372-93-0Relevant articles and documents
Structure, conformations, and internal hydrogen bonding in gaseous 4-fluorobutan-1-ol. Gas-phase electron diffraction and Ab initio study
Traetteberg, Marit,Richardson, Alan D.,Hedberg, Kenneth,Winter, Rolf W.,Gard, Gary L.
, p. 9587 - 9594 (2001)
Excluding enantiomers, there are 14 possible rotomeric conformations of 4-fluorobutan-1-ol, of which two are capable of forming an internal O-H...F hydrogen bond. The composition of the gaseous system is of special interest because it is determined by the energies of the conformers which reflect the energies of the hydrogen bonds. We have investigated the conformational composition of the gaseous system and the molecular structures of the conformers at 83 °C by gas-phase electron diffraction (GED) augmented by molecular orbital calculations. Because of the complexity of the 4-fluorobutan-1-ol system, the parameters of the several models tested were simplified by various constraints taken from the theoretical work. With these constraints, the best agreement with the GED data was obtained with a model consisting of about equal amounts of hydrogen-bonded and non-hydrogen-bonded conformers. Because the curled-up shape of the two forms capable, in principle, of forming internal hydrogen bonds is expected to be energetically unfavorable in the absence of such bonding, the experimental results are interpreted as strong evidence for its existence. Weighted average values, with estimated 2σ uncertainties, of the more important bond distances (ra/A) and bond angles (∠a/deg) for the preferred model are r(Co-C) = 1.529(2), r(CC-CC) = 1.537(2), r(C-CF) = 1.520(2), r(C-O) = 1.430(5), r(C-F) = 1.401(5), ∠(Co-C-C) = 112.5(33), ∠(C-C-O)H bond = 112.3(55), ∠(C-C-O)no H bond = 108.2(45), and ∠(C-C-CF) = 109.8(12). The two hydrogen-bonded conformers comprise 48.5% of the mixture with an estimated 2σ uncertainty of 14.0%. A rough estimate of the energy of the O-H...F hydrogen bond is 3 kcal mol-1. The average O...F separation in this bond for the H-bonded conformers is 2.46(4) A, about 0.3 A less than the sum of the van der Waals radii.
A novel fluorinated erythromycin antibiotic
Goss, Rebecca J. M.,Hong, Hui
, p. 3983 - 3985 (2007/10/03)
A novel fluorinated erythromycin (16-fluoroerythromycin A) has been produced by Saccharopolyspora erythraea ERMD1, using precursor-directed biosynthesis. The Royal Society of Chemistry 2005.
REACTION OF HYDROXY AND CARBONYL COMPOUNDS WITH SULFUR TETRAFLUORIDE IX. REACTIONS OF GLYCOLS WITH SULFUR TETRAFLUORIDE
Hassanein, Salah Mohamed,Burmakov, A. I.,Bloshchitsa, F. A.,Yagupol'skii, L. M.
, p. 1473 - 1477 (2007/10/02)
Selective substitution of one of the hydroxyl groups by a fluorine atom occurs in the reactions of 1,2-, 1,3-, and 1,4-glycols with sulfur tetrafluoride under mild conditions.The regioselectivity of substitution in the case of unsymmetrical glycols depends on the electronic nature of the groups present in the molecules of the initial compounds.
