Table 1. Optimized Geometric Parametersa of Fluorene (FL), trans-AzoFL, and cis-AzoFL in the Ground State Calculated at B3LYP/6-31+G(d,p) and AM1 Methods.
| FL |
trans-AzoFL |
cis-AzoFL |
||||
|---|---|---|---|---|---|---|
| parametersa | AM1 | DFTb | AM1 | DFTb | AM1 | DFTb |
| N=N | 1.231 | 1.262 | 1.204 | 1.252 | ||
| C–N | 1.436 | 1.414 | 1.442 | 1.433 | ||
| C1–C2 | 1.403 | 1.401 | 1.421 | 1.407 | 1.417 | 1.406 |
| C2–C3 | 1.392 | 1.401 | 1.407 | 1.412 | 1.405 | 1.408 |
| C3–C4 | 1.402 | 1.398 | 1.399 | 1.390 | 1.398 | 1.394 |
| C4–C11 | 1.385 | 1.398 | 1.383 | 1.403 | 1.384 | 1.400 |
| C5–C12 | 1.385 | 1.398 | 1.385 | 1.399 | 1.385 | 1.399 |
| C5–C6 | 1.402 | 1.398 | 1.402 | 1.397 | 1.402 | 1.397 |
| C6–C7 | 1.392 | 1.401 | 1.392 | 1.402 | 1.392 | 1.401 |
| C7–C8 | 1.403 | 1.401 | 1.403 | 1.401 | 1.408 | 1.401 |
| C8–C13 | 1.382 | 1.392 | 1.382 | 1.392 | 1.382 | 1.392 |
| C1–C10 | 1.429 | 1.392 | 1.378 | 1.388 | 1.379 | 1.388 |
| C11–C12 | 1.461 | 1.470 | 1.460 | 1.466 | 1.461 | 1.468 |
| C12–C13 | 1.429 | 1.411 | 1.429 | 1.413 | 1.429 | 1.412 |
| C9–C10 | 1.504 | 1.516 | 1.505 | 1.515 | 1.505 | 1.516 |
| C9–C13 | 1.504 | 1.516 | 1.504 | 1.516 | 1.504 | 1.516 |
| C10–C11 | 1.429 | 1.411 | 1.429 | 1.411 | 1.428 | 1.413 |
| C1–H | 1.099 | 1.087 | 1.100 | 1.086 | 1.101 | 1.087 |
| C2–H | 1.100 | 1.086 | ||||
| C3–H | 1.100 | 1.086 | 1.102 | 1.084 | 1.102 | 1.086 |
| C4–H | 1.110 | 1.086 | 1.100 | 1.087 | 1.099 | 1.086 |
| C5–H | 1.110 | 1.086 | 1.099 | 1.086 | 1.099 | 1.086 |
| C6–H | 1.100 | 1.086 | 1.100 | 1.086 | 1.100 | 1.086 |
| C7–H | 1.100 | 1.086 | 1.100 | 1.086 | 1.100 | 1.086 |
| C8–H | 1.099 | 1.087 | 1.099 | 1.087 | 1.098 | 1.087 |
| C9–H | 1.119 | 1.098 | 1.120 | 1.098 | 1.119 | 1.098 |
| C9–H | 1.119 | 1.098 | 1.120 | 1.098 | 1.119 | 1.098 |
| N1–C2–C3 | 124.9 | 124.6 | 122.5 | 123.0 | ||
| C2–N1=N2 | 119.7 | 115.5 | 129.4 | 124.4 | ||
| N1=N2–C2′ | 119.7 | 115.5 | 129.4 | 124.4 | ||
| C2–C3–C4 | 120.9 | 120.6 | 121.1 | 120.3 | 121.1 | 120.3 |
| C1–C2–C3 | 120.9 | 120.5 | 119.8 | 120.2 | 120.0 | 120.3 |
| C10–C1–C2 | 118.7 | 119.1 | 118.7 | 119.3 | 118.6 | 119.1 |
| C3–C4–C11 | 118.6 | 118.9 | 119.1 | 119.4 | 118.9 | 119.4 |
| C4–C11–C10 | 120.5 | 120.4 | 120.2 | 120.3 | 120.2 | 120.1 |
| C1–C10–C11 | 120.5 | 120.5 | 121.1 | 120.4 | 110.0 | 120.6 |
| C9–C10–C11 | 110.5 | 110.0 | 110.0 | 110.0 | 110.0 | 110.0 |
| C9–C13–C12 | 110.5 | 110.0 | 110.1 | 110.0 | 110.1 | 110.1 |
| C10–C9–C13 | 103.3 | 102.8 | 103.3 | 102.7 | 103.3 | 102.7 |
| C10–C11–C12 | 108.3 | 108.6 | 108.4 | 108.7 | 108.4 | 108.6 |
| C13–C12–C11 | 108.3 | 108.6 | 108.3 | 108.5 | 108.3 | 108.5 |
| C12–C5–C6 | 118.6 | 118.9 | 118.6 | 118.8 | 118.6 | 118.9 |
| C5–C6–C7 | 120.9 | 120.6 | 120.9 | 120.6 | 120.9 | 120.7 |
| C6–C7–C8 | 120.9 | 120.5 | 120.9 | 120.6 | 120.9 | 120.6 |
| C7–C8–C13 | 118.7 | 119.1 | 118.7 | 119.0 | 118.7 | 119.0 |
| C8–C13–C12 | 120.5 | 120.5 | 120.4 | 120.4 | 120.4 | 120.4 |
| C13–C12–C5 | 120.5 | 120.4 | 120.5 | 120.5 | 120.5 | 120.5 |
| C1–C2–N1 | 115.3 | 115.2 | 117.3 | 116.1 | ||
| C3–C2–N1 | 124.9 | 124.6 | 122.5 | 123.0 | ||
| C2N1N2C2′ | 179.3 | –179.99 | 2.3 | 10.9 | ||
| C3C2N1N2 | –15.7 | 0.01 | 46.9 | 48.1 | ||
a
Bond lengths in angstroms and bond angles and dihedral angles in degrees.
b
B3LYP/6-31+G(d,p).