Research Article
Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine
Table 1
Relative energiesa (kcal/mol), binding lengths (Å), and dihedral angle (°) of the low-lying isomers of the bis-cycloaddition.
| | | 4-Trans | 4-Cis |
| | ΔE (kcal/mol) | 00 | 12 | | C51-N1 | 1.413 | 1.430 | | N63-C2 | 1.502 | 1.521 | | C10-N28 | 1.489 | 1.521 | | C26-N15 | 1.385 | 1.429 | | C7-C2 | 1.536 | 1.537 | | C7-C10 | 1.552 | 1.537 | | N63-N62 | 1.367 | 1.374 | | N63-C64 | 1.407 | 1.420 | | N28-N27 | 1.379 | 1.374 | | N28-C29 | 1.397 | 1.420 | | C73-Cl50 | 1.759 | 1.758 | | C38-Cl39 | 1.759 | 1.758 | | C3-C2-C7-C10 | 54.84 | 67.20 | | C11-C10-C7-C2 | 162.13 | −67.42 | | N63-C2-C7-C10 | 0.30 | −170.16 | | N28-C10-C7-C2 | −70.01 | 170.00 |
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aCalculated according to 4-trans whose E is −2749.107545 ua at B3LYP/6-31G(d).
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