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Communication | Special issue | Vol 33, No. 1, 1992, pp.35-38
Published online, 1st January, 1970
DOI: 10.3987/COM-91-S6
Spin-Spin Coupling between Fluorine and Aromatic Protons of 3-Fluoroquinoline: Dependence on the Electronic Structure of the Ring Nitrogen

Ken-ichi Saeki, Kohfuku Kohda, Yutaka Kawazoe,* and Yohko Sakamoto

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


The spin-spin coupling constant, J 2H- 3F , of 3-fluoroquinoline was strongly dependent on the electronic structure of the ring nitrogen. J 2H-3F measured in CDCl3 was almost null and increased as the acidity of solvent increased, reaching 2.8 Hz in 10% D2SO4. The J values of its methiodide and N-oxide were 3.1-3.3 and 3.8-4.6, respectively, which were not appreciably dependent on the acidity of the solvent for measurement.