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- W2023381851 abstract "The ring inversion equilibrium in carbomethoxycyclohexane is compared with those in 2-carbomethoxy-tetrahydropyran and 2-carbomethoxypiperidine through a variable temperature nmr study of the positions of equilibria. The derived ΔHoa→e values (kcal mol−1) of −1.24 (cyclohexane), −1.69 (tetrahydropyran) and −0.54 (piperidine) can be rationalised in terms of competition between steric effects and endo-anomeric effects of the ring heteroatom. Variable temperature studies have also given ΔHoa→e values (kcal mol−1) for ring inversions in cyanocyclohexane, 2-cyanotetrahydropyran and 2-cyanopiperidine as −0.18, +0.36 and +2.22. Steric effects are small for CN, and the trend in ΔH° values is consistent with the expected increase in stabilising endo-anomeric effect along the series C, O, N." @default.
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- W2023381851 date "1992-01-01" @default.
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- W2023381851 title "Experimental studies of the anomeric effect. Part VI. Ring inversion equilibria in cyclohexane, tetrahydropyran and piperidine rings substituted by a carbomethoxy or a cyano group." @default.
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