equatorial position. Though an equatorial substituent has no 1,3 diaxial interaction that causes steric strain, it has a Gauche interaction in which an equatorial substituent repels the electron density from a neighboring equatorial substituent. Disubstituted cyclohexanes For 1,2- and 1,4-disubstituted cyclohexanes, a cis configuration leads to one axial and one equatorial group. Such species undergo rapid, degenerate chair flipping. For 1,2- and 1,4-disubstituted cyclohexane, a trans configuration, the diaxial conformation is effectively prevented by its high steric strain. For 1,3-disubstituted cyclohexanes, the cis form is diequatorial and the flipped conformation suffers additional steric interaction between the two axial groups. trans-1,3-Disubstituted cyclohexanes are like cis-1,2- and cis-1,4- and can flip between the two equivalent axial/equatorial forms. Cis-1,4-Di-tert-butylcyclohexane has an axial tert-butyl group in the chair conformation and conversion to the twist-boat conformation places both groups in more favorable equatorial positions. As a result, the twist-boat conformation is more stable by at as measured by NMR spectroscopy. Also, for a disubstituted cyclohexane, as well as more highly substituted molecules, the aforementioned A values are additive for each substituent. For example, if calculating the A value of a dimethylcyclohexane, any methyl group in the axial position contributes 1.70 kcal/mol- this number is specific to methyl groups and is different for each possible substituent. Therefore, the overall A value for the molecule is 1.70 kcal/mol per methyl group in the axial position. 1,3 diaxial interactions and gauche interactions 1,3 Diaxial interactions occur when the non-hydrogen substituent on a cyclohexane occupies the axial position. This axial substituent is in the eclipsed position with the axial substituents on the 3-carbons relative to itself (there will be two such carbons and thus two 1,3 diaxial interactions). This eclipsed position increases the steric strain on the cyclohexane conformation and the confirmation will shift towards a more energetically favorable equilibrium. Gauche interactions occur when a non-hydrogen substituent on a cyclohexane occupies the equatorial position. The equatorial substituent is in a staggered position with the 2-carbons relative to itself (there will be two such carbons and thus two 1,2 gauche interactions). This creates a dihedral angle of ~60°. This staggered position is generally preferred to the eclipsed positioning. Effects of substituent size on stability Once again, the conformation and position of groups (ie. substituents) larger than a singular hydrogen are critical to the overall stability of the molecule. The larger the group, the less likely to prefer the axial position