1. Seol Lee, YongJae Cho and Kee Hag Lee*
Supplementary Materials
Five Regioisomers of Dimethyl Dodecahedrane Derivatives: a Hybrid DFT B3LYP Study
Seol Lee, YongJae Cho and Kee Hag Lee*
Department of Chemistry and Nanoscale Sciences and Technology Institute, Wonkwang University, Iksan, Jeonbuk 54538, R.O.K.
Figures S1-S5. The distance between the two methyl groups of Five C20H18Me2 isomers Table S1. Relative energies (kJ/mol) of five regioisomers. All calculations were performed using the optimized B3LYP/6-31G(d,p) geometries Table S2. Relative energies, zero point-corrected energies(ZPCE), enthalpies, and Gibbs free energies of five regioisomers. All calculations were performed using the optimized B3LYP/6-31G(d,p) geometries (unit: kJ/mol) Table S3. Relative Energies(kJ/mol) with Zero Point Energy-corrected to the optimized B3LYP/6-31G(d,p) geometries

2. cis-1 b3lyp/6-31g(d,p) opt=tight scf=tight int=ultrafine
2.883
Bond length
1.095
1.537
1.565
1.578
2.883
The distance between two methyl
Figure S1. The distance between the two methyl groups of cis-1 isomers is 2.883Å. Each color line represents the corresponding bond length (Å).

3. cis-2 b3lyp/6-31g(d,p) opt=tight scf=tight int=ultrafine
1.562
1.563
1.564
4.320
Bond length
1.096
1.535
1.562~1.564
4.320
Figure S2. The distance between the two methyl groups of cis-2 isomers is 4.320Å. Each color line represents the corresponding bond length (Å).

4. eq b3lyp/6-31g(d,p) opt=tight scf=tight int=ultrafine
6.103
1.563
Bond length
1.095
1.537
1.563~1.564
6.103
1.564
1.564
1.564
1.564
1.563
Figure S3. The distance between the two methyl groups of eq isomers is 6.103Å. Each color line represents the corresponding bond length (Å).

5. trans-1 b3lyp/6-31g(d,p) opt=tight scf=tight int=ultrafine
Bond length
1.096
1.535
1.564
7.484
7.484
Figure S4. The distance between the two methyl groups of trans-1 isomers is 7.484Å. Each color line represents the corresponding bond length (Å).

6. trans-2 b3lyp/6-31g(d,p) opt=tight scf=tight int=ultrafine
6.992
Bond length
1.096
1.535
1.564
6.992
Figure S5. The distance between the two methyl groups of trans-2 isomers is 6.992Å. Each color line represents the corresponding bond length (Å).

7. SP with empirical dispersion (D3)
Table S1. Relative energies (kJ/mol) of five regioisomers. All calculations were performed using the optimized B3LYP/6-31G(d,p) geometries
Isomers
Opt
SP with empirical dispersion (D3)
Opt with D3
cis-1
10.9
8.9
8.8
cis-2
0.3
-0.3
-0.5 Eq
0.1
0.0
-0.1
trans-2
0.2
trans-1
Here Opt = a geometry optimization; SP = a single-point energy calculation; D3 = functionals including empirical dispersion with Grimme’s D3 dispersion scheme.

8. Table S2. Relative energies, zero point-corrected energies(ZPCE), enthalpies, and Gibbs free energies of five regioisomers. All calculations were performed using the optimized B3LYP/6-31G(d,p) geometries (unit: kJ/mol)
isomers
rel. E
rel. ZPCE
rel. ΔH
rel. ΔG
rel. E(SP with D3)
cis-1
10.9
11.7
0.3
0.9
8.9
cis-2
0.2
-0.3
-0.5 eq
0.1
0.0
-0.2
trans-2
-0.4
-0.7
trans-1

9. SP with D3, empirical Dispersion
Table S3. Relative Energies(kJ/mol) with Zero Point Energy-corrected to the optimized B3LYP/6-31G(d,p) geometries
isomers
B3LYP/6-31G(d,p)
M062X/6-31G(d,p)
PBE/6-31G(d,p)
B98/ 6-31G (d,p)
B97D3/ G (d,p)
MP2/def2-TZVPP
OPT
SP with D3, empirical Dispersion SP
cis-1
11.74
9.78
8.02
7.93
9.56
9.36
10.96
9.16
10.31
cis-2
0.24
-0.36
-0.42
-0.52
0.10
-0.38
0.12
-0.70
1.54 eq
0.03
0.00
0.02
-0.01
0.05
0.01
0.08
-0.22
1.80
trans-2
0.07
-0.37
1.94
trans-1

10. Figure S1.
Relative Energies(kJ/mol) with Zero Point Energy-corrected to the optimized B3LYP/6-31G(d,p) geometries