## 3 Results
### Computational Studies
#### 3.3.1 Geometry Optimization
The same is said for the Q-TNCQ complex with N(39) H-C(4)(2.13 A) and N(38) H-C(14)(2.26A). Mulliken atomic charges of quinine are provided in (Figure 8). \begin{table}
\begin{tabular}{c c c c} \hline \multirow{2}{*}{**No.**} & \multicolumn{3}{c}{**Chemical Shifts (ppm)**} & \multirow{2}{*}{**Assignment**} \\ \cline{2-3}  & **Quinine** & & **Q-DDQ Charge Transfer Complex** \\ \hline
1 & & 174.32 & DDQ \\ \hline
2 & & 172.02 & DDQ \\ \hline
3 & & 171.09 & DDQ \\ \hline
4 & & 161.89 & DDQ \\ \hline
5 & & 159.48 & DDQ \\ \hline
6 & 158.90 & 159.45 & 6\({}^{\prime}\) \\ \hline
7 & 147.74 & 150.86 & 4\({}^{\prime}\) \\ \hline
8 & 145.98 & 144.66 & 2\({}^{\prime}\) \\ \hline
9 & 144.95 & 138.95 & 10\({}^{\prime}\) \\ \hline
10 & 139.66 & 136.24 & 10 \\ \hline
11 & 132.03 & 129.24 & 8\({}^{\prime}\) \\ \hline
12 & 126.57 & 126.78 & 9\({}^{\prime}\) \\ \hline
13 & 122.80 & 119.80 & 7\({}^{\prime}\) \\ \hline
14 & 119.72 & 116.33 & 3\({}^{\prime}\) \\ \hline
15 & 116.59 & 113.75 & 11 \\ \hline
16 & 101.74 & 102.88 & 5\({}^{\prime}\) \\ \hline
17 & & 101.70 & DDQ \\ \hline
18 & & 87.82 & DDQ \\ \hline
19 & 66.71 & 65.85 & 9 \\ \hline
20 & 60.58 & 58.77 & 8 \\ \hline
21 & 57.72 & 57.68 & 2 \\ \hline
22 & 54.66 & 53.03 & MeO \\ \hline
23 & 44.08 & 42.71 & 6 \\ \hline
24 & & 40.43 & DDQ \\ \hline
25 & 38.26 & 36.79 & 3 \\ \hline
26 & 28.28 & 26.67 & 4 \\ \hline
27 & 25.02 & 23.81 & 5 \\ \hline
28 & 18.71 & 17.63 & 7 \\ \hline \end{tabular}
\end{table} 
Table 4: \({}^{13}\)C NMR chemical shifts in ppm for quinine and quinine-DDQ charge transfer complex. Comparing the bond lengths between the free drug, the acceptors and their complexes reveals the lengthening of Quinine bonds of C(10)-N(3), N(3)-C(6) and N(3)-C(11) by 0.023A, 0.320A and 0.0180A at CT formation. In addition, the angle of C(6)-N(3)-C(11) varies by 3.346 A in the case of Q-DDQ. As for Q-TNCQ, a Q bond lengthening of C(10)-N(3), N(3)-C(6) and N(3)-C(11) by 0.0020, 0.1320 and 0.1830 A, respectively, is observed along with an angle reduction in C(6)-N(3)-C(11) by 4.437 A. \begin{table}
\begin{tabular}{c c c c} \hline \hline \multirow{2}{*}{**No.**} & \multicolumn{3}{c}{**Chemical Shifts (ppm)**} \\ \cline{2-3}  & **Quinine** & **Quinine-TCNQ Charge Transfer Complex** & **Assignments** \\ \hline
1 & & 161.94 & TCNQ \\ \hline
2 & 158.90 & 158.06 & 6\({}^{\prime}\) \\ \hline
3 & & 153.08 & TCNQ \\ \hline
4 & 147.74 & 146.84 & 4\({}^{\prime}\) \\ \hline
5 & 145.98 & 146.26 & 2\({}^{\prime}\) \\ \hline
6 & 144.95 & 142.94 & 10\({}^{\prime}\) \\ \hline
7 & 139.66 & 138.99 & 10 \\ \hline
8 & 132.03 & 130.66 & 8\({}^{\prime}\) \\ \hline
9 & & 129.45 & TCNQ \\ \hline
10 & & 125.82 & TCNQ \\ \hline
11 & 126.57 & 125.78 & 9\({}^{\prime}\) \\ \hline
12 & & 124.66 & TCNQ \\ \hline
13 & & 124.02 & TCNQ \\ \hline
14 & 122.80 & 122.42 & 7\({}^{\prime}\) \\ \hline
15 & & 121.11 & TCNQ \\ \hline
16 & 119.72 & 119.15 & 3\({}^{\prime}\) \\ \hline
17 & & 118.07 & TCNQ \\ \hline
18 & 116.59 & 116.19 & 11 \\ \hline
19 & & 114.53 & TCNQ \\ \hline
20 & & 102.10 & TCNQ \\ \hline
21 & 101.74 & 102.03 & 5\({}^{\prime}\) \\ \hline
22 & 66.71 & 65.54 & 9 \\ \hline
23 & 60.58 & 58.99 & 8 \\ \hline
24 & 57.72 & 57.17 & 2 \\ \hline
25 & 54.66 & 52.89 & MeO \\ \hline
26 & 44.08 & 42.69 & 6 \\ \hline
27 & & 40.43 & TCNQ \\ \hline
28 & 38.26 & 36.77 & 3 \\ \hline
29 & 28.28 & 26.72 & 4 \\ \hline
30 & & 25.48 & TCNQ \\ \hline
31 & 25.02 & 23.84 & 5 \\ \hline
32 & 18.71 & 17.62 & 7 \\ \hline \hline \end{tabular}
\end{table} 
Table 5: \({}^{13}\)C chemical shifts in ppm for quinine and quinine-TCNQ charge transfer complex. Figure 8: _Cont._  
Figure 7: Optimized geometry of Quinine. Conversely, a decrease of 0.0049 A and 0.0048A in the bond length of C(30)-O(31) and C(27)-O(32) is observed in the DDQ moiety following the lengthening of C = O groups and the formation of double bonds. From the previous results and the HOMO-LUMO energy gap values, we conclude that the Q-DDQ and Q-TNCQ complexes belong either to the semiconductor or conductor classes.