Synthesis, NMR characterization, DFT and anti-corrosion on carbon steel in 1M HCl of two novel 1,5-benzodiazepines

Sebhaoui, J.; Bakri, Youness El; Aoufir, Yasmina El; Anouar, El Hassane; Guenbour, A.; Nasser, Amal A.; Essassi, El Mokhtar

doi:10.1016/j.molstruc.2019.01.037

Cited by 36 publications

(19 citation statements)

References 27 publications

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“…It is easy to notice that Nyquist curves present a single capacitive loop over at frequency range from 10 mHz to 100 kHz, which is usually related to charge transfer phenomenon 45 . The capacitive plots are semicircles (imperfect circle), this is accredited to frequency spreading as a consequence of inhomogeneous behavior of electrode surface 46 . Increase in the diameter of semicircle on addition of DAEP1 and DAEP2 indicates that charge transfer phenomenon retorted or slow down due to adsorption of DAEPs at the interface of metal-electrolyte.…”

Section: Resultsmentioning

confidence: 99%

Epoxy pre-polymers as new and effective materials for corrosion inhibition of carbon steel in acidic medium: Computational and experimental studies

Dagdag

Safi

Hsissou

et al. 2019

Sci Rep

107

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Present study is designed for the synthesis, characterization and corrosion inhibition behavior of two diamine aromatic epoxy pre-polymers (DAEPs) namely, N 1 ,N 1 ,N 2 ,N 2 -tetrakis (oxiran-2-ylmethyl) benzene-1,2-diamine (DAEP1) and 4-methyl-N 1 ,N 1 ,N 2 ,N 2 -tetrakis (oxiran-2-ylmethyl) benzene-1,2-diamine (DAEP2) for carbon steel corrosion in acidic medium. Synthesized DAEPs were characterized using spectral (Nuclear magnetic resonance ( 1 H NMR) and Fourier transform infrared-attenuated total reflection (FTIR-ATR)) techniques. Viscosity studies carried out at four different temperatures (20–80 °C) increase in temperature causes significant reduction in their viscosities. The anticorrosive properties of DAEPs differing in the nature of substituents, for carbon steel corrosion in 1 M HCl solution was evaluated using several experimental and computational techniques. Both experimental and computational studies showed that inhibitor (DAEP2) that contains electron releasing methyl (-CH 3 ) showed higher protectiveness as compared to the inhibitor (DAEP1) without substituent (-H). Electrochemical results demonstrate that DAEPs act as reasonably good inhibitors for carbon steel in 1 M HCl medium and their effectiveness followed the sequence: DAEP2 (92.9%) > DAEP1 (91.7%). The PDP results show that the diamine aromatic epoxy pre-polymers molecules (DAEPs) act as mixed type inhibitors. Electrochemical study was also supported using scanning electron microscopy (SEM) method were significant improvement in the surface morphology of inhibited (by DAEPs) metallic specimens was obtained. Results derived from computational density functional theory (DFT) and molecular dynamics (MD) simulationsand studies were consistent with the experimental results derived from SEM, EIS and PDP electrochemical studies. Adsorption of the DAEPs obeyed the Langmuir adsorption isotherm model.

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Section: Resultsmentioning

confidence: 99%

Epoxy pre-polymers as new and effective materials for corrosion inhibition of carbon steel in acidic medium: Computational and experimental studies

Dagdag

Safi

Hsissou

et al. 2019

Sci Rep

107

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“…In continuation of our studies on functionalized heterocycles and our previous works on 1,5‐benzodiazepine derivatives, we report the synthesis, crystal structure and Hirshfeld surface analysis of 4‐phenyl‐decahydro‐1H‐1,5‐benzodiazepin‐2‐one ( 1 ) obtained by hydrogenation of 4‐phenyl‐5a,6,7,8,9,9a‐hexahydro‐1H‐1,5‐benzodiazepin‐2(5H)‐one in the presence of palladium on activated charcoal in anhydrous ethanol. (Scheme ).…”

Section: Introductionmentioning

confidence: 89%

Synthesis, Crystal Structure and Computational Investigation of New 4‐Phenyl‐decahydro‐1H‐1,5‐benzodiazepin‐2‐one as Potent Inhibitor of Mu‐opioid Receptor

Garadi¹,

Bakri

Lai

et al. 2020

ChemistrySelect

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A novel benzodiazepine derivative was prepared and characterized by elemental analysis, FT-IR, NMR ( 1 H and 13 C) and HR-MS methods. Its crystal structure was also investigated by single crystal X-ray diffraction. In the title compound, the fused 6-and 7-membered rings adopt chair and "twist boat" conformations, respectively. In the crystal, the molecules form inversion dimers through N-H⋅⋅⋅O hydrogen bonds and pack with no unusually short intermolecular contacts, which is in agreement with the results of the Hirshfeld surface analysis.The Hirshfeld surface analysis showed that the H⋅⋅⋅H contact was the most important interaction for the studied compound. Based on the DFTÀ B3LYP study, the studied compound owned a little different geometry in the gas phase concerning the solid phase. The molecular docking was performed between the title compound and a mu-opioid receptor. Molecular dynamics studies were also carried up to 50 ns to understand the stability for the title compound complex with the mu-opioid receptor.[a] Dr.

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“…Considerations of these features of corrosion inhibitors have led to the evaluations of numerous biological materials for effective corrosion inhibitors [11][12][13][14][15][16][17][18] due to their non-toxicity and biodegradable properties. Furthermore, novel ionic liquids [19][20][21] and some eco-friendly organic compounds containing different forms of functional groups, heteroaryl, aromatics cycles, saturated and unsaturated bonds in their molecular structures [22][23][24][25][26][27] have been reported as effective corrosion inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Impact of Degree of Hydrophilicity of Pyridinium Bromide Derivatives on HCl Pickling of X-60 Mild Steel: Experimental and Theoretical Evaluations

et al. 2020

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Dodecyl pyridinium bromide (DDPB), tetradecyl pyridinium bromide (TDPB) and dodecyl 1,1′-bispyridinium dibromide (DDBPB) were successfully synthesized, characterized and evaluated for HCl pickling of X-60 low carbon steel. Order of corrosion inhibitions efficiencies, as revealed by both electrochemical and gravimetric studies, is TDPB > DDPB > DDBPB. The degree of hydrophilicity of inhibitors as predicted by a partition coefficient (Log P) and supported by a contact angle measurement was found to be responsible for their order of corrosion inhibition efficiencies. Adsorption of DDPB, TDPB, and DDBPB through the pyridinium nitrogen on mild steel surface was confirmed by ATR-FTIR and SEM-EDX analyses. The pyridinium nitrogen was found not to be the only factor responsible for their efficiency, but hydrophobes and the orientation of the hydrophilic ring were responsible, which incline to the deviation of experimental results and the order of Monte Carlo simulation adsorption energies. DDPB, TDPB, and DDBPB obey the Langmuir isotherm model despite major contributions of the film formed on the surface of X-60 mild steel on their overall inhibition corrosion resistance.

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Synthesis, NMR characterization, DFT and anti-corrosion on carbon steel in 1M HCl of two novel 1,5-benzodiazepines

Cited by 36 publications

References 27 publications

Epoxy pre-polymers as new and effective materials for corrosion inhibition of carbon steel in acidic medium: Computational and experimental studies

Epoxy pre-polymers as new and effective materials for corrosion inhibition of carbon steel in acidic medium: Computational and experimental studies

Synthesis, Crystal Structure and Computational Investigation of New 4‐Phenyl‐decahydro‐1H‐1,5‐benzodiazepin‐2‐one as Potent Inhibitor of Mu‐opioid Receptor

Impact of Degree of Hydrophilicity of Pyridinium Bromide Derivatives on HCl Pickling of X-60 Mild Steel: Experimental and Theoretical Evaluations

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