Acta Chimica Sinica ›› 2002, Vol. 60 ›› Issue (2): 228-233. Previous Articles     Next Articles

Original Articles

N-苄叉基-1-氨基-萘及其类似物的构象与分子扭曲的共轭 驱动力

郭彦伸;虞忠衡;金祥林   

  1. 中国科学院化学研究所.北京(100080);分子动态与稳态结构国家重点实验室; 北京大学化学与分子工程学院.北京(100871);分子动态与稳态结构国家重点实验 室
  • 出版日期:2002-02-15 发布日期:2002-02-15

The conformation of N-(phenylmethylene)- 2-naphthaleneamine-like species and the π-driving force for distorting geometry

Guo Yanshen;Yu Zhongheng;Jin Xianglin   

  1. Inst of Chem, CAS.Beijing(100080);Beijing Univ, North-China Univ of Electr Power.Beijing(100871)
  • Online:2002-02-15 Published:2002-02-15

The crystal structures of N-{[4-(dimethylamino)phenyl] methylene}-2- benzoimidazoleamine(1), N-{[4-(dimethylamino) phenyl]methylene}-2- benzothiazoleamine (2) and N-(phenylmethylene)-2-naphthaleneamine (3) were determined. Twenty-three rotational eometries (θ=0°~-89°) of each of the molecules were optimized using AM1, RHF/STO-3G, 4-31G, 6- 311G, 6-311G and B3LYP/4-31G, 6-311G, 6-311G. The torsional angles of the preferential geometries of compound 1, 2 and 3 are close to the experimental values (1, θ=-10.69°; 2, θ=-11.99°; 3, θ=-52.88°) in the case of any optimized method. Although different optimized methods provide a specific molecule with different preferential geometries, the electron interaction always favors a twisted geometry and the nuclear repulsion is, practically, a resistance for distortion of th emolecule, which is not an artifact of a specific optimized method. The π system in the geometry with θ=0° is most destabilized no matter whether it is delocalized or not. It appears that the π system always prefers a twisted geometry.

Key words: BENZYLIDENE, NAPHTHALENE P, CONFORMATION, BENZIMIDAZOLE P, QUANTUM CHEMISTRY, CONJUGATE FUNCTIONS, CONJUGATE, CRYSTAL STRUCTURE

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