3-Phenylisoxazolin-5-one: a redetermination

Essaghouani, Abdelhanine; Boulhaoua, Mohammed; Ouasif, L. El; Sebbar, Nada Kheira; Essassi, El Mokhtar; Mague, Joel T.

doi:10.1107/s2414314617000323

Cited by 2 publications

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“…According to their results, the compound behaved as an efficient inhibitor with IE of 97% at 10 −3 M. The IEs of two synthesized 1,5‐benzodiazepine derivatives against carbon steel corrosion in 1 M hydrochloric acid were studied. These compounds showed IE of 89% and 94% at 10 −3 M. [ 20 ] Essaghouani et al [ 21 ] studied the corrosion inhibition properties of 1‐ethyl‐4‐phenyl‐2,3‐dihydro‐1 H ‐1,5‐benzodiazepin‐2‐one for mild steel in 1 M hydrochloric acid. According to their results, the compound showed IE of 92% at 10 −3 M.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, several benzodiazepine derivatives were investigated as corrosion inhibitors in an acidic medium. [18][19][20][21] Sikine et al [18] investigated 1H-benzo[b] [1,4]diazepine-2,4(3H,5H)-dione as a corrosion inhibitor for mild steel in 1 M hydrochloric acid. The results of the study showed good corrosion inhibition performance of the studied compound with inhibition efficiency (IE) of 92% at a concentration of 10 −3 M. El Aoufir et al [19] evaluated 1,5-benzodiazepine derivative, namely, 4Z-(2-oxopropyl)-1,3-bis(prop-2-yn-1-yl)-2,3,4,5-tetrahydro-1,5-benzodiazepin-2-one, as a corrosion inhibitor for carbon steel in 1 M hydrochloric acid.…”

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confidence: 99%

“…), O(15), C(14), O(22), N(11), and C(9). Similarly, the atoms with the highest negative charges for methylBBD are O(21), N(7), O(22), C(20), C(14), N(11), and C(9), and for chloroBBD are O(13), N(7), C(12), O(22), N(11), and C (9) atoms. These atoms with the higher negative charge tend to donate electrons to the d-orbital of the Fe atom on the mild steel surface.…”

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Effect of substituents on the inhibitive properties of newly synthesized 5‐benzoyl‐4‐methyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐one derivatives against mild steel corrosion in an acidic medium

Al-Fakih

Al-Maqtari

Aziz

et al. 2020

Materials & Corrosion

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Inhibition performance of three newly synthesized 1,5-benzodiazepine derivatives with 4-methoxybenzoyl (methoxyBBD), 3-methylbenzoyl (methylBBD), and 2-chlorobenzoyl (chloroBBD) groups was investigated against mild steel corrosion in 1 M hydrochloric acid. The potentiodynamic polarization, electrochemical impedance spectroscopy, and adsorption isotherms were used for characterization of the corrosion processes. Surface morphology was studied by scanning electron microscope (SEM). Quantum chemical calculations were carried out to establish the active sites of the inhibitors. The results show that the inhibitors inhibit mild steel corrosion and their inhibition efficiencies (IE) increase with the increase in concentration. The methoxyBBD shows a higher inhibiting effect with IE of 89.13% at 10 −3 M, followed by methylBBD. All three inhibitors act as mixed-type inhibitors with predominant control of cathodic reaction for chloroBBD and their adsorption obeys Langmuir isotherm. The SEM analysis confirms the inhibitors' adsorption on the mild steel surface. The active sites of the inhibitors were effectively established using the density functional theory method on the basis of natural atomic charge, highest occupied molecular orbital, and the lowest unoccupied molecular orbital frontier molecular orbitals. The experimental and quantum results prove the inhibition performance trend of the inhibitors as follows: methoxyBBD > methylBBD > chloroBBD.

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Effect of substituents on the inhibitive properties of newly synthesized 5‐benzoyl‐4‐methyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐one derivatives against mild steel corrosion in an acidic medium

Al-Fakih

Al-Maqtari

Aziz

et al. 2020

Materials & Corrosion

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Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 4-(furan-2-yl)-2-(6-methyl-2,4-dioxopyran-3-ylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

et al. 2021

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The title compound {systematic name: (S,E)-3-[4-(furan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-2-ylidene]-6-methyl-2H-pyran-2,4(3H)-dione}, C19H16N2O4, is constructed from a benzodiazepine ring system linked to furan and pendant dihydropyran rings, where the benzene and furan rings are oriented at a dihedral angle of 48.7 (2)°. The pyran ring is modestly non-planar [largest deviation of 0.029 (4) Å from the least-squares plane] while the tetrahydrodiazepine ring adopts a boat conformation. The rotational orientation of the pendant dihydropyran ring is partially determined by an intramolecular N—HDiazp...ODhydp (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bond. In the crystal, layers of molecules parallel to the bc plane are formed by N—HDiazp...ODhydp hydrogen bonds and slipped π–π stacking interactions. The layers are connected by additional slipped π–π stacking interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (46.8%), H...O/O...H (23.5%) and H...C/C...H (15.8%) interactions, indicating that van der Waals interactions are the dominant forces in the crystal packing. Computational chemistry indicates that in the crystal the N—H...O hydrogen-bond energy is 57.5 kJ mol−1.

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3-Phenylisoxazolin-5-one: a redetermination

Cited by 2 publications

References 7 publications

Effect of substituents on the inhibitive properties of newly synthesized 5‐benzoyl‐4‐methyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐one derivatives against mild steel corrosion in an acidic medium

Effect of substituents on the inhibitive properties of newly synthesized 5‐benzoyl‐4‐methyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐one derivatives against mild steel corrosion in an acidic medium

Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 4-(furan-2-yl)-2-(6-methyl-2,4-dioxopyran-3-ylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

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