Supramolecular self-assembly of new thiourea derivatives directed by intermolecular hydrogen bonds and weak interactions: crystal structures and Hirshfeld surface analysis

Gümüş, İlkay; Solmaz, Ummuhan; Binzet, Gün; Keskin, Ebru; Arslan, Birdal; Arslan, Hakan

doi:10.1007/s11164-018-3596-5

Cited by 28 publications

(9 citation statements)

References 68 publications

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“…[ 30,31 ] The Hirshfeld surface analysis and two‐dimensional fingerprint plots of the synthesized compounds were obtained by CrystalExplorer 3.1. [ 20,32,33 ]…”

Section: Methodsmentioning

confidence: 99%

Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies

Wang

Zhang

Fan

et al. 2020

J of Physical Organic Chem

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Two novel thiosemicarbazone derivatives (E)‐N‐(3,5‐dimethylphenyl)‐2‐(3‐methylbenzylidene)thiosemicar‐bazone (1) and (E)‐N‐(3,5‐dimethylphenyl)‐2‐(3‐fluorobenzylidene)thiosemicarbazone (2) had been synthesized and characterized by FT‐IR, nuclear magnetic resonance, and elemental analysis. Single crystal X‐ray diffraction analysis showed that compound 1 belongs to triclinic system in P‐1 space group and compound 2 belongs to monoclinic system in C2/c space group. It could be seen from the determined crystal structure that the central skeleton NNHC(S)NH of both thiosemicarbazone compounds have good planarity. Density functional theory (DFT) calculations were done using B3LYP/6‐31+G(d, p) basis set and the calculated results are in good agreement with the experimental data. In addition, the UV‐visible absorption spectrum was estimated based on TD‐DFT quantum chemistry calculations. Likewise, the simulated absorption spectrum is very consistent with the experimental data. Combining Hirshfeld surface analysis and molecular structure, it was found that the intermolecular hydrogen bond NH···SC constitutes central symmetric dimer . Through quantum chemical calculation, we investigated the reduced density gradient function and the independent gradient model, which provided a deeper insight into the intermolecular and intramolecular interaction force of the compounds. The frontier molecular orbital analysis and molecular electrostatic potential were also discussed by theoretical calculations.

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“…[ 30,31 ] The Hirshfeld surface analysis and two‐dimensional fingerprint plots of the synthesized compounds were obtained by CrystalExplorer 3.1. [ 20,32,33 ]…”

Section: Methodsmentioning

confidence: 99%

Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies

Wang

Zhang

Fan

et al. 2020

J of Physical Organic Chem

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“…[ 27 ] The Hirshfeld surface analysis and 2D fingerprint plots of the synthetic compound were obtained by CrystalExplorer 3.1. [ 28,29 ] The crystal structure of the synthetic compound was obtained through the MERCURY program, [ 30 ] the structure stacking diagram was obtained using the Diamond software program. [ 31 ] Moreover, additional geometrical data were calculated using the PLATON program.…”

Section: Methodsmentioning

confidence: 99%

Study on the synthesis and theoretical calculation of a chlorine‐substituted thiosemicarbazone derivative

Wei

Wang

Deng

et al. 2021

J of Physical Organic Chem

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In this paper, the compound (E)-N-(3,5-dimethylphenyl)-2-(3-chlorobenzylidene)thiosemicarb-azone was synthesized and characterized by elemental analysis, Fourier transform infrared (FT-IR), 1 H nuclear magnetic resonance (NMR), 13 C NMR. The crystal structure was determined by single-crystal X-ray diffraction tool, indicating that the compound belongs to the orthorhombic crystal system of the Fdd2 space group, where

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“…The medium intensity IR absorption bands observed 834 and 854 cm −1 for the title compounds are assigned to the ν(C=S) mode of the thiourea derivatives. The formation of C=S…Hintermolecular hydrogen bonds seem to strongly affect the frequency of the (C=S) mode [20,21] The 1 H-NMR spectrum of the title compounds indicate that the synthesized structures are aroyl thioureas derivatives. The signals that appeared at δH 12.70, 11.69 ppm and 12.47 and 12.04 ppm are characteristic of the N-H protons of the thiourea moiety for the title compounds 1 and 2, respectively [22].…”

Section: Spectroscopic Studiesmentioning

confidence: 99%

“…The medium intensity IR absorption bands observed 834 and 854 cm −1 for the title compounds are assigned to the ν(C=S) mode of the thiourea derivatives. The formation of C=S...H-intermolecular hydrogen bonds seem to strongly affect the frequency of the (C=S) mode [20,21].…”

Section: Spectroscopic Studiesmentioning

confidence: 99%

Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-aroyl-N′-(4′-cyanophenyl)thioureas

Aydın

Arslan

2022

Molbank

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Herein, two title compounds, N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2) were synthesized in a high yield, via different applications of aroyl isocyanate and 4-aminobenzonitrile. The structure of the prepared compounds was characterized by elemental analysis and FT-IR, 1H, and 13C-NMR spectroscopic methods. The crystal structure of the title compound 1 was determined by an X-ray single-crystal technique and an intramolecular C=O…H-N hydrogen bond and intermolecular C=S…H-N and C=S…H-C hydrogen interactions, which were observed for the crystal structure. The molecular electrostatic potential (MEP) and the Mulliken atomic charges of title compounds 1 and 2 were theoretically calculated and interpreted. Cyclic voltammetric (CV) experiments for the compounds were performed with the glassy carbon electrode. The reduction in potential values of the different functional groups such as nitro and cyano in title compounds were investigated using CV curves.

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Supramolecular self-assembly of new thiourea derivatives directed by intermolecular hydrogen bonds and weak interactions: crystal structures and Hirshfeld surface analysis

Cited by 28 publications

References 68 publications

Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies

Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies

Study on the synthesis and theoretical calculation of a chlorine‐substituted thiosemicarbazone derivative

Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-aroyl-N′-(4′-cyanophenyl)thioureas

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