November 13, 2024, 02:02:17 AM
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Topic: substituent increased stability on the equatorial position true for only chairs?  (Read 2688 times)

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Offline iScience

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is this just for the case of cyclohexane chairs or are all substituents on any cycloalkane ring more stable on the equatorial position?

Offline discodermolide

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What do you mean by stable?
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Offline iScience

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lower in energy.

we're learning about aromatic conformations and where the substituents should go on them. and one of the things i remember hearing was that the substituents want to be on the equatorial position; and i heard this over and over when we were working with chair conformations of hexane, but i was wondering if this was true for all the other ring conformations like boat, cyclopentane, cycloheptane, cycloocane, etc etc

Offline discodermolide

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Yes, the equatorial position is usually lower energy than the axial.
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Offline TwistedConf

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we're learning about aromatic conformations and where the substituents should go on them. and one of the things i remember hearing was that the substituents want to be on the equatorial position; and i heard this over and over when we were working with chair conformations of hexane, but i was wondering if this was true for all the other ring conformations like boat, cyclopentane, cycloheptane, cycloocane, etc etc

Not "aromatic"...  cyclic.

Cyclohexane chairs are uniquely un-strained in their special "chair" conformations... with specific "axial" and "equatorial" positions. All cyclic alkanes do preferentially adopt conformations that minimize steric and torsional strain...  but those conformations are not typically called "chair" conformations with axial/equatorial positions like a ring of 6.

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