Table 2. Structural and optical properties of C8-aryl-dG nucleoside adducts.
| Adduct | Eanti-Esyna | χ/θb | μ | λex,λemc (Φfld) | λex,λem (Φfl) | λex,λem (Φfl) |
|---|---|---|---|---|---|---|
| kJ mol−1 | Degrees | Debye | H2Oe | CH3CN | CHCl3 | |
| FurGf | 19.3 | 50.1/343.8 | 4.3 | 292, 384 (0.49) | 292, 371 (0.18) | 298, 366 (0.03) |
| PhG | 25.1 | 66.8/41.2 | 4.8 | 277, 395 (0.44) | 292, 384 (0.49) | 289, 373 (0.22) |
| CNPhGg | 26.9 | 68.4/37.9 | 8.9 | 308, 468 (0.04) | 327, 454 (0.43) | 325, 424 (0.35) |
| QG | 29.5 | 52.2/305.6 | 4.3 | 313, 407 (0.03) | 315, 384,510 (0.05) | 318, 468 (0.19) |
aOptimized at the B3LYP/6–31G(d) level, with values corresponding to a syn-conformation with a relative energy of 0 kJ mol−1.
bThe dihedral angle χ (O4′C1′N9C4) defines the glycosidic bond orientation to be anti when χ = 180 ± 90º or syn when χ = 0 ± 90º; θ (∠(N9C8C10C11) for PhG, CNPhG and QG and ∠(N9C8C10O11) for FurG) defines the degree of twist between the nucleobase and the C8-aryl group.
cExcitation and emission maxima in nm.
dDetermined using the comparative method with quinine bisulfate in 0.5 M H2SO4 (Φfl = 0.55).
eDetermined in aqueous 10 mM MOPS buffer, pH 7, μ = 0.1 M NaCl.
fOptical data in H2O and energy calculations for FurG taken from (49).
gOptical data in H2O and energy calculations for CNPhdG taken from (50).