Table 1 - Some Characteristic Signals of Bis-Benzimidazolium Salts in NMR Spectroscopy

Tables

Table 1 - Some characteristic signals of bis-benzimidazolium salts in NMR Spectroscopy.

1HNMR (δ ppm) /
CH2-R / N-CH2-R / N-CH2-Ar / NCHN
Propyl / 4.50 / 5.79 / 9.88
i-Propyl / 5.05 / 5.75 / 10.03
Butyl / 4.50 / 5.75 / 9.83
Pent-2-yl / 4.96 / 5.40 / 10.16
Benzyl / 5.74 / 5.78 / 10.18
Heptyl / 4.54 / 5.82 / 10.27
13CNMR(δ ppm) /
C-R / N-C-R / N-C-Ar / NCN
Propyl / 48.38 / 49.83 / 142.41
i-Propyl / 50.65 / 51.70 / 141.80
Butyl / 47.51 / 50.83 / 143.20
Pent-2-yl / 50.70 / 55.58 / 143.86
Benzyl / 51.11 / 51.34 / 142.30
Heptyl / 49.85 / 54.37 / 143.08

Table 2 -Crystal data and structure refinement details for compounds 10 and 13.

10.Br / 13.PF6
Formula / C36H32Br2N4 / C28H32F12N4P2
Formula Weight / 680.48 / 714.52
Crystal System / Triclinic / Monoclinic
Space group / P ī / Cc
a, b, c [Å] / 11.0707(3), 11.3028(3), 14.8929(3) / 16.2520(9), 12.0683(7), 16.2980(9)
α, β, ϒ [deg] / 84.963(1), 75.975(1), 87.924(1) / 90, 103.064(10), 90
V [Ang**3] / 1800.80(8) / 3152.2(3)
Z
D(calc)[g/cm**3]
Mu(MoKa)[/mm]
F(000)
Crystal Size[mm]
Temperature (K)
Radiation [Å]
θ Min – Max [Deg]
Dataset
Tot.; Uniq. Data
R(int)
Nref;Npar
R, wR2, S / 2
1.255
2.278
692
0.56 × 0.45 × 0.29
90(2)
MoKa 0.71073
1.41 – 28.95
-15:15; -15:15; -20 :20
33351
0.0308
9480; 379
0.0472, 0.1376, 1.076 / 4
1.506
0.236
1464
0.58×0.36 × 0.30
293(2)
MoKa 0.71073
2.11 – 30.070
-23:23; -16:16; -22:22
32572
0.0225
2023; 585
0.0226, 0.1293, 1.029

Table 3 -Selected bond lengths and angles of salt 10.2Br.

C6-C7 / 1.513(4) / C15-C16 / 1.515(4) / N3-C23 / 1.331(3)
C7-N1 / 1.481(3) / C16-C21 / 1.392(4) / C23-N4 / 1.332(4)
N1-C8 / 1.330(4) / C21-C20 / 1.383(4) / N4-C30 / 1.465(4)
N2-C8 / 1.339(4) / C20-C22 / 1.516(4) / C30-C31 / 1.511(4)
C15-N2 / 1.478(3) / C22-N3 / 1.464(3) / C21-H21 / 0.9500
C6-C7-N1 / 112.0(2) / C20-C22-N3 / 110.7(2)
C7-N1-C8 / 124.5(2) / C22-N3-C23 / 126.1(2)
N1-C8-N2 / 110.0(3) / N3-C23-N4 / 109.9(2)
C8-N2-C15 / 125.0(2) / C23-N4-C30 / 125.6(2)
N2-C15-C16 / 110.3(2) / N4-C30-C31 / 111.9(3)

Table 4 - Selected bond lengths and angles of salt 13.2PF6.

C2-C3 / 1.466(7) / C11-C12 / 1.516(3) / N3-C25 / 1.317(3)
C3-N2 / 1.508(4) / C12-C17 / 1.382(2) / C25-N4 / 1.338(3)
N2-C4 / 1.325(4) / C17-C16 / 1.384(2) / N4-C26 / 1.470(3)
C4-N1 / 1.321(3) / C16-C18 / 1.509(3) / C26-C27 / 1.484(6)
N1-C11 / 1.468(3) / C18-N3 / 1.474(2) / P1-F1 / 1.506(8)
C2-C3-N2 / 112.4(4) / C16-C18-N3 / 112.19(15)
C3-N2-C4 / 132.4(2) / C18-N3-C25 / 126.18(18)
N2-C4-N1 / 111.0(2) / N3-C25-N4 / 110.81(18)
C4-N1-C11 / 127.0(2) / C25-N4-C26 / 107.9(9)
N1-C11-C12 / 111.95(16) / N4-C26-C27 / 113.9(3)

Table 5 - IC50 Values of selected Compounds.

Sample Codes / IC50Value
8.2Br / 0.2 μM
9.2PF6 / 4.1 μM
10.2Br / 0.1 μM
11.2PF6 / 8.7 μM
12.2Br / 1.1 μM
13.PF6 / 17.6 μM
5-FU / 19.2 μM