Acta Phys. -Chim. Sin. ›› 2017, Vol. 33 ›› Issue (2): 356-363.doi: 10.3866/PKU.WHXB201610191

• ARTICLE • Previous Articles     Next Articles

Crystal Structure, Thermal Decomposition and Interaction with CT-DNA of Three 2-Hydroxy-1-naphthaldehyde Acyl Hydrazones

Shun-Sheng ZHAO,Lan-Lan LI,Xiang-Rong LIU*(),Zuo-Cheng DING,Zai-Wen YANG   

  • Received:2016-09-05 Published:2017-01-12
  • Contact: Xiang-Rong LIU
  • Supported by:
    the National Natural Science Foundation of China(21103135,21073139,21301139);Natural Science Basic Research Plan in Shaanxi Province, China(2016JM2011);Scientific Research Program Funded by Shaanxi Provincial Education Commission, China(15JK1492)


Three acyl hydrazones N'-((2-hydroxynaphthalen-1-yl)methylene)-2-phenylacetohydrazide (1), N'-((2-hydroxynaphthalen-1-yl) methylene)-2-(4-hydroxyphenyl)acetohydrazide hydrate (2), and N'-((2-hydroxynaphthalen-1-yl) methylene)-2-(2-methoxyphenyl) acetohydrazide hydrate (3) were synthesized and then characterized by elemental analysis and single-crystal X-ray diffraction. The crystallographic data indicated that both compounds 2 and 3 crystallized in the monoclinic crystal lattice, space group C2/c, while compound 1 crystallized in the orthorhombic space group Pbca. The thermal decomposition processes of the three hydrazones were studied by thermogravimetry. The thermal decomposition temperatures of compounds 1, 2, and 3 were 318.23, 319.04, and 323.01℃, respectively. Meanwhile, the apparent activation energies for thermal decomposition for compounds 1, 2, and 3 were 115.90, 145.18, and 129.38 kJ·mol-1, respectively, calculated according to the Kissinger and Ozawa equations. The interactions of compounds 1-3 with calf thymus (CT)-DNA were evaluated by microcalorimetry. The results indicated these interactions were homogenous endothermic processes with non-identical interaction time (1.00-50.0 min) and interaction enthalpies (0.47-15.50 kJ·mol-1). The interaction enthalpies of compounds 1 and 2 were higher than those of their precursors, while the interaction enthalpy of compound 3 was lower than that of its precursor.

Key words: Acyl hydrazone, Crystal structure, Thermogravimetry, Microcalorimetry, DNA binding