3.2 Results in Vacuo
80 conformers were identified, and the frequency calculations confirm that they
correspond to true minima. The relative energies of selected calculated conformers
of JZM in vacuo and in the three solvents considered are reported in Table 2.
Table 2 Relative energies of the selected conformers of jozimine A 2 shown in Fig. 3. HF/6-31G
(d,p) and DFT/B3LYP/6-31+G(d,p) results in vacuo and in the solvents considered, respectively
denoted as HF and DFT in the columns’ headings. The results in vacuo are from full optimization
calculations; the results in solution are from single point PCM calculations on the
in-vacuo-optimized geometries. The conformers are listed in order of increasing relative energies
in the HF results in vacuo
Conformer
Relative energy (kcal/mol)
HF
DFT
vac
chlrf
actn
aq
vac
chlrf
actn
aq
a-b-e-f-g-h-p-v-x
0.000
0.000
0.000
0.112
0.000 0.000
0.000
0.095
a-b-e-f-g-h-q-v-x
0.743
0.467
0.278
0.020
0.608 0.404
0.320
0.000
a-b-e-f-g-h-q-t-x
0.793
0.591
0.303
0.243
0.606 0.411
0.290
0.058
a-b-e-f-g-h-q-v-y
1.463
0.637
0.618
0.000
1.202 0.777
0.567
0.005
a-b-e-f-g-h-p-t-x
1.466
0.920
0.707
0.075
1.180 0.825
0.578
0.187
a-b-f-h-q-v-x
5.783
5.411
3.856
1.772
5.634 4.645
3.970
1.860
a-d-e-f-g-h-q-v-x
5.857
5.469
5.429
3.921
5.944 5.799
−
a
−
a
b-c-e-f-g-h-q-t-x
5.934
5.759
5.547
3.902
5.990 5.840
5.679
4.132
a-b-e-g-q-t-x
5.962
4.497
4.003
1.987
5.770 4.757
4.121
1.900
b-c-e-f-g-h-p-v-x
6.209
5.756
5.725
4.095
6.267 6.053
5.902
4.341
a-d-e-f-g-h-p-v-x
6.209
5.756
5.725
4.095
6.267 6.053
5.897
4.375
a-b-e-g-p-v-x
6.269
5.549
4.132
2.037
6.028 4.978
4.266
2.160
a-b-f-h-p-v-x
6.269
4.914
4.192
2.096
6.028 5.004
−
a
2.134
a-b-e-g-v-y
6.476
5.168
4.123
1.625
6.202 −
a
−
a
1.819
a-b-f-h-v-y
6.476
5.157
4.037
1.706
6.202 4.917
4.289
1.813
a-b-e-g-p-t-x
6.552
5.316
4.308
1.969
6.204 5.008
4.295
1.999
a-b-f-h-p-t-x
6.552
5.194
4.294
1.945
6.204 5.021
4.278
1.959
c-d-e-f-g-h-p-v-x 11.627 11.590 11.467
8.363 11.508 11.728 11.623 8.798
a-d-e-g-p-t-x
11.682 10.404
9.397
5.723 11.568 10.460 9.692
6.632
a-b-q-v-y
11.899
9.483
7.954
3.038 11.602 −
a
−
a
3.878
a-b-p-t-x
12.096 10.142
8.111
3.817 11.684 9.638
8.295
4.437
c-d-f-h-p-v-x
15.532 14.858 14.216 10.362 15.508 15.181 14.688 10.984
c-d-f-h-q-v-x
15.687 14.974 14.302
3.432 15.648 15.128 14.575 −
a
b-c-q-v-y
16.262 13.764 12.531
6.784 16.266 14.080 12.760 7.637
a-d-q-v-y
16.262 13.982 12.425
6.961 16.266 14.099 12.753 7.714
c-d-q-v-y
20.097 18.547 17.013 11.069 20.169 18.675 17.585 11.609
c-d-p-t-x
20.432 18.889 17.427 11.707 20.216 18.933 18.027 12.417
a The calculation for this conformer did not converge in the given solvent
Computational Study of Jozimine A 2 , a Naphthylisoquinoline …
313
80 conformers were identified, and the frequency calculations confirm that they
correspond to true minima. The relative energies of selected calculated conformers
of JZM in vacuo and in the three solvents considered are reported in Table 2.
Table 2 Relative energies of the selected conformers of jozimine A 2 shown in Fig. 3. HF/6-31G
(d,p) and DFT/B3LYP/6-31+G(d,p) results in vacuo and in the solvents considered, respectively
denoted as HF and DFT in the columns’ headings. The results in vacuo are from full optimization
calculations; the results in solution are from single point PCM calculations on the
in-vacuo-optimized geometries. The conformers are listed in order of increasing relative energies
in the HF results in vacuo
Conformer
Relative energy (kcal/mol)
HF
DFT
vac
chlrf
actn
aq
vac
chlrf
actn
aq
a-b-e-f-g-h-p-v-x
0.000
0.000
0.000
0.112
0.000 0.000
0.000
0.095
a-b-e-f-g-h-q-v-x
0.743
0.467
0.278
0.020
0.608 0.404
0.320
0.000
a-b-e-f-g-h-q-t-x
0.793
0.591
0.303
0.243
0.606 0.411
0.290
0.058
a-b-e-f-g-h-q-v-y
1.463
0.637
0.618
0.000
1.202 0.777
0.567
0.005
a-b-e-f-g-h-p-t-x
1.466
0.920
0.707
0.075
1.180 0.825
0.578
0.187
a-b-f-h-q-v-x
5.783
5.411
3.856
1.772
5.634 4.645
3.970
1.860
a-d-e-f-g-h-q-v-x
5.857
5.469
5.429
3.921
5.944 5.799
−
a
−
a
b-c-e-f-g-h-q-t-x
5.934
5.759
5.547
3.902
5.990 5.840
5.679
4.132
a-b-e-g-q-t-x
5.962
4.497
4.003
1.987
5.770 4.757
4.121
1.900
b-c-e-f-g-h-p-v-x
6.209
5.756
5.725
4.095
6.267 6.053
5.902
4.341
a-d-e-f-g-h-p-v-x
6.209
5.756
5.725
4.095
6.267 6.053
5.897
4.375
a-b-e-g-p-v-x
6.269
5.549
4.132
2.037
6.028 4.978
4.266
2.160
a-b-f-h-p-v-x
6.269
4.914
4.192
2.096
6.028 5.004
−
a
2.134
a-b-e-g-v-y
6.476
5.168
4.123
1.625
6.202 −
a
−
a
1.819
a-b-f-h-v-y
6.476
5.157
4.037
1.706
6.202 4.917
4.289
1.813
a-b-e-g-p-t-x
6.552
5.316
4.308
1.969
6.204 5.008
4.295
1.999
a-b-f-h-p-t-x
6.552
5.194
4.294
1.945
6.204 5.021
4.278
1.959
c-d-e-f-g-h-p-v-x 11.627 11.590 11.467
8.363 11.508 11.728 11.623 8.798
a-d-e-g-p-t-x
11.682 10.404
9.397
5.723 11.568 10.460 9.692
6.632
a-b-q-v-y
11.899
9.483
7.954
3.038 11.602 −
a
−
a
3.878
a-b-p-t-x
12.096 10.142
8.111
3.817 11.684 9.638
8.295
4.437
c-d-f-h-p-v-x
15.532 14.858 14.216 10.362 15.508 15.181 14.688 10.984
c-d-f-h-q-v-x
15.687 14.974 14.302
3.432 15.648 15.128 14.575 −
a
b-c-q-v-y
16.262 13.764 12.531
6.784 16.266 14.080 12.760 7.637
a-d-q-v-y
16.262 13.982 12.425
6.961 16.266 14.099 12.753 7.714
c-d-q-v-y
20.097 18.547 17.013 11.069 20.169 18.675 17.585 11.609
c-d-p-t-x
20.432 18.889 17.427 11.707 20.216 18.933 18.027 12.417
a The calculation for this conformer did not converge in the given solvent
Computational Study of Jozimine A 2 , a Naphthylisoquinoline …
313