Journal of the American Chemical Society p. 3007 - 3010 (1989)
Update date:2022-09-26
Topics:
Pascal, Robert A.
Winans, Charles G.
Van Engen, Donna
The syntheses of 2,8,17-trithia-in-<35,12><9>metacyclophane, 2,7,16-trithia-in-<35,11><8>metacyclophane, and 2,6,15-trithia-in-<34,10><7>metacyclophane are described.Due to the extreme proximity of the apical methine hydrogen atoms and the centers of the aromatic rings, the compounds display very high field 1H NMR resonances and very high frequency IR C-H stretching bands.X-ray crystallographic analyses of the latter two compounds reveal hydrogen-to-ring distances of only 1.81 and 1.69 Angstroem, respectively.The experimentally determined geometries are contrasted with structures generated by molecular mechanics and semiempirical molecular orbital calculations.
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(1989)
