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A cinnamaldehyde Schiff base of S-(4-methyl-benz-yl) di-thio-carbazate: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The title di-thio-carbazate ester (I), C₁₈H₁₈N₂S₂ [systematic name: (E)-4-methyl-benzyl 2-[(E)-3-phenyl-allyl-idene]hydrazinecarbodi-thio-ate, comprises an almost planar central CN₂S₂ residue [r.m.s. deviation = 0.0131?Å]. The methyl-ene(tolyl-4) group forms a dihedral angle of 72.25?(4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586?Å] so the mol-ecule approximates mirror symmetry with the 4-tolyl group bis-ected by the plane. The configuration about both double bonds in the N-N=C-C=C chain is E; the chain has an all trans conformation. In the crystal, eight-membered centrosymmetric thio-amide synthons, {?HNCS}₂, are formed via N-H?S(thione) hydrogen bonds. Connections between the dimers via C-H?? inter-actions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an inter-action profile similar to that of a closely related analogue with an S-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connected via N-H?S hydrogen bonds is about 0.94 kcal mol^-1 more stable than that in (I).

SUBMITTER: Yusof ENM

PROVIDER: S-EPMC5382618 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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A cinnamaldehyde Schiff base of S-(4-methyl-benz-yl) di-thio-carbazate: crystal structure, Hirshfeld surface analysis and computational study.

Yusof Enis Nadia Md ENM Tahir Mohamed I M MIM Ravoof Thahira B S A TBSA Tan Sang Loon SL Tiekink Edward R T ERT

Acta crystallographica. Section E, Crystallographic communications 20170321 Pt 4

The title di-thio-carbazate ester (I), C18H18N2S2 [systematic name: (E)-4-methyl-benzyl 2-[(E)-3-phenyl-allyl-idene]hydrazinecarbodi-thio-ate, comprises an almost planar central CN2S2 residue [r.m.s. deviation = 0.0131 Å]. The methyl-ene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the mol-ecule approximates mirror sy ...[more]

PMID: 28435717

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Project description:The inhibitory effect of di-imine-SB namely ((N1Z, N4E)-N1, N4-bis (4 (dimethylamino) benzylidene) butane 1,4-diamine) on X65-steel in 1 M HCl has been investigated experimentally and theoretically. The electrochemical impedance spectroscopy (EIS), potentiodynamic polarization (PDP), and weight loss outcomes display the anticorrosion properties of "di-imine- SB". The inhibitory efficiency exceeds 90% at the optimal concentration of 1 × 10-3 M "di-imine- SB". The metal surface was examined further using scanning electron microscope (SEM) and energy dispersive X-ray (EDX). The effectiveness of the di-imine-SB is returned into its adsorption on X65-steel surface and found in agreement with Langmuir adsorption isotherm. According to the standard Gibbs free energy of adsorption [Formula: see text], di-imine-SB adsorption tends to be chemical rather than physical, it increases the activation energy ([Formula: see text]) of metal dissolution reaction and makes it hard to occur. The PDP data suggested anodic and cathodic type of the di-imine-SB inhibitor. Meanwhile, increasing the resistance of X65-steel to 301 Ω cm2 after adding 1 mM of di-imine-SB confirms its protective effect. Whereas, the positive value of the fraction of electron transference (ΔN, 0.746), confirms the affinity of di-imine-SB to share electrons to the partially filed 3d-orbital of Fe forming strong protective film over X65-steel surface. Aided by Monte Carlo (MC) simulation, the calculated adsorption energy (Eads) suggests excessive adsorption affinity of di-imine-SB on metal surface over the corrosive chlorides and hydronium ions. A good correlation between the theoretical hypothesis and the experimental inhibition efficiency has been achieved. The comparative study showed the superior of the di-imine-SB as potential corrosion inhibitor compared with those reported before. Finally, global reactivity descriptors; electron affinity (A), ionization potential (I), electronegativity (χ), dipole moment (µ), global hardness ([Formula: see text]), electrophilicity index and, Fukui indices were also calculated and found well correlated to the reactivity of di-imine-SB.

Dataset Information

A cinnamaldehyde Schiff base of S-(4-methyl-benz-yl) di-thio-carbazate: crystal structure, Hirshfeld surface analysis and computational study.

Publications

A cinnamaldehyde Schiff base of <i>S</i>-(4-methyl-benz-yl) di-thio-carbazate: crystal structure, Hirshfeld surface analysis and computational study.

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