## 3 Results
### Computational Studies  
#### 3.3.1 Geometry Optimization  
The Quinine structure was optimized in the gas phase using the B3 LYP function along with the 6-311++G(d,p) basis set to confirm that the molecule has a minimum energy conformation allowing the acquisition of theoretical UV spectra. A comparison of these theoretical spectra with experimental results is depicted in Figure 7.  
The optimized structure of quinine (Figure 7) shows a rich conformational behavior. The most important degrees of freedom are the two torsional angles, \(\tau\)1: C17-C14-C12-C6 and \(\tau\)2: C14-C12-C6-N3, which determine the relative orientation of the quinoline moiety [26]. It should be noted that the methoxy substituent of the quinoline ring is one of the most stable conformations in a cis conformation [27]. \begin{table}
\begin{tabular}{c c c} \hline
**Quinine** & **Quinine-DDQ** & **Quinine-TCNQ** \\ \hline
1.45 (1H, t, \(J=10\) Hz, H4) & 1.50 (1H, t, \(J=10.0\) Hz, H4) & 1.50 (1H, t, \(J=10\) Hz, H4) \\ \hline
1.96 (1H, dt, \(J=10\), 3 Hz, H5a) & 1.91 (1H, dt, \(J=10.0\), 3.0, Hz, H5a) & 1.91 (1H, dt, \(J=10\), 2 Hz, H5a) \\
2.07 (1H, d, \(J=2\) Hz, H5b) & 2.56 (1H, sept., \(J=1.5\) Hz, H5b) & 2.56 (1H, sept., \(J=1.5\) Hz, H5b) \\ \hline
2.16-2.23 (2H, m, H7a,b) & 2.08-2.10 (2H, m, H7a,b) & 2.08-2.10 (2H, m H7a,b) \\ \hline
2.84 (1H, q, \(J=5\) Hz, H3) & 2.77 (1H, q, \(J=5\) Hz, H3) & 2.77 (1H, q, \(J=5\) Hz, H3) \\ \hline
3.17 (1H, ddd, \(J=10\), 5, 1.5 Hz, 6a) & 3.18 (1H, ddd, \(J=10\), 5, 1.5 Hz, H6a) & 3.18 (1H, ddd, \(J=10.5\), 5, 2 Hz, H6a) \\ \hline
3.26 (1H, dt, \(J=11.5\), 3.5 Hz, H6b) & 3.27 (1H, dt, \(J=11.5\), 3.5 Hz, H6b) & 3.27 (1H, dt, \(J=10.5\), 3.5 Hz, H6b) \\ \hline
3.56 (2H, ddd, \(J=12.5\), 8.5, 7.5 Hz, H2 ab) & 3.58 (1H, t, \(J=9\) Hz, H2a) & 3.58 (1H, ddd, \(J=12.5\), 8.5, 7.5 Hz, H2a) \\  & 3.68 (1H, t, \(J=6\) Hz, H2b) & 3.68 (1H, ddd, \(J=12.5\), 8.5, 7.5 Hz, H2b) \\ \hline
3.71 (3H, s OCH\({}_{3}\)) & 4.17 (3H, s OCH\({}_{3}\)) & 4.17 (3H, s OCH\({}_{3}\)) \\ \hline
4.33 (1H, t, \(J=10\) Hz, H8) & 4.05 (1H, t, \(J=10\) Hz, H8) & 4.05 (1H, t, \(J=8.5\) Hz, H8) \\ \hline
4.92 (1H, d, \(J=7.5\) Hz, H11) & 5.02 (1H, d, \(J=7.5\) Hz, H11) & 5.02 (1H, d, \(J=7.5\) Hz, H11) \\ \hline
5.07 (1H, \(J=12.5\) Hz, H11) & 5.14 (1H, \(J=12.5\) Hz, H11) & 5.14 (1H, \(J=12\) Hz, H11) \\ \hline
5.77 (1H, ddd, \(J=12.5\), 7, 5 Hz H10) & 5.85 (1H, ddd, \(J=12.5\), 7, 5 Hz, H10) & 5.85 (1H, ddd, \(J=12.7\), 5 Hz, H10) \\ \hline
6.37 (1H, br s OH) & 6.94 (1H, br s OH) & 6.94 (1H, br s OH) \\ \hline
6.56 (1H, s H9) & 6.55 (1H, dd, \(J=6.5\), 1.5 H9) & 6.55 (1H, d, \(J=3\) Hz, H9) \\ \hline
7.02 (1H, dd, \(J=6.5\), 1.5 H7\({}^{\prime}\)) & 7.79 (1H, dd, \(J=9\), 2 Hz, H7\({}^{\prime}\)) & 7.79 (1H, dd, \(J=6.5\), 2 Hz, H7\({}^{\prime}\)) \\ \hline
7.32 (1H, d, \(J=2\) Hz, H3\({}^{\prime}\)) & 7.96 (1H, d, \(J=4.0\) Hz, H3\({}^{\prime}\)) & 7.96 (1H, d, \(J=2\) Hz, H3\({}^{\prime}\)) \\ \hline
7.69 (1H, d, \(J=3.2\) Hz, H5\({}^{\prime}\)) & 8.09 (1H, m, H5\({}^{\prime}\)) & 8.10 (1H, d, \(J=3\) Hz, H5\({}^{\prime}\)) \\ \hline
7.72 (1H, d, \(J=6.5\) Hz, H8\({}^{\prime}\)) & 8.32 (1H, dd, \(J=9.5\), 4.7 Hz, H8\({}^{\prime}\)) & 8.32 (1H, d, \(J=6.5\) Hz, H8\({}^{\prime}\)) \\ \hline
8.67 (1H, d, \(J=3.2\) Hz, H2\({}^{\prime}\)) & 9.10 (1H, dd, \(J=4.0\), 1.0 Hz, H2\({}^{\prime}\)) & 9.10 (1H, d, \(J=3.2\) Hz, H2\({}^{\prime}\)) \\ \hline \end{tabular}
\end{table} 
Table 3: \({}^{1}\)H NMR chemical shifts in ppm for quinine and quinine-DDQ, and quinine-TCNQ charge-transfer complexes. A description of the **Mulliken** charges of quinine, DDQ and TNCQ are shown in Figure 8. The donor Quinine molecule approaches the DDQ and TNCQ acceptor molecules from the nitrogen atom of the quinoline ring. From (Table S1) we can deduce the transferred charge between quinine and (DDQ, TNCQ). Quinine has a tertiary amine of the quinuclidine subunit. As illustrated in Figure 8, the Q-DDQ complex structure is stabilized by two H bonds given by O(31) H-C(18)(2.04 A) and N(37) H-C(14)(2.17 A).