexes of o-halophenyl substituted hydrazides. CrystEngComm 2017, 19, 1607–1619. doi:10.1039/c7ce00060j
• Silla, J. M.; Freitas, M. P. A halogen bond does not dictate the conformational preferences of cis-1,3-disubstituted cyclohexanes. Organic & biomolecular chemistry 2016, 14, 8610–8614. doi:10.1039/c6ob01635a
• Pichierri, F. Molecular triskelions: structure and bonding in the perhalogenated analogues of boric acid, X3BO3 (X=F, Cl, Br, I). Structural Chemistry 2016, 28, 213–223. doi:10.1007/s11224-016-0835-5
• Sun, H.; Li, H. Theoretical studies on the proton-transfer reactions in propylene and pentadiene derivatives. Structural Chemistry 2014, 26, 587–597. doi:10.1007/s11224-014-0521-4
• Cormanich, R. A.; Rittner, R.; Freitas, M. P.; Bühl, M. The seeming lack of CF⋯HO intramolecular hydrogen bonds in linear aliphatic fluoroalcohols in solution. Physical chemistry chemical physics : PCCP 2014, 16, 19212–19217. doi:10.1039/c4cp02463j
• Yasarawan, N.; Thipyapong, K.; Ruangpornvisuti, V. Exploring molecular structures, orbital interactions, intramolecular proton-transfer reaction kinetics, electronic transitions and complexation of 3-hydroxycoumarin species using DFT methods. Journal of molecular graphics & modelling 2014, 51, 13–26. doi:10.1016/j.jmgm.2014.04.009
• Cormanich, R. A.; Santiago, R. T.; La Porta, F. A.; Freitas, M. P.; Rittner, R.; da Cunha, E. F. F.; Andrés, J.; Longo, E.; Ramalho, T. C. Quantum chemical topological analysis of hydrogen bonding in HX…HX and CH3X…HX dimers (X = Br, Cl, F). Molecular Simulation 2014, 41, 600–609. doi:10.1080/08927022.2014.904514
• Silla, J. M.; Cormanich, R. A.; Rittner, R.; Freitas, M. P. Conformational analysis and intramolecular interactions in monosubstituted phenylboranes and phenylboronic acids. Beilstein journal of organic chemistry 2013, 9, 1127–1134. doi:10.3762/bjoc.9.125
• Champagne, P. A.; Pomarole, J.; Thérien, M. È.; Benhassine, Y.; Beaulieu, S.; Legault, C. Y.; Paquin, J.-F. Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding. Organic letters 2013, 15, 2210–2213. doi:10.1021/ol400765a
• Silla, J. M.; Cormanich, R. A.; Rittner, R.; Freitas, M. P. Conformational analysis and intramolecular interactions in aminofluorobenzoic acids. The journal of physical chemistry. A 2013, 117, 1659–1664. doi:10.1021/jp311791g
• Silla, J. M.; Duarte, C. J.; Rittner, R.; Freitas, M. P. Conformational analysis of 6-fluorosalicylic acid. RSC Advances 2013, 3, 25765–25768. doi:10.1039/c3ra43241f

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