Science and Technology of Energetic Materials

Vol.65, No.6 (2004)

Research paper

Theoretical study on the effect of intramolecular amino groups on C-NO2 bond
- Amino and nitro substitutes of alkane, ethene and 1,3-butadiene -
Zhang Chaoyang, Shu Yuanjie, Huang Yigang, Zhao Xiaodong, Wang Xinfeng, and Dong Haishan


For the first time, the population of nitro group is defined as the ability to attract electrons (τ) and a criterion for measuring sensitivity of nitro compounds in this paper. The larger τ is, the less sensitivity will be. The effects of amino groups of different positions and quantity on C-NO2 bonds are studied systematically at B3LYP/6-31G (d, p) level. The results indicate that: (1) For amino and nitro substitutes of alkanes, the effects of amino groups on C-NO2 bond are inductive effects and spatial effects, and these effects will be very weak when the amino group and nitro groups are separated by more than 2 carbon atoms. (2) For amino and nitro substitutes of ethylene, amino group on No.1 position weakens C-NO2 bond, on No.2 position strengthens it: the more amino groups, the shorter C-NO2 bond, the stronger electro-negativity on carbon atom of C-NO2 bond, the longer the bond length of C=C, the more τ. That is to say, amino group is a very strong donor of electron and in the whole molecule the configuration effect is very large. (3) For amino and nitro substitutes of 1,3-butadiene, effects on C-NO2 bond occurred by amino groups are kin to orientation effect on benzene ring when hydrogen bonds are not formed by H atoms in amino groups and O atoms in nitro groups; but the effects above will be weakened if hydrogen bonds formed (the stronger hydrogen bonds, the weaker C-NO2 bond).

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