Why is gauche conformer of 2,3-dimethylbutane seen along 2,3 bond more stable than its anti conformer? It seems to be anomalous to me as in most other butane like compunds anti form is more stable than gauche form.Can someone explain me the reason why the compound shows Gauche effect?

Also does this anomaly hold in case of 2,3-diphenylbutane and 2,3-dimethylpentane?

  • $\begingroup$ Related: Conformations of butane and How can the gauche-effect be explained? $\endgroup$
    – user7951
    Aug 4, 2016 at 9:24
  • $\begingroup$ @Loong I saw those links.They do not explain the case of 2,3-dimethylbutane. $\endgroup$
    – user14857
    Aug 4, 2016 at 9:41
  • $\begingroup$ I am also confused by this and asked a more general question here. When it's answered, if it doesn't also answer yours, I'll be happy to come back here. $\endgroup$
    – SCH
    Aug 4, 2016 at 16:53
  • $\begingroup$ @S.Chevalier Your question is different from mine.Your one is answered in Wikipedia page I linked named Gauche Effect in my question above. $\endgroup$
    – user14857
    Aug 4, 2016 at 16:58
  • $\begingroup$ Could it be possible that the conformation where the hydrogens are anti is called gauche? $\endgroup$ Aug 5, 2016 at 10:21


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