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Citation: Xiao He-Ming, Tang Ze-Hua, Chen Li, Deng Ya. The Relations Between Properties and Electronic Structure of Cyclourea Nitroamine Compounds II. Hydrolytic Stability[J]. Acta Physico-Chimica Sinica, ;1990, 6(04): 499-503. doi: 10.3866/PKU.WHXB19900421 shu

The Relations Between Properties and Electronic Structure of Cyclourea Nitroamine Compounds II. Hydrolytic Stability

1.
East China Institute of Technology, Nanjing

Received Date: 8 December 1988
Available Online: 15 August 1990

The eleven title compounds are classified into three series according to their molecular structure having mono-, bi- and tri-condensed ring system, respectively. For each series the hydrolytic stabilities decrease with the increase of the calculated CNDO/2 net positive charge on C atom of carbonyl group. This relation supports the kinetic hydrolysis mechanism, in which the hydrolysis reaction is initiated by the nucleophylic attack on the C atom of the carbonyl group. It can be applied to predict the relative stsbility of some cyclourea nitroamines by means of similar theoretically calculated parameters. For bi- and tri-condensed ring compounds, which have V- and U-type optimized configurations respecively, the steric hindrance due to the C=O group covering large —CH_2C(NO_2)_3 group plays an important role also, especially for the V-type bi-condensed ring compounds.
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