Mercuration and Telluration of 2-Fluoro-5-nitroaniline: Synthesis, Antibacterial, and Computational Study

Al-Asadi, Rafid H.; Mohammed, Mustafa K. A.; Dhaef, Hawraa Kareem

doi:10.1134/s1070363220040222

Cited by 8 publications

(3 citation statements)

References 22 publications

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“…It stands for the energy difference between the lower virtual energy level and the higher full energy level [29], see Fig. (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) and Table 3.…”

Section: Electronic Propertiesmentioning

confidence: 99%

“…In the last ten years, considerable development of organic tellurium chemistry has been observed, and several review articles and books on the subject have been published, focusing on the general reactions used to prepare the organotellurium compounds and the useful synthetic transformations promoted or suffered by them [2][3][4][5]. Recently, emphasis has been given to the recent contributions of the related laboratory where they explored old reactions trying to establish their generality or make transformations into the organotellurium compounds, which can lead to applicable synthetic methodologies [4,[6][7][8][9][10][11]. The quantum mechanical wave function contains all the information about the studied system.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Theoretical Studies of New Organotellurium Compounds Based on (4-(((1S,E)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II) Chloride

Al-Saadawy

2021

Indones. J. Chem.

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The current study aimed to prepare new organomercury and organotellurium compounds based on the condensation reaction of 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (camphor) and p-aminophenyl mercuric(II) chloride. All the prepared compounds were characterized using different methods such as infrared spectrum, nuclear magnetic resonance, and CHN analysis. The analysis results concurred with the suggested chemical structures of the prepared compounds. Density functional theory has been applied with the basis set 3-21G to investigate the molecular structure of the prepared organotellurium compounds. Geometrical structure, HOMO surfaces, LUMO surfaces, and energy gap have been produced throughout the geometry optimization. The molecular geometry and contours for organotellurium compounds have been investigated throughout the geometrical optimization. Also, the donor and acceptor have been studied by comparing the HOMO energies of the prepared organotellurium compounds. Finally, the electronegativity, electrophilicity, ionization potential, electron affinity, and lower case of organotellurium compounds have been calculated and discussed.

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“…It stands for the energy difference between the lower virtual energy level and the higher full energy level [29], see Fig. (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) and Table 3.…”

Section: Electronic Propertiesmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Characterization and Theoretical Studies of New Organotellurium Compounds Based on (4-(((1S,E)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II) Chloride

Al-Saadawy

2021

Indones. J. Chem.

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“…Synthesising several organotellurium compounds using transmetallation of organomercury substances has been widely studied and reported in several publications [4][5][6][7]. Aromatic compounds, when reacting with tellurium tetrahalides, undergo a direct substitution reaction, and the obtained yield is low.…”

Section: Introductionmentioning

confidence: 99%

New Mercurated and Tellurated Sulpha Compounds: Synthesis, Invitro Anticancer Study and DFT Calculation.

2021

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The current study includes mercuration and telluration of some sulpha compounds; these compounds were prepared by reaction of 4-aminobenzenesulfonic acid and 4,4'-sulfonyldianiline with mercuric(II) acetate reagent to produce Arylmercuric(II)chloride, which was subjected to transmetallation reactions by using TeBr4 to form the Aryltellurium(IV) tribromide. Additionally, the reactions between (2-amino-5-sulfophenyl)mercury(II) chloride and 3,4-dihydroxybenzaldehyde on one hand, and 4,4'-sulfonylbis[2-chloromercuric aniline] with benzaldehyde, on the other, produce mercurated sulpha compounds containing azomethine-group. These obtained compounds react with TeBr4 to form new tellurated sulpha compounds containing azomethine-group. These newly created compounds were subjected to various analyses, including C.H.N.S analysis, proton-NMR, FT-IR, and Carbon-13 NMR. The synthesised compounds were tested for cytotoxicity using in-vitro analyses on two human cancer cell lines, PC3 (prostate cancer cell) and T24 (bladder cancer cell). The prepared organotellurium compounds are effective, especially 4 and 6 compounds. DFT calculations of HOMO and LUMO energy levels and certain quantum parameters indicate that the organomercury compounds are relatively stable and exhibit lesser reactivity when compared to their organotellurium counterparts. Additionally, theoretical results validate the results obtained by the measurement of cancer effectiveness.

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Synthesis and characterization of [4‐{(CH₂O)₂CH}C₆H₄]₂Hg, [4‐(O=CH)C₆H₄]₂Hg and [(E)‐4‐(RN=CH)C₆H₄]₂Hg (R = 2′‐py, 4′‐py, 2′‐pyCH₂, 4′‐pyCH₂)

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et al. 2021

Applied Organom Chemis

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The reaction of 4‐[(CH2O)2CH]C6H4Br (1) with n‐BuLi, followed by addition of HgCl2 to the in situ formed organolithium derivative, affords [4‐{(CH2O)2CH}C6H4]2Hg (2). Deprotection of the formyl groups of 2 in presence of p‐TsOH (p‐Ts = 4‐MeC6H4SO3) leads to [4‐(O=CH)C6H4]2Hg (3). Condensation reactions of 3 with 2‐aminopyridine (2‐pyNH2), 4‐aminopyridine (4‐pyNH2), 2‐aminomethylpyridine (2‐pyCH2NH2), and 4‐aminomethylpyridine (4‐pyCH2NH2), in CH2Cl2, affords the novel diorganomercury(II) compounds of type [(E)‐4‐(RN=C)C6H4]2Hg [R = 2′‐py (4), 4′‐py (5), 2'‐pyCH2‐ (6), 4′‐pyCH2 (7)]. Compounds 2 and 3 were useful precursors for the preparation of the corresponding homocoupling products [4‐{(CH2O)2CH}C6H4]2 (8) and [4‐(O=CH)C6H4]2 (9) in presence of catalytic amounts of palladium(II) acetate. Compounds 2–9 were characterized by multinuclear magnetic resonance (NMR) (1H, 13C{1H}, and 199Hg{1H}, when appropriate) and infrared (IR) spectroscopy and by mass spectrometry. The molecular structures of 3, 5, 6, 8, and 9 were determined by single‐crystal X‐ray diffraction.

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Mercuration and Telluration of 2-Fluoro-5-nitroaniline: Synthesis, Antibacterial, and Computational Study

Cited by 8 publications

References 22 publications

Synthesis, Characterization and Theoretical Studies of New Organotellurium Compounds Based on (4-(((1S,E)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II) Chloride

Synthesis, Characterization and Theoretical Studies of New Organotellurium Compounds Based on (4-(((1S,E)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II) Chloride

New Mercurated and Tellurated Sulpha Compounds: Synthesis, Invitro Anticancer Study and DFT Calculation.

Synthesis and characterization of [4‐{(CH₂O)₂CH}C₆H₄]₂Hg, [4‐(O=CH)C₆H₄]₂Hg and [(E)‐4‐(RN=CH)C₆H₄]₂Hg (R = 2′‐py, 4′‐py, 2′‐pyCH₂, 4′‐pyCH₂)

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Mercuration and Telluration of 2-Fluoro-5-nitroaniline: Synthesis, Antibacterial, and Computational Study

Cited by 8 publications

References 22 publications

Synthesis, Characterization and Theoretical Studies of New Organotellurium Compounds Based on (4-(((1S,E)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II) Chloride

Synthesis, Characterization and Theoretical Studies of New Organotellurium Compounds Based on (4-(((1S,E)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II) Chloride

New Mercurated and Tellurated Sulpha Compounds: Synthesis, Invitro Anticancer Study and DFT Calculation.

Synthesis and characterization of [4‐{(CH2O)2CH}C6H4]2Hg, [4‐(O=CH)C6H4]2Hg and [(E)‐4‐(RN=CH)C6H4]2Hg (R = 2′‐py, 4′‐py, 2′‐pyCH2, 4′‐pyCH2)

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Synthesis and characterization of [4‐{(CH₂O)₂CH}C₆H₄]₂Hg, [4‐(O=CH)C₆H₄]₂Hg and [(E)‐4‐(RN=CH)C₆H₄]₂Hg (R = 2′‐py, 4′‐py, 2′‐pyCH₂, 4′‐pyCH₂)