Research Article
Spectroscopic Investigations and DFT Calculations on 3-(Diacetylamino)-2-ethyl-3H-quinazolin-4-one
Table 1
Experimental and calculated geometric parameters of compound 2 (figures in bold relate to parameters discussed in the text).
| Geometric parameters | Experimental values | Calculated values | B3LYP/6-311++G(d,p) | M06-2X/6-311++G(d,p) |
| Bond lengths (Å) | | | | C1–C2 | 1.458 | 1.461 | 1.462 | C1–O14 | 1.216 | 1.216 | 1.209 | C1–N35 | 1.406 | 1.422 | 1.411 | C2–C3 | 1.399 | 1.409 | 1.402 | C2–C6 | 1.403 | 1.403 | 1.399 | C3–C7 | 1.402 | 1.407 | 1.403 | C3–N13 | 1.398 | 1.387 | 1.389 | C4–N13 | 1.286 | 1.286 | 1.280 | C4–C15 | 1.499 | 1.509 | 1.505 | C4–N35 | 1.400 | 1.401 | 1.397 | H5–C6 | 0.93 | 1.083 | 1.084 | C6–C9 | 1.375 | 1.383 | 1.380 | C7–C8 | 1.372 | 1.384 | 1.381 | C7–H10 | 0.93 | 1.083 | 1.083 | C8–C9 | 1.387 | 1.405 | 1.403 | C8–H11 | 0.93 | 1.084 | 1.084 | C9–H12 | 0.93 | 1.084 | 1.083 | C15–H16 | 0.97 | 1.096 | 1.095 | C15–H17 | 0.97 | 1.095 | 1.095 | C15–C18 | 1.515 | 1.528 | 1.522 | C18–H19 | 0.96 | 1.091 | 1.090 | C18–H20 | 0.96 | 1.093 | 1.091 | C18–H21 | 0.96 | 1.090 | 1.089 | N22–C23 | 1.422 | 1.442 | 1.433 | N22–C29 | 1.417 | 1.421 | 1.416 | N22–N35 | 1.401 | 1.395 | 1.383 | C23–O24 | 1.201 | 1.207 | 1.201 | C23–C25 | 1.490 | 1.503 | 1.499 | C25–H26 | 0.96 | 1.091 | 1.089 | C25–H27 | 0.96 | 1.090 | 1.089 | C25–H28 | 0.96 | 1.089 | 1.088 | C29–O30 | 1.201 | 1.208 | 1.201 | C29–C31 | 1.496 | 1.511 | 1.508 | C31–H32 | 0.96 | 1.092 | 1.092 | C31–H33 | 0.96 | 1.092 | 1.092 | C31–H34 | 0.96 | 1.088 | 1.087 | | | 0.982 | 0.9799 | Bond angles () | | | | C2–C1–O14 | 126.6 | 126.5 | 126.6 | C2–C1–N35 | 112.9 | 113.1 | 112.8 | O14–C1–N35 | 120.5 | 120.4 | 120.5 | C1–C2–C3 | 119.3 | 119.3 | 119.3 | C1–C2–C6 | 120.2 | 120.1 | 119.8 | C3–C2–C6 | 120.4 | 120.6 | 120.9 | C2–C3–C7 | 118.9 | 118.8 | 118.7 | C2–C3–N13 | 122.9 | 122.6 | 122.8 | C7–C3–N13 | 118.1 | 118.6 | 118.4 | N13–C4–C15 | 121.5 | 120.7 | 121.1 | N13–C4–N35 | 121.7 | 121.9 | 122.3 | C15–C4–N35 | 116.8 | 117.3 | 116.5 | C2–C6–H5 | 120.3 | 118.6 | 118.5 | C2–C6–C9 | 119.5 | 119.8 | 119.6 | H5–C6–C9 | 119.9 | 121.6 | 121.9 | C3–C7–C8 | 119.8 | 120.1 | 120.1 | C3–C7–H10 | 120.1 | 118.3 | 118.1 | C8–C7–H10 | 120.1 | 121.6 | 121.8 | C7–C8–C9 | 121.2 | 120.7 | 120.9 | C7–C8–H11 | 119.4 | 119.6 | 119.6 | C9–C8–H11 | 119.9 | 119.6 | 119.5 | C6–C9–C8 | 120.1 | 119.9 | 119.8 | C6–C9–H12 | 119.9 | 120.2 | 120.2 | C8–C9–H12 | 119.9 | 119.9 | 119.9 | C3–N13–C4 | 121.7 | 119.4 | 118.7 | C4–C15–H16 | 108.9 | 109.0 | 108.8 | C4–C15–H17 | 108.9 | 107.8 | 107.5 | C4–C15–C18 | 113.3 | 113.7 | 112.7 | H16–C15–H17 | 107.7 | 105.7 | 106.1 | H16–C15–C18 | 108.9 | 110.1 | 110.8 | H17–C15–C18 | 108.9 | 110.1 | 110.6 | C15–C18–H19 | 109.5 | 111.4 | 110.9 | C15–C18–H20 | 109.5 | 109.5 | 109.7 | C15–C18–H21 | 109.5 | 111.1 | 110.7 | H19–C18–H20 | 109.5 | 108.6 | 108.9 | H19–C18–H21 | 109.5 | 107.5 | 107.6 | H20–C18–H21 | 109.5 | 108.6 | 108.9 | C23–N22–C29 | 127.8 | 126.9 | 127.1 | C23–N22–N35 | 114.0 | 114.1 | 114.0 | C29–N22–N35 | 117.2 | 118.1 | 117.8 | N22–C23–O24 | 118.4 | 117.9 | 117.8 | N22–C23–C25 | 118.4 | 118.8 | 118.4 | O24–C23–C25 | 123.3 | 123.4 | 123.8 | C23–C25–H26 | 109.5 | 111.1 | 110.7 | C23–C25–H27 | 109.5 | 111.2 | 110.7 | C23–C25–H28 | 109.5 | 106.9 | 106.7 | H26–C25–H27 | 109.5 | 106.6 | 106.9 | H26–C25–H28 | 109.5 | 110.5 | 110.8 | H27–C25–H28 | 109.5 | 110.7 | 110.9 | N22–C29–O30 | 120.5 | 120.9 | 121.1 | N22–C29–C31 | 116.7 | 116.3 | 115.5 | O30–C29–C31 | 122.8 | 122.9 | 123.4 | C29–C31–H32 | 109.5 | 112.2 | 111.5 | C29–C31–H33 | 109.5 | 110.2 | 109.8 | C29–C31–H34 | 109.5 | 107.3 | 107.3 | H32–C31–H33 | 109.5 | 108.1 | 108.3 | H32–C31–H34 | 109.5 | 109.6 | 110.0 | H33–C31–H34 | 109.5 | 109.6 | 109.9 | C1–N35–C4 | 124.5 | 123.6 | 123.9 | C1–N35–N22 | 116.1 | 115.9 | 115.9 | C4–N35–N22 | 119.2 | 119.8 | 119.4 | | | 0.9596 | 0.9599 |
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