March 29, 2024, 10:16:19 AM
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Topic: Benzyl group larger than phenyl group, but has a smaller diaxial interaction?  (Read 1994 times)

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Offline mee-ow

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Why would a benzyl group have a smaller diaxial interaction than a phenyl group (in a monosubstituted cyclohexane)?

Offline AWK

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Think about labile conformation of benzyl group.
AWK

Offline mee-ow

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Would you mind expanding a bit please?

EDIT: So, I'm thinking that, with the benzyl-substituted cyclohexane, the CH2 is closer to the axial hydrogens, so it participates more in the 1,3-diaxial interactions than the larger C6H5. With the phenyl-substituted cyclohexane the C6H5 is what interacts with the axial hydrogens.
« Last Edit: October 02, 2016, 02:43:34 PM by mee-ow »

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