Synthesis, Crystal Structure and Non-covalent Interactions Analysis of Novel N-Substituted Thiosemicarbazone

被引:12
作者
Zhang Xing [1 ]
Huang Jie [1 ]
Zhang Yu [1 ]
Qi Fan [1 ]
Wang Sifan [1 ]
Song Jirong [2 ]
机构
[1] Northwest Univ, Sch Chem Engn, Shaanxi Key Lab Phys Inorgan Chem, Xian 710069, Shaanxi, Peoples R China
[2] Minist Sci & Technol, Palace Museum, Beijing 100009, Peoples R China
关键词
Novel N-substituted thiosemicarbazone; Non-covalent interaction; Reduced desity gradient(RDG) function; Hirshfeld surface analysis; ASSISTED PARALLEL SYNTHESIS; HIRSHFELD SURFACE-ANALYSES; INTERMOLECULAR INTERACTIONS; BIOLOGICAL EVALUATION; ANTIMICROBIAL ACTIVITY; QUANTITATIVE-ANALYSIS; PI INTERACTIONS; DERIVATIVES; THIOUREAS; DOCKING;
D O I
10.1007/s40242-019-8354-8
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(E)-1-(4-Fluorobenzylidene)-4-(4-ethylphenyl)thiosemicarbazone was synthesized via the reaction of 4-(4-ethylphenyl)thiosemicarbazide and 4-fluorobenzaldehyde. The title compound was characterized by FTIR, H-1 and C-13 NMR, mass spectrometry and elemental analysis techniques. Structural property of the title compound was displayed by the X-ray single crystal diffraction. The title compound crystallized in triclinic space group P (1) over bar with a=0.6494(4) nm, b=0.7971(5) nm, c=1.5492(10) nm, alpha=83.690(11)degrees, beta-84.185(10)degrees, gamma=84.348(11)degrees, molecular formula C16H16FN3S, M-r=301.39, V=0.7868(9) nm(3), Z=2, D-c=1.272 g/cm(3), F(000)=316, mu=0.213 mm(-1), S=1.02, R=0.0513, and omega R[I>2 sigma(I)]=0.1662. The intermolecular interactions in the crystal structure were explained using the Hirshfeld surface and their associated two-dimensional fingerprint plots. The title compound showed C-H center dot center dot center dot S(1-x, -y, -z) and N-H center dot center dot center dot S(1-x, -y, -z) intermolecular interactions, and formed the supramolecular self-assemblies through R-2(2)(12) and R-2(2)(8) ring motifs. Shape index and curvedness were performed to further understand some unique weak interactions, for instance, the weak pi center dot center dot center dot pi stacking contacts in molecular structure with different characteristic regions. Besides, the reduced density gradient(RDG) function provided a real-space function for discussing non-covalent interactions within molecule, such as hydrogen bonds, weak van der Waals interactions and attractive or repulsive effects.
引用
收藏
页码:471 / 477
页数:7
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共 50 条
  • [1] Amir A, 2007, EUR J MED CHEM, V35, P1300
  • [2] Amir A J, 2004, J BIOORG MED CHEM LE, V12, P4679, DOI [10.1016/j.bmc.2004.06.036, DOI 10.1016/J.BMC.2004.06.036]
  • [3] Andreas J K, 2011, EUR J MED CHEM, V46, P1656, DOI [10.1016/J.EJMECH.2011.02.014, DOI 10.1016/J.EJMECH.2011.02.014]
  • [4] Synthesis, spectral and biological evaluation of some new thiazolidinones and thiazoles based on t-3-alkyl-r-2,c-6-diarylpiperidin-4-ones
    Aridoss, G.
    Amirthaganesan, S.
    Kim, M. S.
    Kim, J. T.
    Jeong, Yeon Tae
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (10) : 4199 - 4210
  • [5] Synthesis, cytotoxicity and antimicrobial activity of thiourea derivatives incorporating 3-(trifluoromethyl)phenyl moiety
    Bielenica, Anna
    Stefanska, Joanna
    Stepien, Karolina
    Napiorkowska, Agnieszka
    Augustynowicz-Kopec, Ewa
    Sanna, Giuseppina
    Madeddu, Silvia
    Boi, Stefano
    Giliberti, Gabriele
    Wrzosek, Malgorzata
    Struga, Marta
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 101 : 111 - 125
  • [6] New isoxazole(3,5)substituted thiosemicarbazone: Synthesis, crystal structure and spectroscopic studies of the binding mode to protein and calf thymus DNA
    Bomfim Filho, Lucius F. O.
    Barbosa, Rafaela S.
    Burgos C, Ana E.
    Rodrigues, Bernardo L.
    Teixeira, Leticia R.
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2017, 1150 : 44 - 54
  • [7] Molecular and crystal structure of quinoline-2-aldehyde thiosemicarbazone
    Bourosh, P. N.
    Revenko, M. D.
    Gdaniec, M.
    Stratulat, E. F.
    Simonov, Yu. A.
    [J]. JOURNAL OF STRUCTURAL CHEMISTRY, 2009, 50 (03) : 510 - 513
  • [8] Erdal O, 1995, J TERMOCHIM ACTA, V254, P371, DOI [10.1016/0040-6031(94)02107-Y, DOI 10.1016/0040-6031(94)02107-Y]
  • [9] Halogen bonding in solution
    Erdelyi, Mate
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3547 - 3557
  • [10] Frisch M.J., 2016, GAUSSIAN 16