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Anomeric Effect

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Abstract

In substituted cyclohexanes, such as cyclohexanol or its methyl ether, the substituent will preferably assume the equatorial position as opposed to the axial one, due to fewer nonbonded interactions with other ligands (in this case the C3 and the C5 hydrogen atoms) on the cyclohexane ring [1–5]. Thus, the conformational mixture of cyclohexanol or its methyl ether contains, at equilibrium, 89% of the conformer with equatorially oriented hydroxyl or methoxy group and 11% of the conformer with axially oriented hydroxyl or methoxy group, indicating clear preference for the equatorial conformer (Fig. 3.1).

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    Momčilo Miljković

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Miljković, M. (2010). Anomeric Effect. In: Carbohydrates. Springer, New York, NY. https://doi.org/10.1007/978-0-387-92265-2_3

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