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Tert-butyl cyclohexane in two conformations

Dear Reader

OK I have some data for you, the best way I have found so far is to copy the data into a text file. Save it as an xyz file. Then you can open it with ORTEP to look at it from different angles.

This is cyclohexane with an axial tert-butyl group

 

30
XYZ file : axial tert butyl cyclohexane
C(1) -5.3864 -3.5864 -0.2151
C(2) -6.9117 -3.5562 -0.1674
C(3) -7.4874 -2.5768 -1.1867
C(4) -6.9739 -2.8638 -2.5951
C(5) -5.4486 -2.8938 -2.6428
C(6) -4.8730 -3.8733 -1.6236
H(9) -5.1165 -3.1858 -3.6642
C(11) -4.9342 -1.5002 -2.3070
C(12) -6.1015 -0.6153 -1.8901
C(13) -4.2544 -0.9016 -3.5313
C(14) -3.9321 -1.5895 -1.1636
H(15) -5.0197 -4.3820 0.4714
H(16) -5.0088 -2.5866 0.0958
H(17) -7.2996 -4.5759 -0.3880
H(18) -7.2214 -3.2232 0.8485
H(19) -8.5970 -2.6630 -1.1828
H(20) -7.1665 -1.5498 -0.9020
H(21) -7.3647 -3.8516 -2.9271
H(22) -7.3270 -2.0495 -3.2667
H(23) -5.1674 -4.9074 -1.9110
H(24) -3.7657 -3.7608 -1.6199
H(34) -7.0463 -1.2022 -1.9323
H(35) -5.9377 -0.2511 -0.8512
H(36) -6.1736 0.2537 -2.5818
H(37) -4.2988 -1.6280 -4.3734
H(38) -4.7769 0.0367 -3.8235
H(39) -3.1911 -0.6761 -3.2919
H(40) -3.8189 -2.6516 -0.8509
H(41) -2.9476 -1.1961 -1.5023
H(42) -4.2974 -0.9863 -0.3025

 

 

This was minimised to give an energy of 18.2721 kcal/mol, sadly the molecular mechanics software I used got stuck in a local minimum. I repeated the experiment using a starting model with the tert-butyl in the equatorial position and I got an energy of 13.3037 kcal/mol which is about 5 kcal per mole lower.

The cyclohexane with the equatorial tert-butyl has the following atomic coordinates.

30      
XYZ file : equatorial tert-butyl   cyclohexane
C -4.3929 0.5164 2.4518
C -5.1581 1.8367 2.3054
C -4.9586 2.4064 0.8962
C -5.3949 1.3918 -0.1722
C -4.6334 0.0543 -0.0517
C -4.8260 -0.4946 1.3784
C -4.9532 -0.9702 -1.1842
C -4.5813 -0.3826 -2.5668
C -6.4424 -1.3726 -1.2199
C -4.1128 -2.2576 -1.0089
H -4.5680 0.0910 3.4693
H -3.2972 0.7091 2.3633
H -6.2450 1.6629 2.4898
H -4.8063 2.5707 3.0692
H -5.5430 3.3515 0.7863
H -3.8839 2.6681 0.7473
H -6.4904 1.2165 -0.0663
H -5.2285 1.8590 -1.1697
H -3.5446 0.2969 -0.1512
H -5.8966 -0.7555 1.5444
H -4.2298 -1.4229 1.5350
H -5.2341 0.4691 -2.8568
H -3.5253 -0.0302 -2.5889
H -4.6936 -1.1383 -3.3767
H -7.1061 -0.5043 -1.4246
H -6.6363 -2.1181 -2.0241
H -6.7725 -1.8372 -0.2651
H -3.0288 -2.0248 -0.9058
H -4.4262 -2.8507 -0.1221
H -4.2219 -2.9409 -1.8812
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