The seeming lack of CF…HO intramolecular hydrogen bonds in linear aliphatic fluoroalcohols in solution
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No CF…HO intramolecular hydrogen bonds (IHBs) in 2-fluoroethanol, 3-fluoropropanol and 4-fluorobutanol can be detected experimentally in solution by NMR and infrared spectroscopies. According to ab initio (MP2/aug-cc-pVDZ) and DFT calculations (B3LYP), a CF…HO IHB has no influence on the conformational behavior of 2-fluoroethanol, while it stabilises the global minima of 3-fluoropropanol and 4-fluorobutanol for the isolated molecules. Entropy and bulk solvation effects, even in nonpolar media, such as CCl4, cyclohexane and dichloromethane, are indicated to diminish the population of these global minima, apparently below the detection limit.
Cormanich , R A , Rittner , R , Freitas , M P & Buehl , M 2014 , ' The seeming lack of CF … HO intramolecular hydrogen bonds in linear aliphatic fluoroalcohols in solution ' , Physical Chemistry Chemical Physics , vol. 16 , no. 36 , pp. 19212-19217 . https://doi.org/10.1039/c4cp02463j
Physical Chemistry Chemical Physics
© Royal Society of Chemistry 2014. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://dx.doi.org/10.1039/C4CP02463J
DescriptionThe authors acknowledge a Grant #2012/03933-5, São Paulo Research Foundation (FAPESP) for providing financial support for this research (scholarship to RAC #2011/01170-1, FAPESP). FAPEMIG (Minas Gerais Research Foundation) is also acknowledged, such as CNPq for fellowships (to RR and MPF) and a studentship (to RAC).
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