DFT study of salicylaldehyde semicarbazone derivatives interaction with copper and the effect of aminic substituent

Tan, Shiow Jin; Xi, Hong Wei; Bedoura, Sultana; Lim, Kok Hwa

doi:10.1016/j.ica.2011.11.024

Cited by 4 publications

(4 citation statements)

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“…The quantum calculations, in particular density functional theory (DFT), are widely used in coordination chemistry not only to achieve a quantitative description of * Corresponding author. Email: sa_zarei@iausdj.ac.ir, Seyedamirzarei@yahoo.com chemical and physical features of different complexes but also to predict new physical and chemical features [16][17][18][19][20][21]. Rigamonti et al reported the DFT calculation of the copper complexes of some salen-type ligands to confirm the assignments of electronic absorption spectra and evaluate the NLO properties [22].…”

Section: Introductionmentioning

confidence: 99%

Copper(II) and nickel(II) complexes of tetradentate Schiff base ligand: UV-Vis and FT-IR spectra and DFT calculation of electronic, vibrational and nonlinear optical properties

et al. 2015

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The experimental fourier transform infrared (FT-IR) and ultraviolet-visible (UV-Vis) spectra of copper(II) and nickel(II) complexes of the deprotonated tetradentate Schiff base ligand N,N -bis(2-hydroxybenzylidene)-2,2-dimethyl-1,3-propanediamine (H 2 L) are compared with their corresponding theoretical ones. The applied theoretical method is based on the density functional theory and time-dependent density functional theory at the UPBE0/PBE0 levels using Def2-TZVP basis set. The computational optimised geometric parameters of the complexes are in good agreement with their corresponding experimental data. The FT-IR and UV-Vis spectra of the complexes were reproduced on the basis of their optimised structures. The vibrational assignments of some fundamental modes of the complexes are performed. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies are calculated. The analyses of the calculated electronic absorption spectra of the complexes are carried out to elucidate the electronic transitions assignments and their characters. Second-order nonlinear optical property of the complexes is evaluated by the above-mentioned theoretical method that implies much greater values for the complexes in comparison with the corresponding value of urea.

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Section: Introductionmentioning

confidence: 99%

Copper(II) and nickel(II) complexes of tetradentate Schiff base ligand: UV-Vis and FT-IR spectra and DFT calculation of electronic, vibrational and nonlinear optical properties

et al. 2015

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“…The relative stability of salicylaldehyde semicarbazone derivatives has been previously investigated by Xi et al [29]. They have compared the theoretic and experimental results to confirm the stability order of conformers.…”

Section: Introductionmentioning

confidence: 99%

Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

et al. 2015

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New series of 2-(aryl or alkyl)-N-phenylhydrazine-1-carboxamides 1a-j were synthesized through one-pot reactions of aldehyde or ketones, hydrazine hydrate, and phenylisocyanate in MeOH. The structure of products was confirmed by Fourier transform infrared (FT-IR), proton nuclear magnetic resonance ( 1 H NMR), and 13 C NMR spectra. Minimum inhibitory concentration (MIC) of antibacterial activity of 1a-j was screened against five bacterial strains. Compound 1f showed antibacterial activity against Pseudomonas aeruginosa and Staphylococcus aureus.

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“…Attempts to prepare benzotriazepinone from unsubstituted semicarbazone 15 were unsuccessful using similar conditions; instead, ions corresponding to oligomer were detected by HPLC–MS analysis of the reaction mixture. Semicarbazone alkylation may favor cyclization by lowering the barrier for urea isomerization to the required E -isomer . α-Alkyl-branched ketones 18 reacted slower in the cyclization to 6 , likely because the neighboring ketone is engaged in a hydrogen bond with the aniline NH that disfavors the orientation for nuclophilic attack .…”

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confidence: 99%

“…Semicarbazone alkylation may favor cyclization by lowering the barrier for urea isomerization to the required Eisomer. 19 α-Alkyl-branched ketones 18 reacted slower in the cyclization to 6, likely because the neighboring ketone is engaged in a hydrogen bond with the aniline NH that disfavors the orientation for nuclophilic attack. 20 The favored hydrogen bonded conformer was illustrated in a comparison of 16h and 18l in deuterium exchange NMR experiments using MeOD-d 4 in CDCl 3 .…”

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confidence: 99%

Chemoselective Alkylation for Diversity-Oriented Synthesis of 1,3,4-Benzotriazepin-2-ones and Pyrrolo[1,2][1,3,4]benzotriazepin-6-ones, Potential Turn Surrogates

Douchez

Lubell

2015

Org. Lett.

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1,3,4-Benzotriazepin-2-ones garner interest for medicinal applications, in part due to their relationship with benzodiazepinones. Ten 1,3,4-benzotriazepin-2-ones 6 and 19 and six pyrrolo[1,2][1,3,4]benzotriazepin-6-ones 7 and 23 were prepared in four to seven steps and 4-60% overall yields by a divergent strategy from methyl anthranilate employing chemoselective alkylations of common linear and cyclic precursors to diversify three triazepinone ring positions (N1, N3, and C5). X-ray crystallography demonstrated that benzotriazepinone 19g may serve as a γ-turn mimic.

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DFT study of salicylaldehyde semicarbazone derivatives interaction with copper and the effect of aminic substituent

Cited by 4 publications

References 28 publications

Copper(II) and nickel(II) complexes of tetradentate Schiff base ligand: UV-Vis and FT-IR spectra and DFT calculation of electronic, vibrational and nonlinear optical properties

Copper(II) and nickel(II) complexes of tetradentate Schiff base ligand: UV-Vis and FT-IR spectra and DFT calculation of electronic, vibrational and nonlinear optical properties

Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

Chemoselective Alkylation for Diversity-Oriented Synthesis of 1,3,4-Benzotriazepin-2-ones and Pyrrolo[1,2][1,3,4]benzotriazepin-6-ones, Potential Turn Surrogates

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