Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Saeed, Aamer; Ashraf, Saba; White, Jonathan M.; Soria, Delia Beatriz; Franca, Carlos A.; Erben, Mauricio F.

doi:10.1016/j.saa.2015.05.068

Cited by 43 publications

(24 citation statements)

References 59 publications

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“…This assignment is in agreement with those previously reported for related substituted thioureas [39,63]. This assignment is in agreement with those previously reported for related substituted thioureas [39,63].…”

Section: Vibrational Analysissupporting

confidence: 94%

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

et al. 2015

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1-benzyl-3-furoyl-1-phenylthiourea is a thiourea derivative synthesized and characterized by means of vibrational spectroscopy (IR and Raman) multinuclear NMR ( 1 H and 13 C) and elemental analysis. The geometrical parameters of this compound obtained from XRD studies were compared with the calculated values [B3LYP/6-311++G(d,p)] showing a good agreement. As determined by XRD analysis performed previously, the title compound exhibits the U-shape conformation with the C=O and C=S double bonds in anticlinal geometry. This conformational feature is mainly dictated by the substitution degree on the thiourea core and the ability of forming and intramolecular N-H···O=C hydrogen bond. The UV-visible absorption spectra of the compound in methanol solution were recorded and analyzed using time dependent density functional theory (TD-DFT). Molecular stability was investigated by applying the natural bond (NBO) analysis. Intermolecular interactions were evaluated by means of AIM approach. The calculated HOMO and LUMO energies show that the charge transfer occurs in the molecule. The molecular electrostatic potential map was calculated by DFT method. Non-linear optical (NLO) behavior of the title compound was investigated by determining of electric dipole moment, polarizability α, and hyperpolarizability β using B3LYP/6-311++G(d,p) approximation.

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Section: Vibrational Analysissupporting

confidence: 94%

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

et al. 2015

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“…Both the co-crystal and the previously reported N -carbamothioylacetamide have the same space group of P -1 [ 30 ]. However, further literature search revealed that the crystal structure of the ring-substituted thiourea compounds are available [ 31 , 32 ]. The structure reported in this reference (CDS refcode KECHIJ01 and deposition number 1009665) [ 30 ], was the only structure which shared very close identities with the titled co-crystal, asides from the others with ring structures and thiourea moieties, whose properties have been well documented [ 31 , 32 ].…”

Section: Resultsmentioning

confidence: 99%

Supramolecular architecture in 1:1 cocrystal of N-carbamothioylacetamide and N,N′-thiocarbonyldiacetamide from the attempted synthesis of 1,3-diacetyl-2-thioxoimidazolidine-4,5-dione (a thioparabanic acid derivative)

Durosinmi

Fadare

Sanusi

et al. 2020

Heliyon

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An attempt to synthesize thioparabanic acid as precursor to other fused heterocyclic compounds, by a microwave assisted multistep one-pot reaction yielded a co-crystal of N -carbamothioylacetamide (NCTA) and N , N′ -thiocarbonyldiacetamide (NNTCA) which is being reported in this paper. The structure of N -carbamothioylacetamide and N,N′ -thiocarbonyldiacetamide from the attempted synthesis of 1,3-diacetyl-2-thioxoimidazolidine-4,5-dione, C 5 H 8 N 2 O 2 S.C 3 H 6 N 2 OS, has triclinic ( P-1 ) symmetry. It is of interest with respect to biological application. The structure displays inter- and intra-molecular hydrogen bonding through –C=O···H interactions. Similarly, –C=S···H hydrogen bonding interactions are present, providing additional intermolecular stability to the co-crystal. For application as a potential drug candidate, a density functional theory (DFT) simulation of the antioxidant activities of the co-crystal and its individual components (NCTA and NNTCA) has been performed. The computed redox potentials indicate that the study compounds show comparable antioxidant activities with ascorbic acid (AA) for a one electron transfer process. Meanwhile, for a two-electron process, AA showed significant antioxidant advantage over the titled compound.

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“…Figure depicts the experimental UV‐Vis spectra of both compounds in Dimethyl sulfoxide (DMSO) in the 230–800 nm range. The spectra are also evaluated from the calculated vertical electronic transitions energies and oscillator strengths between the initial and final states . The assigned transitions with major contributions for I and II are shown in Table and the character of the orbitals involved in the main electronic transitions for compounds I and II are shown in Figure for a better description of the electronic properties.…”

Section: Resultsmentioning

confidence: 99%

Interplay between Conformation and Crystal Packing in Aryl Propargyl Ethers: Structural and Spectroscopic Properties of 2‐(prop‐2‐yn‐1‐yloxy)acene Derivatives

et al. 2019

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The 2-(prop-2-yn-1-yloxy)naphthalene (compound I) and 1nitro-2-(prop-2-yn-1-yloxy)benzene (compound II) were prepared in excellent yields by the reaction of propargyl bromide with 2-naphthol and 2-nitrophenol, respectively. Structural and conformational properties of both compounds have been analyzed using a combined approach including single-crystal X-ray diffraction and quantum chemical calculations. Two forms are found to be stable and nearly isoenergetic conformers, depending on the mutual orientation of the C � C triple bond and the O-C single bond of the prop-2-yn-1-yloxy group. The gauche conformation is the most stable form for the vacuum isolated species, with the anti conformation higher in energy by 1.00 and 1.89 kcal/mol computed at the M06-2X/6-311 + + G(d,p) level of approximation, for I and II, respectively. The gauche form is observed in the crystal of I but the nearly planar anti conformation is adopted in the crystalline phase of compound II. The occurrence of C-H⋅⋅⋅π and C-H⋅⋅⋅O intermolecular interactions involving the acidic -C � C-H hydrogen donor and -C � C-and -OCH 2 -acceptors is discussed. Furthermore, vibrational features of the prop-2-yn-1-yloxy moiety are analyzed by infrared and Raman spectroscopy. The UV-Vis spectrum shows the presence of well-defined absorption at ca. 280 and 320 nm assigned to the π!π* transitions in the naphtyl/benzyl and prop-2-yn-1-yloxy groups, respectively.

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Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Cited by 43 publications

References 59 publications

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

Supramolecular architecture in 1:1 cocrystal of N-carbamothioylacetamide and N,N′-thiocarbonyldiacetamide from the attempted synthesis of 1,3-diacetyl-2-thioxoimidazolidine-4,5-dione (a thioparabanic acid derivative)

Interplay between Conformation and Crystal Packing in Aryl Propargyl Ethers: Structural and Spectroscopic Properties of 2‐(prop‐2‐yn‐1‐yloxy)acene Derivatives

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