6-Bromo-2-methyl-1<i>H</i>-imidazo[4,5-<i>b</i>]pyridine

Bouayad, K.; Rodi, Youssef Kandri; Ghadraoui, E.H. El; Mague, Joel T.; Essassi, El Mokhtar; Zouihri, Hafid

doi:10.1107/s2414314616007665

Cited by 4 publications

(4 citation statements)

References 7 publications

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“…On the other hand, imidazopyridine compounds, which have a specificity to GPR4 as negative allosteric modulators (Tobo et al, 2015), can also be used for the treatment of gastric and/or duodenal ulcers. Several imidazo[4,5-b]pyridine derivatives have also been ISSN 2056-9890 reported as corrosion inhibitors of steel in an acidic environment (Bouayad et al, 2018;Sikine et al, 2016;Yadav et al, 2014), and also as inhibitors of a nanomolar rhodesaine (Ehmke et al, 2013) or the Et-PKG enzyme (Cheng et al, 2010).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromododecyl)-2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine

Jabri¹,

Jarmoni²,

Hökelek³

et al. 2020

Acta Cryst E

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The title compound, C24H30Br2N4O2, consists of a 2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine entity with a 12-bromododecyl substituent attached to the pyridine N atom. The middle eight-carbon portion of the side chain is planar to within 0.09 (1) Å and makes a dihedral angle of 21.9 (8)° with the mean plane of the imidazolopyridine moiety, giving the molecule a V-shape. In the crystal, the imidazolopyridine units are associated through slipped π–π stacking interactions together with weak C—HPyr...ONtr and C—HBrmdcyl...ONtr (Pyr = pyridine, Ntr = nitro and Brmdcyl = bromododecyl) hydrogen bonds. The 12-bromododecyl chains overlap with each other between the stacks. The terminal –CH2Br group of the side chain shows disorder over two resolved sites in a 0.902 (3):0.098 (3) ratio. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (48.1%), H...Br/Br...H (15.0%) and H...O/O...H (12.8%) interactions. The optimized molecular structure, using density functional theory at the B3LYP/ 6–311 G(d,p) level, is compared with the experimentally determined structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromododecyl)-2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine

Jabri¹,

Jarmoni²,

Hökelek³

et al. 2020

Acta Cryst E

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“…As per the recent report of NACE (National Association of Corrosion Engineers), estimated annual cost of corrosion is close to $100 billion USD [10,11]. For the reason that corrosion causes massive trade and industry and safety losses, numerous preventive methods have been developed from time to time in order to prevent the corrosion and corrosive damages [12][13][14][15]. Out of all used methods, implementation of organic corrosion inhibitors is one of the most significant methods due to its several beneficial properties such as ease of synthesis, ease of application, costeffective and high inhibition performance [16][17][18][19][20].…”

Section: Corrosion and Corrosion Inhibitionmentioning

confidence: 99%

Alkaloids as green and environmental benign corrosion inhibitors: An overview

2019

Int. J. Corros. Scale Inhib.

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Alkaloids are naturally occurring nitrogen containing organic bases that possess diverse and significant physiological effects on animals and humans. They are mostly derived from the plants. Because of their natural and biological origin, they (alkaloids) are considered as environmental benign alternatives to be used as corrosion inhibitors at the place of traditional and toxic synthetic corrosion inhibitors. Numerous alkaloids have been employed as effective corrosion inhibitors for metals and alloys in different electrolytic media. It has been established that alkaloid molecules are associated with extensive conjugation in the form of non-bonding and π-elections through which they can interact strongly and inhibit corrosion efficiently. Present review article features the collection of reports published on the topic alkaloids as corrosion inhibitors. In this review article, we also described the corrosion and its adverse effect, mechanism of corrosion and corrosion inhibition by organic corrosion inhibitors (including alkaloids) and factors affecting the inhibition property of corrosion inhibitors. Literature study suggests that most of the alkaloids are soluble in the polar electrolytic media and thereby behave as good corrosion inhibitors. Present review article describes the inhibition effect of several classes of alkaloids such as pyridine, purine and indole derivatives that have been used previously. Chemical structures alkaloids and their mode of adsorption and interactions with the metallic surface, nature of metal and electrolyte and related salient features have also been tabulated in the review.

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“…The effect of the title compound as an inhibitor of the corrosion of mild steel (MS) were studied using electrochemical impedance spectroscopy in the concentration range of 10 À6 to 10 À3 M at 308 K. The electrochemical experiment consisted of a 3 electrode electrolytic cell consisting of platinum foil as counter-electrode, saturated calomel as reference electrode and MS as working electrode with an exposed area of 1 cm 2 . The MS specimen was immersed in a test solution for 0.5 h until a steady-state potential was achieved using a PGZ100 potentiostat (Bouayad et al, 2018). Electrochemical impedance spectroscopy (EIS) measurements were performed over a frequency range of 0.1 Â 10 À3 KHz to 10 mHz and an amplitude of 10 mV with 10 points per decade.…”

Section: Electrochemical Measurementsmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and corrosion inhibition study of 3,6-bis(pyridin-2-yl)-4-{[(3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-5H-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)methoxy]methyl}pyridazine monohydrate

Filali¹,

Elmsellem²,

Hökelek

et al. 2019

Acta Cryst E

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In the title compound, C27H30N4O6·H2O, the two dioxolo rings are in envelope conformations, while the pyran ring is in a twisted-boat conformation. The pyradizine ring is oriented at dihedral angles of 9.23 (6) and 12.98 (9)° with respect to the pyridine rings, while the dihedral angle between the two pyridine rings is 13.45 (10)°. In the crystal, O—Hwater...Opyran, O—Hwater...Omethoxymethyl and O—Hwater...Npyridazine hydrogen bonds link the molecules into chains along [010]. In addition, weak C—Hdioxolo...Odioxolo hydrogen bonds and a weak C—Hmethoxymethyl...π interaction complete the three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (55.7%), H...C/C...H (14.6%), H...O/O...H (14.5%) and H...N/N...H (9.6%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Electrochemical measurements are also reported.

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6-Bromo-2-methyl-1H-imidazo[4,5-b]pyridine

Cited by 4 publications

References 7 publications

Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromododecyl)-2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine

Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromododecyl)-2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine

Alkaloids as green and environmental benign corrosion inhibitors: An overview

Crystal structure, Hirshfeld surface analysis and corrosion inhibition study of 3,6-bis(pyridin-2-yl)-4-{[(3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-5H-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)methoxy]methyl}pyridazine monohydrate

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