Me<sub>3</sub>N-promoted synthesis of 2,3,4,4a-tetrahydroxanthen-1-one: preparation of thiosemicarbazone derivatives, their solid state self-assembly and antimicrobial properties

Hameed, Aminah; Shafiq, Zahid; Yaqub, Muhammad; Hussain, Mazhar; Hussain, Muhammad Ajaz; Afzal, Muhammad; Tahir, Muhammad Nawaz; Naseer, Muhammad Moazzam

doi:10.1039/c5nj01879j

Cited by 27 publications

(7 citation statements)

References 47 publications

(49 reference statements)

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“…The formation of this preferred conformation is attributed to comparatively stronger intramolecular hydrogen bonding in 3a [N(1)–H(1)···N(3) 2.226 Å (conformer A) and N(4)–H(4E)···N(6) 2.211 Å (conformer B)] and in 3b [N(3)–H(3A)···N(1) 2.234]. Notably, these findings are in complete agreement with our previously reported similar compounds. − …”

Section: Methodssupporting

confidence: 90%

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

et al. 2020

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By the condensation of thiosemicarbazide with coumarin aldehyde, two novel substituted thiosemicarbazones with chemical formulae C24H25N3O3S (3a) and C26H23N3O3S (3b) have been synthesized. The synthesized compounds were resolved using SC-XRD, and structure elucidation was carried out using 1H NMR, 13C NMR, UV–visible, and FT-IR spectroscopic analyses. Computational calculations at the B3LYP/6-311+G(d,p) level of theory were performed to countercheck the experimental (UV–vis, FT-IR) findings and explore the electronic (FMO, NBO, MEP) properties of 3a–b. The nonlinear optical (NLO) properties of 3a–b were estimated using B3LYP, HF, LC-BLYP, CAM-B3LYP, M062X, and M06 functionals in combination with the 6-311+G(d,p) basis set. The crystallographic data revealed that compounds were crystallized as an orthorhombic crystal lattice with the Pbcn space group and the triclinic crystal lattice with the P̅1 space group. A good concurrence among experimental SC-XRD-generated bond lengths, bond angles, FT-IR, UV–vis, and corresponding DFT results was found, which confirms the purity of both compounds. The NBO analysis confirmed the presence of intramolecular hydrogen bonding and hyperconjugative interactions, which not only were the pivotal cause of stability of the investigated compounds but also led to an overwhelming NLO response. The energy differences calculated for HOMO/LUMO are 3.053 and 3.118 eV in 3a and 3b, respectively. The crystal 3b showed a higher value of first-order polarizability at all levels of theory than 3a. Overall results show that the crystals under investigation are polarized in nature with a good dipole moment. A comparative analysis with urea molecules clearly indicates that the studied compounds are acceptable NLO candidates and they can be used for future technological applications.

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Section: Methodssupporting

confidence: 90%

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

et al. 2020

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“…Nowadays, finding solutions to clean the water contaminated by dyes is prime focus of research. At the same time, synthesis of bactericidal materials 1 is equally significant for cleaning infected water, food packaging, hospital implants, and dentistry instruments. [2][3][4][5] Furthermore, in the health sector, cancer is the most threatening and incurable disease known till now.…”

Section: Introductionmentioning

confidence: 99%

Graphene/SiO2 nanocomposites: The enhancement of photocatalytic and biomedical activity of SiO2 nanoparticles by graphene

Arshad

Iqbal

Mansoor

et al. 2017

Journal of Applied Physics

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ABSTRACT:The exceptional conducting nature of graphene makes it a viable candidate for enhancing the effectiveness of photocatalytic and biomedical nanomaterials. Herein, the immobilization of monodispersed silicon dioxide (SiO2) nanoparticles on multiple graphene layers is demonstrated for intercalation of graphene nanoplatelets (GNPs). Interestingly, the loading of graphene nanoplatelets with SiO2 nanoparticles enhances the photocatalytic efficiency from 46% to 99%. For biomedical applications, it is found that 75% of Gram positive and 50% of Gram negative bacteria have been killed, hence bacterial proliferation is significantly restricted. Further, the cytotoxicity study reveals that the synthesised nanocomposites are non-toxic for both normal (HCEC) and cancerous (MCF-7, HEp-2) cell lines which signifies their potential as carriers for drug delivery. The prepared nanocomposites with controlled amount of carbon in the form of graphene can be employed for photocatalysis based waste water remediation, biomedicine and nano drug delivery.

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“…In the solid state packing, the amide moiety in both benzoimidazole‐based hydrazones 5a and 5b adopt cis‐conformation, providing the possibility of appearance of a centrosymmetric amide dimer

R_{2}^{2} ((), 8)

{···H–N–C=O} 2 synthon. However, this dimeric synthon appeared in only compound 5a [(N(3)‐H(3)···O(1) 2.088 Å], facilitated by centrosymmetric CH···O interactions [(C(17)‐H(17C)···O(1) 2.353 Å] (Figure a) .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

Rafiq

Khalid

Tahir

et al. 2019

Applied Organom Chemis

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Present study advocates the joint experimental and computational studies of two potent benzoimidazole-based hydrazones with chemical formula C 23 H 18 F 2 N 4 O (5a) and C 25 H 22 FN 5 O 3 (5b). Both 5a and 5b were synthesized and resolved into their crystal structures using SC-XRD for the assessment of bond lengths, bond angles, unit cells and space groups. The structures of 5a and 5b were chemically characterized using infrared (FT-IR), UV-Visible, nuclear magnetic resonance ( 1 H-NMR and 13 C-NMR), EIMS and elemental analysis. DFT at M06-2X/6-31G(d,p) level of theory was performed to get optimized structures and countercheck the experimental findings. Overall, DFT findings show excellent concurrence with the experimental data which confirms the purity of both compounds. FMO, NBO analysis, MEP surfaces and nonlinear optical (NLO) properties were explored at same level of theory. UV-Vis analysis at TDDFT/M06-2X/6-31G(d,p) level of theory showed that 5b is red shifted with λ max 331.69 nm as compared to 5a with λ max 240.25 nm. Global reactivity parameters were estimated using energy of FMOs indicated the greater harness value than the softness values of 5a and 5b. NBO analysis confirmed that the presence of non-covalent interactions, hydrogen bonding and hyper conjugative interactions are pivotal cause for the existence of 5a and 5b in the solid-state. NLO results of 5a and 5b were observed better than standard molecule recommended the NLO activity of said molecules for optoelectronic applications. Highlights• Two novel benzoimidazole-based hydrazones were synthesized.• XRD, NMR, FT-IR, UV-Vis, EIMS and elemental analysis were performed for the characterization.

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Me₃N-promoted synthesis of 2,3,4,4a-tetrahydroxanthen-1-one: preparation of thiosemicarbazone derivatives, their solid state self-assembly and antimicrobial properties

Abstract: Thiosemicarbazones (5a–5j) have been synthesized from 2,3,4,4a-tetrahydroxanthen-1-one, obtained in high yield through Me3N-promoted domino Baylis–Hillman/oxa-Michael reaction. Their solid-state self-assembly and antimicrobial properties are studied.

Cited by 27 publications

References 47 publications

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

Graphene/SiO2 nanocomposites: The enhancement of photocatalytic and biomedical activity of SiO2 nanoparticles by graphene

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

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Me3N-promoted synthesis of 2,3,4,4a-tetrahydroxanthen-1-one: preparation of thiosemicarbazone derivatives, their solid state self-assembly and antimicrobial properties

Abstract: Thiosemicarbazones (5a–5j) have been synthesized from 2,3,4,4a-tetrahydroxanthen-1-one, obtained in high yield through Me3N-promoted domino Baylis–Hillman/oxa-Michael reaction. Their solid-state self-assembly and antimicrobial properties are studied.

Cited by 27 publications

References 47 publications

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

Graphene/SiO2 nanocomposites: The enhancement of photocatalytic and biomedical activity of SiO2 nanoparticles by graphene

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

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Me₃N-promoted synthesis of 2,3,4,4a-tetrahydroxanthen-1-one: preparation of thiosemicarbazone derivatives, their solid state self-assembly and antimicrobial properties