Substitution of the halogen atoms in α-halogenonitro compounds of the aliphatic series. 5. Use of the MNDO method to explain the behavior of the chlorine atom in the substitution reactions of chloronitroacetic acid derivatives
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The geometric parameters, bond orders, and charge distributions in the molecules of ethyl nitroacetate (I), ethyl chloronitroacetate (II), chloronitroacetamide (III), ethyl chloroacetate (IV), and the anions of ethyl chloronitroacetate (V) and chloronitroacetamide (VI) were calculated by the MNDO method. On the basis of the calculated data and their comparison with the data from x-ray crystallographic analysis (XCA) it was concluded that the nitro group in (II) and (III) is substituted relatively easily, that the order of the C-N bond in (V) and (VI) is close to first, that the charges in the anions alternate, and that there is no conjugation in the C-Cl bond in the.
KeywordsEthyl Chlorine Geometric Parameter Acid Derivative Halogen
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