194
M. K. Bilonda and L. Mammino
Table 6 Relative energy (E correct , kcal/mol) corrected for ZPE and ZPE corrections (kcal/mol) for
the conformers of shuangancistrotectorine A Results from HF/6-31G(d,p) frequency calculations
Conformers
E correct
ZPE
correction
Conformers
E correct
ZPE
correction
1-a-b-g-h-i-u-q-v-x 0.000
653.177
9-a-d-g-h-i-u-q-v-x
4.745
652.993
2-a-b-g-h-i-u-q-t-y 1.068
653.027
10-a-d-g-h-i-u-q-t-x 5.429
652.986
3-a-b-g-h-i-u-p-v-y 1.055
653.038
11-b-c-g-h-i-u-q-t-x 5.429
652.986
4-a-b-g-h-i-u-q-t-x 1.800
653.073
12-b-c-g-h-i-u-q-t-y 5.457
652.897
5-b-c-g-h-i-u-p-v-y 4.604
652.914
13-c-d-g-h-i-u-p-v-y 7.657
652.826
6-a-d-g-h-i-u-q-t-y 4.275
652.948
14-c-d-g-h-i-u-q-t-x 8.498
652.922
7-a-d-g-h-i-u-p-v-y 4.604
652.914
15-c-d-g-h-i-u-q-v-x 9.078
652.885
8-b-c-g-h-i-u-q-v-x 4.744
652.993
16-c-d-g-h-i-u-q-t-y 8.080
652.845
The absolute energy of the lowest energy conformer (hartree) is −2633.861716/non-corrected and
−2632.820812/corrected
Table 7 Dipole moment of the calculated conformers of shuangancistrotectorine A HF/6-31G(d,p)
and (DFT/B3LYP/6-31+G(d,p) results in vacuo, respectively denoted as HF and DFT in the column
headings
Conformers
Dipole moment (D)
Conformers
Dipole moment (D)
HF
DFT
HF
DFT
1-a-b-g-h-i-u-q-v-x
0.054
0.250
9-a-d-g-h-i-u-q-v-x
4.235
4.160
2-a-b-g-h-i-u-q-t-y
2.270
2.350
10-a-d-g-h-i-u-q-t-x
3.970
4.131
3-a-b-g-h-i-u-p-v-y
2.777
3.137
11-b-c-g-h-i-u-q-t-x
3.970
4.130
4-a-b-g-h-i-u-q-t-x
2.301
2.874
12-b-c-g-h-i-u-q-t-y
5.333
5.105
5-b-c-g-h-i-u-p-v-y
2.733
3.083
13-c-d-g-h-i-u-p-v-y
2.733
0.255
6-a-d-g-h-i-u-q-t-y
2.733
3.083
14-c-d-g-h-i-u-q-t-x
0.278
0.236
7-a-d-g-h-i-u-p-v-y
4.149
4.255
15-c-d-g-h-i-u-q-v-x
2.820
2.541
8-b-c-g-h-i-u-q-v-x
4.235
4.160
16-c-d-g-h-i-u-q-t-y
2.000
1.807
orientation of the OH groups. Conformers with the two O–H···O IHBs and all the
C–H···O IHBs (the four lowest energy conformers) and conformers with the two
O–H···π IHBs and all the C–H···O IHBs (the four highest energy conformers) have
lower dipole moments, with the first lowest energy conformer having the lowest
value. Most of the conformers with one O–H···O IHB, one O–H···π IHB and all
the C–H···O IHBs have high dipole moments (with few exceptions). The mutual
orientation of the moieties also has considerable influence on the dipole moment.
Different orientations of the S and S’ units may cause 2-4 D difference in the dipole
moments, and different orientations of the isoquinoline and naphthalene moieties
within each unit may cause ≈2 D difference. The two conformers of a symmetric
pair have the same dipole moment.
M. K. Bilonda and L. Mammino
Table 6 Relative energy (E correct , kcal/mol) corrected for ZPE and ZPE corrections (kcal/mol) for
the conformers of shuangancistrotectorine A Results from HF/6-31G(d,p) frequency calculations
Conformers
E correct
ZPE
correction
Conformers
E correct
ZPE
correction
1-a-b-g-h-i-u-q-v-x 0.000
653.177
9-a-d-g-h-i-u-q-v-x
4.745
652.993
2-a-b-g-h-i-u-q-t-y 1.068
653.027
10-a-d-g-h-i-u-q-t-x 5.429
652.986
3-a-b-g-h-i-u-p-v-y 1.055
653.038
11-b-c-g-h-i-u-q-t-x 5.429
652.986
4-a-b-g-h-i-u-q-t-x 1.800
653.073
12-b-c-g-h-i-u-q-t-y 5.457
652.897
5-b-c-g-h-i-u-p-v-y 4.604
652.914
13-c-d-g-h-i-u-p-v-y 7.657
652.826
6-a-d-g-h-i-u-q-t-y 4.275
652.948
14-c-d-g-h-i-u-q-t-x 8.498
652.922
7-a-d-g-h-i-u-p-v-y 4.604
652.914
15-c-d-g-h-i-u-q-v-x 9.078
652.885
8-b-c-g-h-i-u-q-v-x 4.744
652.993
16-c-d-g-h-i-u-q-t-y 8.080
652.845
The absolute energy of the lowest energy conformer (hartree) is −2633.861716/non-corrected and
−2632.820812/corrected
Table 7 Dipole moment of the calculated conformers of shuangancistrotectorine A HF/6-31G(d,p)
and (DFT/B3LYP/6-31+G(d,p) results in vacuo, respectively denoted as HF and DFT in the column
headings
Conformers
Dipole moment (D)
Conformers
Dipole moment (D)
HF
DFT
HF
DFT
1-a-b-g-h-i-u-q-v-x
0.054
0.250
9-a-d-g-h-i-u-q-v-x
4.235
4.160
2-a-b-g-h-i-u-q-t-y
2.270
2.350
10-a-d-g-h-i-u-q-t-x
3.970
4.131
3-a-b-g-h-i-u-p-v-y
2.777
3.137
11-b-c-g-h-i-u-q-t-x
3.970
4.130
4-a-b-g-h-i-u-q-t-x
2.301
2.874
12-b-c-g-h-i-u-q-t-y
5.333
5.105
5-b-c-g-h-i-u-p-v-y
2.733
3.083
13-c-d-g-h-i-u-p-v-y
2.733
0.255
6-a-d-g-h-i-u-q-t-y
2.733
3.083
14-c-d-g-h-i-u-q-t-x
0.278
0.236
7-a-d-g-h-i-u-p-v-y
4.149
4.255
15-c-d-g-h-i-u-q-v-x
2.820
2.541
8-b-c-g-h-i-u-q-v-x
4.235
4.160
16-c-d-g-h-i-u-q-t-y
2.000
1.807
orientation of the OH groups. Conformers with the two O–H···O IHBs and all the
C–H···O IHBs (the four lowest energy conformers) and conformers with the two
O–H···π IHBs and all the C–H···O IHBs (the four highest energy conformers) have
lower dipole moments, with the first lowest energy conformer having the lowest
value. Most of the conformers with one O–H···O IHB, one O–H···π IHB and all
the C–H···O IHBs have high dipole moments (with few exceptions). The mutual
orientation of the moieties also has considerable influence on the dipole moment.
Different orientations of the S and S’ units may cause 2-4 D difference in the dipole
moments, and different orientations of the isoquinoline and naphthalene moieties
within each unit may cause ≈2 D difference. The two conformers of a symmetric
pair have the same dipole moment.