Non-covalent interactions of N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives—a case of intramolecular N-oxide hydrogen bonds

Łukomska-Rogala, Marlena; Rybarczyk‐Pirek, Agnieszka J.; Ejsmont, Krzysztof; Jasiński, Marcin; Palusiak, Marcin

doi:10.1007/s11224-017-0935-x

Cited by 10 publications

(10 citation statements)

References 35 publications

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“…Due to the disorder in the structure of (II), no similar conclusions can be drawn. For more information on weak interactions with contributions of the N-oxide group, see recent work from our group (Wzgarda-Raj et al, 2018, 2021Rybarczyk-Pirek et al, 2014, 2015Łukomska-Rogala et al, 2017), including a comparison of N-oxide and other oxygen-containing groups (Łukomska et al, 2015). Scheme of the hydrogen-bonding synthon of the sulfonamide group in the crystal structures of (I) and (II), showing the interaction motif symbols (R is a ring and D is a dimer) proposed by Etter (1990).…”

Section: Figurementioning

confidence: 99%

A novel hydrogen-bondingN-oxide–sulfonamide–nitro N—H...O synthon determining the architecture of benzenesulfonamide cocrystals

Wzgarda-Raj¹,

Rybarczyk‐Pirek²,

Wojtulewski³

et al. 2022

Acta Crystallogr C

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The structures of novel cocrystals of 4-nitropyridine N-oxide with benzenesulfonamide derivatives, namely, 4-nitrobenzenesulfonamide–4-nitropyridine N-oxide (1/1), C5H4N2O3·C6H6N2O4S, and 4-chlorobenzenesulfonamide–4-nitropyridine N-oxide (1/1), C6H6ClNO2S·C5H4N2O3, are stabilized by N—H...O hydrogen bonds, with the sulfonamide group acting as a proton donor. The O atoms of the N-oxide and nitro groups are acceptors in these interactions. The latter is a double acceptor of bifurcated hydrogen bonds. Previous studies on similar crystal structures indicated competition between these functional groups in the formation of hydrogen bonds, with the priority being for the N-oxide group. In contrast, the present X-ray studies indicate the existence of a hydrogen-bonding synthon including N—H...O(N-oxide) and N—H...O(nitro) bridges. We present here a more detailed analysis of the N-oxide–sulfonamide–nitro N—H...O ternary complex with quantum theory computations and the Quantum Theory of Atoms in Molecules (QTAIM) approach. Both interactions are present in the crystals, but the O atom of the N-oxide group is found to be a more effective proton acceptor in hydrogen bonds, with an interaction energy about twice that of the nitro-group O atoms.

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Section: Figurementioning

confidence: 99%

A novel hydrogen-bondingN-oxide–sulfonamide–nitro N—H...O synthon determining the architecture of benzenesulfonamide cocrystals

Wzgarda-Raj¹,

Rybarczyk‐Pirek²,

Wojtulewski³

et al. 2022

Acta Crystallogr C

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“…The results of mapping onto the molecular Hirshfeld surfaces are presented in this paper according to the standard red-white-blue coloring scheme: white color corresponds to intermolecular contacts of length close to the van der Waals separations, red-denotes shorter contacts of negative values of d norm , and blue corresponds to long contacts characterized by positive values of d norm . This relatively new method was effectively used to describe intermolecular interactions in various types of crystals [78][79][80][81].…”

Section: Molecular Hirshfeld Surface Analysismentioning

confidence: 99%

Simple Trans-Platinum Complex Bearing 3-Aminoflavone Ligand Could Be a Useful Drug: Structure-Activity Relationship of Platinum Complex in Comparison with Cisplatin

Fabijańska

Orzechowska

Rybarczyk‐Pirek

et al. 2020

IJMS

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Following previous studies devoted to trans-Pt(3-af) 2 Cl 2 , in this paper, the molecular structure and intermolecular interactions of the title complex are compared with other cisplatin analogues of which the crystal structures are presented in the Cambridge Structural Database (CSD). Molecular Hirshfeld surface analysis and computational methods were used to examine a possible relationship between the structure and anticancer activity of trans-Pt(3-af) 2 Cl 2 . The purpose of the article was also to investigate the effect of hyperthermia on the anticancer activity of cisplatin, cytostatics used in the treatment of patients with ovarian cancer and a new analogue of cisplatin-trans-Pt(3-af) 2 Cl 2 . The study was conducted on two cell lines of ovarian cancer sensitive to Caov-3 cytostatics and the OVCAR-3 resistant cisplatin line. The study used the MTT (3-(4,5-dimethylthiazol-2,5-diphenyltetrazolium bromide) cell viability assay, LDH (lactate dehydrogenase), and the quantitative evaluation method for measuring gene expression, i.e., qPCR with TagMan probes. Reduced survivability of OVCAR-3 and Caov-3 cells exposed to cytostatics at elevated temperatures (37 • C, 40 • C, 43 • C) was observed. Hyperthermia may increase the sensitivity of cells to platinum-based antineoplastic drugs and paclitaxel, which may be associated with the reduction of gene expression related to apoptotic processes.

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“…The X-ray studies of the title compound are a part of our ongoing studies on synthesis and analysis of novel pyridine N-oxides cocrystals [11][12][13][14]. As an object of our work, we have chosen 1-mercaptopyridine N-oxide-a compound of confirmed bioactivity for which two tautomeric forms have been reported [15].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of 2-mercaptopyridine N-oxide upon iodine agent: structural and FT-IR studies on charge-assisted hydrogen bonds CAHB(+) and I…I halogen interactions in 2,2′-dithiobis(pyridine N-oxide) ionic cocrystal

et al. 2019

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2-Mercaptopyridine N-oxide (I) undergoes spontaneous dimerization to the disulfide form due to reaction with iodine acting as an oxidizing reagent. As a result, a di-N-oxide disulfide derivative of pyridine is obtained. During the process of crystallization, one of N-oxide groups undergoes protonation and a cation form of disulfide moiety cocrystallizes with I 3 − counterion forming a salt structure. Therefore, in the crystalline state, the 2,2′-dithiobis(pyridine N-oxide) molecule exists in a not observed previously form of monocation. Interestingly, the protonated N-oxide group does not form hydrogen-bonded salt bridges (of the CAHB(±) type with I 3 − anions) but prefers to be involved in intermolecular interactions with the unprotonated N-oxide group of the adjacent molecule This results in formation of intermolecular CAHB(+) hydrogen bridges finally linking molecules into infinite chains. The crystal structure is also stabilized by other various noncovalent interactions, including iodine...iodine and sulfur...iodine contacts.

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Non-covalent interactions of N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives—a case of intramolecular N-oxide hydrogen bonds

Cited by 10 publications

References 35 publications

A novel hydrogen-bondingN-oxide–sulfonamide–nitro N—H...O synthon determining the architecture of benzenesulfonamide cocrystals

A novel hydrogen-bondingN-oxide–sulfonamide–nitro N—H...O synthon determining the architecture of benzenesulfonamide cocrystals

Simple Trans-Platinum Complex Bearing 3-Aminoflavone Ligand Could Be a Useful Drug: Structure-Activity Relationship of Platinum Complex in Comparison with Cisplatin

Oxidation of 2-mercaptopyridine N-oxide upon iodine agent: structural and FT-IR studies on charge-assisted hydrogen bonds CAHB(+) and I…I halogen interactions in 2,2′-dithiobis(pyridine N-oxide) ionic cocrystal

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