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An NMR study of the conformational equilibrium of 5‐fluoro‐1,3‐dioxan in solution. Dependence on solvent
Author(s) -
Hall L. D.,
Johnson R. N.
Publication year - 1972
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270040303
Subject(s) - substituent , cyclohexane , chemistry , solvent , chloroform , fluorine , polar , cyclohexane conformation , fluorine 19 nmr , computational chemistry , crystallography , stereochemistry , nuclear magnetic resonance spectroscopy , organic chemistry , molecule , hydrogen bond , physics , astronomy
The 1 H and 19 F NMR parameters of 5‐fluoro‐1,3‐dioxan ( 1 ) dissolved in a number of solvent systems are interpreted on the basis of fast inversion between two chair conformations. In cyclohexane solution the two chair conformations are almost equally populated, whereas in more polar solvents, such as chloroform, the conformation having the fluorine substituent in an axial position is strongly preferred. Addition of acetic acid to a solution of 1 in cyclohexane increases the preference of the fluorine substituent for the axial orientation. Possible reasons for these observations are discussed.