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Topic: Benzyl group larger than phenyl group, but has a smaller diaxial interaction?  (Read 2256 times)

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Offline mee-ow

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Benzyl group larger than phenyl group, but has a smaller diaxial interaction?
« on: October 02, 2016, 01:28:43 PM »
Why would a benzyl group have a smaller diaxial interaction than a phenyl group (in a monosubstituted cyclohexane)?
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Offline AWK

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Re: Benzyl group larger than phenyl group, but has a smaller diaxial interaction?
« Reply #1 on: October 02, 2016, 01:33:55 PM »
Think about labile conformation of benzyl group.
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Offline mee-ow

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Re: Benzyl group larger than phenyl group, but has a smaller diaxial interaction?
« Reply #2 on: October 02, 2016, 01:41:27 PM »
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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