Investigations based on non-covalent interactions in 1-(4-chloromethylbenzoyl)-3-(4, 6-di-substituted pyrimidine-2-yl)thioureas: Synthesis, characterizations and quantum chemical calculations

Huang, Jie; Qiao, Lei; Zhang, Xing; Cao, Weili; Ding, Zimei; Hang, Xiaojing; Qin, Baofu; Song, Jirong

doi:10.1016/j.molstruc.2018.05.059

Cited by 13 publications

(4 citation statements)

References 41 publications

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“…This red shift is due to the formation of an intramolecular hydrogen bond between the hydrogen atom of the H-N-C = S group and the oxygen atom of the C = O group. The intense absorption bands appeared at 1651 cm −1 for both compounds correspond to the carbonyl amide (NH-C = O) stretching mode which in the same arguments with previously reported parent thiourea (RC(O)NHC(S)NHR') species occurring at region 1650-1700 cm −1 [30]. This low frequency value for 1-acyl thiourea is usually explained as due to the conjugated resonance as well as the intramolecular hydrogen bonding between the carbonyl oxygen atom and a hydrogen atom from amide moiety.…”

Section: Vibrational Analysissupporting

confidence: 88%

“…In the crystal packing as illustrated in Fig. 3, the molecules are linked by intermolecular N2-H1N2⋯S1, C2-H2⋯O3, and C4-H4A⋯O2 hydrogen bonds, forming R 2 2 (8), R 2 (30), and R 2 2 (10) graph-set motifs, respectively. These ring motifs further connect the molecules into a 2-dimensional plane and further stabilised the crystal structure.…”

Section: Structural Characteristic Of Th2mentioning

confidence: 99%

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A Dual Approach on Experimental, Theoretical Insight of Structural Elucidation, Hirshfeld Surface Analysis, Optical and Electrochemical Properties of Acyl Thiourea-Ethynyl Hybrid Derivatives

et al. 2022

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Hybrid moieties of ethynylated-thiourea, Th1 and Th2 have been synthesised via the addition reaction between ethynyl derivatives and 4-tert-butylbenzoyl isothiocyanate in acetone, and were characterised by selected spectroscopic methods (i.e., 1 H and 13 C NMR, UV-visible, FT-IR) and elemental analysis. Thermogravimetric analysis indicated that Th1 and Th2 were relatively stable up to ca. 210 °C. Single-crystal X-ray diffraction was used to identify the crystal structure of Th2 in which the centre of 1-acyl thiourea moiety (-C(O)NHC(S)NH) exhibits S conformation. The Hirshfeld surface analysis has allowed visualizing the crystal packing, which is characterised by the prolonged intermolecular N-H⋯O = C and N-H⋯S = C hydrogen-bonding interactions within Th2 molecule. Electrochemical data of both compounds correspondingly exhibit irreversible redox potential processes. Besides, frontier molecular orbitals and Natural Bond Orbital population analysis were computed at the B3LYP/6-31G (d, p) level of approximation, suggesting strong delocalization of the electronic density through a conjugated π-system involving the ethynyl-phenyl and thiourea groups.

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Section: Vibrational Analysissupporting

confidence: 88%

Section: Structural Characteristic Of Th2mentioning

confidence: 99%

A Dual Approach on Experimental, Theoretical Insight of Structural Elucidation, Hirshfeld Surface Analysis, Optical and Electrochemical Properties of Acyl Thiourea-Ethynyl Hybrid Derivatives

et al. 2022

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“…Molecular interactions are involved in the structure stability of a given material. Such interactions, act to weak intramolecular intermolecular interactions that in turn are able to be detected by reduced density gradient (RDG) analysis, this analysis relies on the analysis of non-covalent interactions (NCI) that exist in the system [26]. The NCI-RDG analysis is plotted in Fig.…”

Section: Density Gradient (Nci-rdg) Analysismentioning

confidence: 99%

Investigations on Growth, Characterization, NCI-RDG, AIM, Molecular Docking and In-Silico ADME Properties of 1,2-Benzene Dicarboxylic Acid Anhydride

G.,

M.,

et al. 2024

Orbital: Electron. J. Chem.

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Superior single crystal of 1,2-benzene dicarboxylic acid anhydride additionally called Phthalic anhydride (PAN) was developed via solution growth at low temperatures. Single crystal X-ray diffraction investigation revealed the crystal system and unit cell characteristics. The phase stability and crystalline nature were uncovered by powder X-ray diffraction analysis. FT-IR examination was done for the titular material so as to survey the various functional groups. With the use of the VEDA program's relevant resources, vibrational assignments have been made on the concept of Potential Energy Distribution (PED). Density Functional Theory (DFT) was employed to smooth out the molecular structure of PAN and was additionally utilized to consider FT-IR spectrum at molecular level. Non covalent interactions reduced density gradient (NCI-RDG) analysis has been used for the prediction of the weak interaction in the actual space in terms of the electron density along with its derivatives for PAN. Atoms in Molecules (AIM) analysis was carried for out for PAN. The docking research of the small molecule (PAN) with target protein confirmed that this is a great molecule which docks nicely with numerous targets associated with Hypoxia Inducible Factor 1-α. The absorption, distribution, metabolism, excretion (ADME) characteristics have been calculated with the assist of online server preADMET.

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“…Besides, the type and intensity of noncovalent interaction (NCI) can be visually analyzed by electron density and reduced density gradient (RDG) function . Apart from the hydrogen bonding interactions, the NCI analysis reveals the presence of other weak NCIs such as CH … π lone pair, CH … π contacts, Van der Waals interactions, and steric hindrance in the solid state structure of acyl thiourea derivatives . Thence, the NCIs in the crystal of compound play an important role in stabilizing molecules with a special mode of action, and it is worthwhile to our attention …”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure, hydrogen bonding interactions analysis of novel acyl thiourea derivative

Zhang

Du²,

Song

et al. 2019

J of Physical Organic Chem

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The N-(p-methoxybenzoyl)-N 0 -(2,4-dinitrophenyl amino)thiourea has been synthesized and characterized by FT-IR, 1 H NMR, and elemental analyses techniques. Also, its molecular structure was determined by single-crystal Xray diffraction. It revealed that the title compound crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell, space groupPna2 (1) with a = 18.857(5) Å, b = 8.148(2) Å, c = 22.443(6) Å, β = 90.00 , C 15 H 13 N 5 O 6 S, M r = 391.36, V = 3448.2(15) Å 3 , Z = 8, D c = 1.508 gÁcm −1 , F(000) = 1616, μ = 0.233 mm −1 , S = 1.06, the final R = 0.0626, and wR (I > 2(I)) = 0.1392.

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Investigations based on non-covalent interactions in 1-(4-chloromethylbenzoyl)-3-(4, 6-di-substituted pyrimidine-2-yl)thioureas: Synthesis, characterizations and quantum chemical calculations

Cited by 13 publications

References 41 publications

A Dual Approach on Experimental, Theoretical Insight of Structural Elucidation, Hirshfeld Surface Analysis, Optical and Electrochemical Properties of Acyl Thiourea-Ethynyl Hybrid Derivatives

A Dual Approach on Experimental, Theoretical Insight of Structural Elucidation, Hirshfeld Surface Analysis, Optical and Electrochemical Properties of Acyl Thiourea-Ethynyl Hybrid Derivatives

Investigations on Growth, Characterization, NCI-RDG, AIM, Molecular Docking and In-Silico ADME Properties of 1,2-Benzene Dicarboxylic Acid Anhydride

Synthesis, crystal structure, hydrogen bonding interactions analysis of novel acyl thiourea derivative

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