Crystals

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16 pages, 4991 KiB

Open AccessArticle

Cytotoxicity and Apoptosis-Induction in MCF-7 Cells for New Pd(II) Complex Based on s-Triazine Ligand: Synthesis, Single Crystal X-ray Diffraction Analysis and Structural Investigations

by Abdulmajeed Abdullah Alayyaf, Assem Barakat, Abdullah Mohammed Al-Majid, M. Ali, Sammer Yousuf, Matti Haukka, Ayman El-Faham, Saied M. Soliman and Mohamed S. Nafie

Crystals 2023, 13(10), 1472; https://doi.org/10.3390/cryst13101472 - 10 Oct 2023

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Abstract

The synthesis and X-ray structure analysis of the new [PdLCl₂]*0.5 CH₂Cl₂ complex where L is hydrazono-s-triazine di-morpholine derivative, were presented. In the neutral inner sphere of this complex, the organic ligand L is acting [...] Read more.

The synthesis and X-ray structure analysis of the new [PdLCl₂]*0.5 CH₂Cl₂ complex where L is hydrazono-s-triazine di-morpholine derivative, were presented. In the neutral inner sphere of this complex, the organic ligand L is acting as a NN-bidentate chelate via the pyridine and hydrazone N-atoms. The coordination configuration of the Pd(II) is completed by two chloride ions at cis-positions. The tetra-coordinated Pd(II) showed a distorted square planar geometry. The outer sphere comprised half methylene chloride molecule per [PdLCl₂] as crystal solvent. The crystal stability is dominated by a number of weak C-H…N, C-H…Cl, and C-H…O non-covalent interactions. Based on Hirshfeld analysis, the H…H, N…H, H…Cl, O…H, Pd…C, and Cl…C intermolecular interactions contributed by 45.2, 9.3, 21.5, 5.8, 2.3, and 3.4%, respectively. DFT studies revealed closed shell characters for the Pd-N and Pd-Cl coordinate bonds. The net charge of Pd is also predicted to be 0.311 e and the amount of electron density transferred from the ligand groups is 1.689 e. The Pd(II) complex exhibited potent cytotoxic activity against MCF-7, HepG2, and A549 cells with IC₅₀ values of 1.18, 4.74, and 5.22 μg/mL, compared to cisplatin with IC₅₀ values of 4.1, 9.7, and 12.3 μg/mL, respectively. Additionally, it exhibited poor cytotoxicity against WISH cells with much higher IC₅₀ values (IC₅₀ = 37.2 μg/mL). Investigating apoptosis-induction, the Pd(II) complex induced apoptotic cell death by an 11-fold change in MCF-7 cells arresting the cell phase at the G0–G1 phase. Accordingly, Pd(II) complex can be developed as a promising anti-breast cancer agent. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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13 pages, 2990 KiB

Open AccessArticle

Schiff Base Derivatives in Zinc(II) and Cadmium(II) Complexation with the closo-Dodecaborate Anion

by Svetlana E. Nikiforova, Nadezhda A. Khan, Alexey S. Kubasov, Yurii V. Koshchienko, Anatolii S. Burlov, Lyudmila N. Divaeva, Lyudmila V. Goeva, Varvara V. Avdeeva, Elena A. Malinina and Nikolay T. Kuznetsov

Crystals 2023, 13(10), 1449; https://doi.org/10.3390/cryst13101449 - 29 Sep 2023

Cited by 1 | Viewed by 565

Abstract

A series of Schiff base derivatives, namely N-(4-methoxyphenyl)-1-(1-methylbenzimidazol-2-yl)methanimine (L¹), 4-methoxy-N-[(1-methylbenzimidazol-2-yl)methyl]aniline (L²), and 2-[(E)-(1-propylbenzimidazol-2-yl)iminomethyl]phenol (L³), were synthesized. These compounds feature different linker groups, including –CH=N–, –CH₂–NH–, and –N=CH–, respectively. During the [...] Read more.

A series of Schiff base derivatives, namely N-(4-methoxyphenyl)-1-(1-methylbenzimidazol-2-yl)methanimine (L¹), 4-methoxy-N-[(1-methylbenzimidazol-2-yl)methyl]aniline (L²), and 2-[(E)-(1-propylbenzimidazol-2-yl)iminomethyl]phenol (L³), were synthesized. These compounds feature different linker groups, including –CH=N–, –CH₂–NH–, and –N=CH–, respectively. During the process of zinc(II) and cadmium(II) complexation in the presence of the closo-dodecaborate [B₁₂H₁₂]^2– anion, it was observed that ligand L³ underwent degradation. Consequently, two compounds were isolated, [Zn(Bz-NH₂)₂(CH₃COO)₂] and (HBz-NH₂)₂[B₁₂H₁₂]∙2CH₃CN, both containing 1-propyl-2-aminobenzimidazole (Bz-NH₂), which is a degraded fragment of the ligand. Several new zinc(II) and cadmium(II) coordination compounds were synthesized and characterized using various physicochemical analysis methods, including elemental analysis, IR, and UV spectroscopy. Additionally, X-ray diffraction and Hirshfeld surface analysis were performed for compounds [Cd(L²)₂(CH₃CN)(H₂O)][B₁₂H₁₂], [Zn(Bz-NH₂)₂(CH₃COO)₂], and (HBz-NH₂)₂[B₁₂H₁₂]∙2CH₃CN, as well as for ligand L². Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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13 pages, 3739 KiB

Open AccessArticle

Rapid and Selective Sensing of 2,4,6-Trinitrophenol via a Nano-Plate Zn(II)-Based MOF Synthesized by Ultrasound Irradiation

by Xiao-Wei Yan, Azar Hakimifar, Fahime Bigdeli, Younes Hanifehpour, Su-Juan Wang, Kuan-Guan Liu, Ali Morsali and Sang Woo Joo

Crystals 2023, 13(9), 1344; https://doi.org/10.3390/cryst13091344 - 03 Sep 2023

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Abstract

Using the sonochemical method, nano-plates of a 3D Zn(II) metal−organic framework (MOF) were synthesized and characterized using FT-IR spectroscopy and PXRD. The effect of various irradiation durations and concentrations of reagents was investigated to obtain uniform morphologies. Increasing the irradiation time along with [...] Read more.

Using the sonochemical method, nano-plates of a 3D Zn(II) metal−organic framework (MOF) were synthesized and characterized using FT-IR spectroscopy and PXRD. The effect of various irradiation durations and concentrations of reagents was investigated to obtain uniform morphologies. Increasing the irradiation time along with decreasing the reagent concentration led to the production the particles with a uniform nano-plate morphology. Also, the sensing potential of these nano-plates to detect nitroaromatic analytes such as nitrophenol, 2,4-dinitrophenol, and TNP was explored. The nano Zn MOF was highly selective and sensitive in the detection of nitroaromatic derivatives. The quenching percentages of fluorescence emissions for a 2ppb concentration of nitrophenol, 2,4-dinitrophenol, and TNP were 11%, 42%, and 89%, respectively. According to the results, the MOF has the strongest detection limit for TNP. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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13 pages, 4797 KiB

Open AccessArticle

Nanoarchitectonics and Molecular Docking of 4-(Dimethylamino)Pyridin-1-Ium 2-3 Methyl-4-Oxo-Pyri-Do[1,2-a]Pyrimidine-3-Carboxylate

by Sanae Lahmidi, El Hassane Anouar, Walid Ettahiri, Mohamed El Hafi, Fatima Lazrak, Mohammed M. Alanazi, Ashwag S. Alanazi, Mohamed Hefnawy, El Mokhtar Essassi and Joel T. Mague

Crystals 2023, 13(9), 1333; https://doi.org/10.3390/cryst13091333 - 31 Aug 2023

Cited by 2 | Viewed by 768

Abstract

A retro-Claisen reaction of 1-(4-oxo-4H-pyrido [1,2-a]pyrimidin-3-yl)butane-1,3-dione, 3, in the presence of potassium hydroxide and 4-dimethylamino-pyridine has been carried out, leading to 4-(dimethylamino)pyridin-1-ium 2-methyl-4-oxo-pyrido [1,2-a]pyrimidine-3-carboxylate 5. A plausible mechanism explaining the formation of the title compound has been [...] Read more.

A retro-Claisen reaction of 1-(4-oxo-4H-pyrido [1,2-a]pyrimidin-3-yl)butane-1,3-dione, 3, in the presence of potassium hydroxide and 4-dimethylamino-pyridine has been carried out, leading to 4-(dimethylamino)pyridin-1-ium 2-methyl-4-oxo-pyrido [1,2-a]pyrimidine-3-carboxylate 5. A plausible mechanism explaining the formation of the title compound has been proposed. A single-crystal X-ray diffraction analysis confirms the crystal structure of the isolated organic salt (5). In the crystal, the title compound adopts a layered structure where there are stacks of cations and anions formed by slipped π-stacking interactions. These stacks are linked by regions consisting of water molecules that are hydrogen-bonded together. DFT and Hirshfeld surface analysis supported the experimental results of the molecular geometry and the intercontacts between different units in the crystal. The druglikeness, ADMET properties, and predicted targets were investigated, and the observed results suggest that 5 may act as a carbonic anhydrase I inhibitor. The assumption is confirmed by docking 5 into the active binding site of carbonic anhydrase, which shows it to have good binding affinities and to form stable complexes with the active residues of carbonic anhydrase I. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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16 pages, 7082 KiB

Open AccessArticle

Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-b]indole and Its Precursor

by Ahmed T. A. Boraei, Elsayed H. Eltamany, Matti Haukka, Saied M. Soliman, Assem Barakat and Manar Sopaih

Crystals 2023, 13(7), 1036; https://doi.org/10.3390/cryst13071036 - 29 Jun 2023

Cited by 1 | Viewed by 886

Abstract

The hit compound 1,2,4-triazolo[4’,3’:2,3]pyridazino[4,5-b]indole 3 was synthesized from the reflux of 4-amino-5-indolyl-1,2,4-triazole-3-thione 1 with 4′-bromoacetophenone 2 in methanol catalyzed by concentrated HCl and the desired final molecule was obtained by recrystallization from methanol. The suggested structures of compounds 1 and 3 [...] Read more.

The hit compound 1,2,4-triazolo[4’,3’:2,3]pyridazino[4,5-b]indole 3 was synthesized from the reflux of 4-amino-5-indolyl-1,2,4-triazole-3-thione 1 with 4′-bromoacetophenone 2 in methanol catalyzed by concentrated HCl and the desired final molecule was obtained by recrystallization from methanol. The suggested structures of compounds 1 and 3 based on the spectral characterizations were confirmed by X-ray single crystal diffraction analysis. Compound 3 crystallized in the triclinic crystal system and P-1 space group with a = 5.9308(2) Å, b = 10.9695(3) Å, c = 14.7966(4) Å, α = 100.5010(10)°, β = 98.6180(10)°, and γ = 103.8180(10)°. On the other hand, the crystal system of 1 is monoclinic, where a = 6.23510(10) Å, b = 26.0156(4) Å, c = 12.4864(2) Å, β = 93.243(2)° and the space group is P2₁. The triazole and indole rings are found twisted from each other in both compounds. The twist angle is higher in 3 (12.65°) than 1 (4.94–7.22°). In the case of the former, the H…H (39.6%), H…C (22.0%), N…H (12.8%) and Br…H (13.2%) contacts are the most dominant while the C…C, C…H, Br…H, N…H and S…S contacts have the characteristics of strong interactions. In the latter, the C…H, N…H, S…H, S…S, and C…C contacts are the most important. In this case, the percentages of the H…H, C…H, N…H and S…H contacts are in the range of 34.9–37.4, 20.5–24.0, 12.2–13.6, 14.0–15.8, respectively. In both systems, the shape index and curvedness of surfaces confirmed the presence of π–π stacking interactions. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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13 pages, 3122 KiB

Open AccessArticle

Stereoselective Synthesis of New 4-Aryl-5-indolyl-1,2,4-triazole S- and N-β-Galactosides: Characterizations, X-ray Crystal Structure and Hirshfeld Surface Analysis

by Mezna Saleh Altowyan, Matti Haukka, Saied M. Soliman, Assem Barakat, Ahmed T. A. Boraei and Ahmed Aboelmagd

Crystals 2023, 13(5), 797; https://doi.org/10.3390/cryst13050797 - 10 May 2023

Cited by 3 | Viewed by 1284

Abstract

5-(1H-Indol-2-yl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione 1a and 4-(4-chlorophenyl)-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1b were galactosylated in the presence of NaHCO₃ in ethanol to produce S-galactosides 3,4, whereas, in the presence of K₂CO₃ in acetone they produced a [...] Read more.

5-(1H-Indol-2-yl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione 1a and 4-(4-chlorophenyl)-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1b were galactosylated in the presence of NaHCO₃ in ethanol to produce S-galactosides 3,4, whereas, in the presence of K₂CO₃ in acetone they produced a mixture of S- and N-galactosides 3-6 with a higher yield of S-galactosides over the respective N-galactosides. Improvement in the yields of N-galactosides was produced by thermal migration of the galactosyl moiety from sulfur to nitrogen using fusion. β-Stereoselectivity of galactosylation was determined using the coupling constant value ³J_1,2, which exceeded 9.0 Hz in all prepared galactosides. The precursors 1a and 1b alkylated with 3-bromopropan-1-ol 7 in K₂CO₃ and acetone produced the S-alkylated products 8 and 9, respectively. Structural determinations of new compounds 5 and 9 are presented. The phenyl and indole moieties were found to be twisted from the triazole ring mean in both compounds. For compound 5, the twist angles were 66.24° and 18.86°, respectively, while the corresponding values for 9 were in the ranges of 73.15–77.29° and 13.96–20.70°, respectively. Hence, the crystal system of 9 is triclinic while the space group is P-1. Detailed analysis of the intermolecular interactions in the crystal structure of 5 is presented using Hirshfeld calculations. The O…H, N…H, C…H, and S…H contacts appeared as red spots in the d_norm Hirshfeld surface indicating short distance intermolecular interactions. Their percentages were estimated based on the decomposition of the fingerprint plot to be 25.6, 2.4, 14.0, and 6.3%, respectively. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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13 pages, 3162 KiB

Open AccessArticle

Fe₂O₃-Ag₂O/TiO₂ Nanocatalyst-Assisted LC-MS/MS-Based Detoxification of Pesticide Residues in Daphnia magna and Algae Mediums

by Faheem Ahmed, Tentu Nageswara Rao, Nishat Arshi, Y. Prashanthi, Shalendra Kumar and Adil Alshoaibi

Crystals 2023, 13(4), 644; https://doi.org/10.3390/cryst13040644 - 09 Apr 2023

Viewed by 1423

Abstract

In this work, a simple sensitive validated liquid chromatography mass spectroscopy (LC-MS/MS) analytical method was developed for the determination of Spirodiclofen residues in different aquatic toxic media. The toxic media were those that provide nutrients and help with the growth of different aquatic [...] Read more.

In this work, a simple sensitive validated liquid chromatography mass spectroscopy (LC-MS/MS) analytical method was developed for the determination of Spirodiclofen residues in different aquatic toxic media. The toxic media were those that provide nutrients and help with the growth of different aquatic organisms for their survival and multiplication. The different media were the M4 medium for Daphnia magna and The Organization for Economic Cooperation and Development (OECD TG 201) medium for alga. Fe₂O₃-Ag₂O/TiO₂ nanocomposites were prepared by using a precipitation method, which was used as a photo-catalyst for the removal of Spirodiclofen pesticide from aquatic media. The experiment was performed under direct sunlight at a single fortification level (1.0 µg/mL) in M4 and OECD TG 201 media. The optimum catalyst concentration for the complete degradation was found to be 10 mg/L under sunlight. Spirodiclofen residues in water were determined by LC-MS/MS, and the rate constant DT50 (half-life) values were calculated from the obtained data. The results showed that with Fe₂O₃-Ag₂O/TiO₂ nanocatalyst, the DT50 (half-life) value was found to be approximately 8 h. These results revealed that iron-oxide- and silver-oxide-incorporated TiO₂ nanocomposites were excellent photocatalysts when compared with TiO₂, Fe₂O₃-TiO₂, and Ag₂O-TiO₂ for the decontamination of pesticide residues in aquatic media samples. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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16 pages, 4440 KiB

Open AccessArticle

Potential Applications of Chitosan-Coated Zinc Oxide Nanoparticles for Degrading Pesticide Residues in Environmental Soils

by Wafa Mahmoud Daqa, Adil Alshoaibi, Faheem Ahmed and Tentu Nageswara Rao

Crystals 2023, 13(3), 391; https://doi.org/10.3390/cryst13030391 - 24 Feb 2023

Cited by 2 | Viewed by 1951

Abstract

The precipitation process was applied to synthesize chitosan-coated zinc oxide nanoparticles (chitosan-ZnO NPs). Then, various characterization tools were used such as XDR, SEM, TEM, FTIR, and EDX. The use of these 50 nm chitosan-ZnO NPs in soil decontamination of thifluzamide and difenoconazole pesticide [...] Read more.

The precipitation process was applied to synthesize chitosan-coated zinc oxide nanoparticles (chitosan-ZnO NPs). Then, various characterization tools were used such as XDR, SEM, TEM, FTIR, and EDX. The use of these 50 nm chitosan-ZnO NPs in soil decontamination of thifluzamide and difenoconazole pesticide residues is being investigated. In two distinct soils, the effect of catalytic decontamination on pesticide residues was examined (sandy loam and sandy clay soils). The studies required two sets of pesticide concentrations. One set of samples was added to the chitosan-ZnO NPs catalyst, and the other set was studied without the addition of a catalyst. Photocatalytic studies were conducted under the sunlight in July. The soil samples were hand-spread in a glass dish to a height of 5 mm and sprayed with an aqueous solution of pesticide. From 8 a.m. to 5 p.m., these samples were exposed to sunlight in October 2021. We found that the best concentration of catalyst was 0.05%. The acquired samples were quantified using validated Ultra-Fast Liquid Chromatography (UFLC) with Photo Diode Array (PDA) detection. Kinetic parameters such as rate constant k and the degradation rate of pesticides DT50 have been calculated using Pesticide Residue Dissipation Data. The findings showed that the tested fungicides degenerate according to pseudo-first-order kinetics. Based on the findings, we concluded that photocatalytic degradation of pesticides in soils are faster than photolysis. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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13 pages, 5018 KiB

Open AccessArticle

Synthesis of a Novel Hydrazone of Thieno[2,3-d]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations

by Mezna Saleh Altowyan, Matti Haukka, Saied M. Soliman, Assem Barakat, Ahmed T. A. Boraei and Manar Sopaih

Crystals 2023, 13(3), 384; https://doi.org/10.3390/cryst13030384 - 23 Feb 2023

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Abstract

The novel hydrazone-containing thieno[2,3-d]pyrimidine, namely, N′-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazide 4 was synthesized in a very good yield from the reaction of the triketoester 1 or ninhydrin 2 with the exocyclic acetohydrazide 3 in methanol. Good-quality crystals of [...] Read more.

The novel hydrazone-containing thieno[2,3-d]pyrimidine, namely, N′-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazide 4 was synthesized in a very good yield from the reaction of the triketoester 1 or ninhydrin 2 with the exocyclic acetohydrazide 3 in methanol. Good-quality crystals of 4 were obtained by recrystallization of the compound from the DMF/MeOH solvent mixture. The target product 4 crystallized in the triclinic crystal system and P-1 space group. The topology analysis of molecular packing indicated that the H…H (30.4%), O…H (22.0%) and H…C (17.0%) contacts are the most dominant intermolecular interactions in the crystal of 4, while the O…H, N…H, H…C, N…C, O…C, C…C and O…O are the only contacts which have shorter interaction distances than the vdWs radii sum of the interacting atoms. The structure of 4 is optimized and the calculated structure showed good agreement with the experimental one. Additionally, MEP, HOMO, LUMO and the reactivity descriptors were calculated. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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12 pages, 2807 KiB

Open AccessArticle

Synthesis and Computational Investigations of New Thioether/Azomethine Liquid Crystal Derivatives

by Alaa Z. Omar, Mohamed A. El-Atawy, Mai S. Alsubaie, Mohammed L. Alazmi, Hoda A. Ahmed and Ezzat A. Hamed

Crystals 2023, 13(3), 378; https://doi.org/10.3390/cryst13030378 - 23 Feb 2023

Cited by 10 | Viewed by 1534

Abstract

Methylthio moiety was observed to alter the mesomorphic features of rod-like Schiff-base-derived liquid crystalline materials. For this purpose, a new series of (E)-4-(alkoxy)-N-(4-(methylthio)benzylidene)aniline (I_n) liquid crystals were synthesized and examined using experimental and computational approaches. The [...] Read more.

Methylthio moiety was observed to alter the mesomorphic features of rod-like Schiff-base-derived liquid crystalline materials. For this purpose, a new series of (E)-4-(alkoxy)-N-(4-(methylthio)benzylidene)aniline (I_n) liquid crystals were synthesized and examined using experimental and computational approaches. The compounds in the series differ from each other in the terminal alkoxy chain length that is attached to one end of the aromatic core. Various spectroscopic methods were used to verify the molecular structures of the produced derivatives. All compounds were checked for correct chemical structures using elemental analysis, FT-IR, ¹H-NMR, and ¹³C-NMR. Both a polarized optical microscope (POM) and a differential scanning calorimeter (DSC) were used in order to study the behavior of liquid crystals. Both tested compounds I₆ and I₈ have monotropic nematogenic properties while the longer chain derivative I₁₆ shows non-mesomorphic behavior. Computational studies were carried out using density functional theory (DFT) calculations to validate the experimental results. All of the analyzed compounds had their reactivity characteristics, dipole moments, and polarizability explained. Finally, in order to determine the chemical shape–mesomorphic property relationship, the present examined series was compared to other structurally comparable homologues. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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13 pages, 5870 KiB

Open AccessArticle

Synthesis and Characterizations of Novel Isatin-s-Triazine Hydrazone Derivatives; X-ray Structure, Hirshfeld Analysis and DFT Calculations

by Hessa H. Al-Rasheed, Sarah A. AL-khamis, Assem Barakat, Ayman El-Faham, Matti Haukka and Saied M. Soliman

Crystals 2023, 13(2), 305; https://doi.org/10.3390/cryst13020305 - 12 Feb 2023

Cited by 1 | Viewed by 2361

Abstract

A novel series of isatin-s-triazine hydrazone derivatives has been synthesized and reported herein. The synthetic methodology involved the reaction of s-triazine hydrazine precursors with isatin derivatives in the presence of CH₃COOH as a catalyst and EtOH as solvent [...] Read more.

A novel series of isatin-s-triazine hydrazone derivatives has been synthesized and reported herein. The synthetic methodology involved the reaction of s-triazine hydrazine precursors with isatin derivatives in the presence of CH₃COOH as a catalyst and EtOH as solvent to afford the corresponding target products 6a-e in high yields and purities. The characterization data obtained from elemental analysis, FT-IR, NMR (¹H- and ¹³C-) were in full agreement with the expected structures. Furthermore, an X-ray single crystal diffraction study of one of the target s-triazine hydrazone derivatives, 6c confirmed the structure of the desired compounds. It crystallized in the triclinic crystal system and P-1 space group with a = 10.3368(6) Å, b = 11.9804(8) Å, c = 12.7250(5) Å, α = 100.904(4)°, β = 107.959(4)° and γ = 109.638(6)°. The different non-covalent interactions which contributed in the molecular packing of 6c were analyzed using Hirshfeld analysis. The molecular packing of the organic part of the crystal structure showed important O…H (7.1%), C…H (16.4%), C…C (1.6%), H…H (34.8%), N…H (8.0%) and C…N (4.0%) interactions while for the crystal solvent, the O…H (21.3%), H…H (61.2%) and N…H (8.1%) contacts are the most significant. The studied compound 6c is polar and has a net dipole moment of 5.6072 Debye based on DFT study. Full article

(This article belongs to the Special Issue Schiff Base Derivatives: Synthesis, Crystal Structure, Applications, Hirshfeld Surface Analysis)

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