The seeming lack of CF…HO intramolecular hydrogen bonds in linear aliphatic fluoroalcohols in solution
Abstract
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.
Citation
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
Publication
Physical Chemistry Chemical Physics
Status
Peer reviewed
ISSN
1463-9076Type
Journal article
Description
The 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).Collections
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