Computational, spectroscopic, Hirshfeld surface, electronic state and molecular docking studies on phthalic anhydride

Fatima, Aysha; Khanum, Ghazala; Sharma, Arun; Garima, Km.; Savita, Sandhya; Verma, Indresh; Siddiqui, Nazia; Javed, Saleem

doi:10.1016/j.molstruc.2021.131571

Cited by 26 publications

(9 citation statements)

References 55 publications

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“…When compared with the recently reported phthalic anhydride containing studies, C–O double bond lengths appear to be in agreement with the values in this study. 38 , 39 …”

Section: Resultsmentioning

confidence: 99%

Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride

et al. 2022

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We report a novel anhydride derivative, 3-acetoxy-2-methylbenzoic anhydride (AMA), obtained from the interaction of 3-acetoxy-2-methylbenzoyl chloride with 3-acetoxy-2-methylbenzoic acid. The synthesized compound was characterized by elemental analysis, IR, 1 H NMR, and 13 C NMR spectroscopic studies and single-crystal X-ray crystallography which revealed the crystallization of AMA as monoclinic with space group P 2 1 / c . A Hirshfeld surface analysis was performed to record various intermolecular interactions, indicating the stabilization of the AMA structure by the intermolecular weak C–H···O hydrogen bonds and π···π interactions. The title compound was screened for antibacterial and antifungal activities using a serial dilution technique under aseptic conditions. The results indicate that the title compound has significant antibacterial properties but showed no antifungal behavior.

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“…When compared with the recently reported phthalic anhydride containing studies, C–O double bond lengths appear to be in agreement with the values in this study. 38 , 39 …”

Section: Resultsmentioning

confidence: 99%

Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride

et al. 2022

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“…Synthesis of new chemical compounds and evaluation of their biological properties are the main tasks in organic medicinal chemistry research. A literature survey revealed that several heterocyclic compounds originating from cyclic acid anhydrides have made a great contribution in a number of interesting areas [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ]. Cyclic acid anhydrides (phthalic, naphthalic, pyromellitic, and maleic acids, etc.)…”

Section: Introductionmentioning

confidence: 99%

“…are considered to be building blocks in the construction of many scaffolds with different applications in chemical and pharmaceutical fields. For instance, they are essential in plastic synthetic resins (glyptal, alkyd, polyester), polyurethane, household appliances, and medical device coatings, and are used as key intermediates in phthalein, rhodamine, phthalocyanine, anthraquinone, fluorescein, and agrochemical production [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ]. Moreover, many cyclic anhydride derivatives participate in the building of additional bioactive compounds with plethora of biological activities, including antiviral, antitumor, immunomodulatory, cytotoxic, and antimicrobial agents [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ] ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

“…Phthalic anhydride, known as 2-benzofuran-1,3-dione, is characterized by oxygen-rich atoms and was first made commercially available as dicarboxylic acid anhydride. It is synthesized from phthalic acid dehydration reaction or can be obtained via Diels–Alder cycloaddition of furan and maleic anhydride followed by dehydration [ 2 , 18 ]. Phthalic anhydrides are widely used in the chemical industry, with one major application in the production of several phthalate esters which are widely used in the plastics industry as plasticizers.…”

Section: Introductionmentioning

confidence: 99%

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Reactivity of 4,5-Dichlorophthalic Anhydride towards Thiosemicarbazide and Amines: Synthesis, Spectroscopic Analysis, and DFT Study

et al. 2022

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The cyclic anhydrides are broadly employed in several fields, such as the chemical, plastic, agrochemical, and pharmaceutical industries. This study describes the chemical reactivity of 4,5-dichlorophthalic anhydride towards several nucleophiles, including thiosemicarbazide and different amines, to produce the carboxylic acid derivatives resulting from anhydride’s opening, namely, phthalimide and dicarboxylic acid (1–12) products. Their chemical structures are confirmed by NMR, IR and MS spectra analyses. Density–functional theory (DFT) studies are performed using (DFT/B3LYP) with the 6-311G(d, p) basis sets to recognize different chemical and physical features of the target compounds.

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“…The Molecular Electrostatic Potential provides a qualitative estimate of the molecule reactive area, whereas Fukui function analysis provides a quantitative estimate. Molecular docking experiments are used to find the interaction of ligand (21HBMBA) with a suitable protein downloaded from RSCPDB site; these proteins may be transferase, kinase, hydrolase, oxidoreductase, Hydrolase, lyase/dehydratase, or hydroxylase domains [20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Vibrational Spectroscopy, Quantum Computational and Molecular Docking Studies on 2-[(1H-Benzimidazol-1-yl)-methyl]benzoic Acid

et al. 2022

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Experimental and theoretical investigations on the optimized geometrical structure, electronic and vibrational features of 2-[(1H-benzimidazol-1-yl)-methyl]benzoic acid are provided using the B3LYP/6-311++G(d,p) basis set. The Vibrational Energy Distribution Analysis (VEDA) program was used to perform the vibrational assignments and calculate the Potential Energy Distribution (PED). The acquired FT-IR and FT Raman data were used to complete the vibrational assignment and characterization of the compound fundamental modes. Theoretical and actual NMR chemical shifts were found to be quite similar. The UV-vis spectrum of 21HBMBA, as well as effects of solvents, have been investigated. The calculated HOMO and LUMO energies reveal that charge transfer happens within the molecule and MEP surface to be a chemically reactive area appropriate for drug action. Furthermore, a thorough examination of Non-Bonding Orbitals, excitation energies, AIM charges, Fukui functions and the Electron Localization Function (ELF) is carried out. The research is also expanded to compute first-order hyperpolarizability and forecast NLO characteristics. The details of the docking studies aided in the prediction of protein binding.

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Computational, spectroscopic, Hirshfeld surface, electronic state and molecular docking studies on phthalic anhydride

Cited by 26 publications

References 55 publications

Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride

Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride

Reactivity of 4,5-Dichlorophthalic Anhydride towards Thiosemicarbazide and Amines: Synthesis, Spectroscopic Analysis, and DFT Study

Vibrational Spectroscopy, Quantum Computational and Molecular Docking Studies on 2-[(1H-Benzimidazol-1-yl)-methyl]benzoic Acid

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