Crystal Structures of 1-Hydroxyimidazole and Its Salts

Laus, Gerhard; Kahlenberg, Volker

doi:10.3390/cryst2041492

Cited by 7 publications

(4 citation statements)

References 18 publications

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“…The structure was solved by direct methods and refined in anisotropic approximation using Olex2 software. 21 Positions of hydrogen atoms were calculated geometrically with the exception of the OH group hydrogen atoms that were determined objectively. The hydrogen atoms were refined using "riding" model.…”

Section: X-ray Determinationmentioning

confidence: 99%

“…18 Unambiguous evidence for the occurence of the Nhydroxyimidazole tautomeric form in the solid state may be obtained from the X-ray structural analysis data (see, e.g., papers). [19][20][21][22][23][24][25] In the report 24 the X-ray data for 1-hydroxyimidazole derivatives were considered with regard to their tautomeric form stabilization.…”

Section: Synthesis and Study Of Prototropicmentioning

confidence: 99%

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Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

et al. 2015

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Please cite this article as: Nikitina PA, Peregudov AS, Koldaeva TY, Kuz'mina LG, Adiulin EI, Tkach II, Perevalov VP, Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles, Tetrahedron (2015), Novel 2-(2-hydroxyphenyl) substituted imidazoles have been synthesized. A prototropic tautomerism of the 1-hydroxyimidazole derivatives has been studied. X-ray diffraction analysis and IR-spectroscopy have revealed that in the solid state the title compounds exist as the Nhydroxy tautomers. The 1 H and 13 C NMR spectra of the new imidazole derivatives are discussed. It has been shown that in chloroform solutions 5-carbonylsubstituted 2-(2-hydroxyphenyl)-1-hydroxyimidazoles exist in the N-hydroxy tautomeric form. A transition to DMSO results in the existence of the 1-hydroxyimidazoles under study as the N-oxide tautomers.

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Section: X-ray Determinationmentioning

confidence: 99%

Section: Synthesis and Study Of Prototropicmentioning

confidence: 99%

Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

et al. 2015

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“…Chromenyl derivatives used in the Nikitina et al study [16], 4 and 5 in Table 1, were reported to exist in the Noxide form in the solid state. In addition, the crystal structures of protic salts of 1-hydroxyimidazole, [17], and some Cu and Zn complexes of imidazole N-oxide derivatives have been reported [20].…”

Section: Introductionmentioning

confidence: 98%

“…These include for 1-hydroxyimidazole compounds, the parent compound, 1-hydroxyimidazole, 1 [17], and the 2,4,5-trisubstituted derivatives, 1-hydroxy-2-phenyl-4-methyl-5-benzylimino-(4-N,N-dimethylaminophenyl)methylidinoimidazole monohydrate, 2 [18], N-H-O (CO of chromene) chains and 2-benzoyl-1-hydroxy-4,5-dimethylimidazole, 3 [19]. Chromenyl derivatives used in the Nikitina et al study [16], 4 and 5 in Table 1, were reported to exist in the Noxide form in the solid state.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures of 1-hydroxylimidazole and imidazole 1-oxide derivatives

Silva¹,

Silva²,

Carvalho³

et al. 2014

Zeitschrift Für Kristallographie - Crystalline Materials

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The N-oxide or 1-hydroxy forms of four solid 1-hydroxy-5-(4-methyl-2-nitroimidazol-2-yl)-4-phenyl-2-(Xphenyl)-imidazole derivatives, 6, have been studied by X-ray crystallography. Compounds, (6: X = 4-Br) and (6: X = 2-O 2 N), both recrystallized from EtOH, and (6: X = 4-F), recrystallized from EtOCH 2 CH 2 OH, were isolated in the 1-hydroxyimidazole form. In contrast, (6: X = H), recrystallized from EtOCH-2 CH 2 OH, was obtained in the imidazole N-oxide form. Two independent molecules, Mol A and Mol B, rotamers, are present in the asymmetric unit of the imidazole N-oxide compound, (6: X = H) and are linked into chains of alternating compounds, mainly by N-H···O hydrogen bonds, but also by N-H···N and C-H···O hydrogen bonds and π···π interactions. These chains are linked by other C-H···O and C-H···N hydrogen bonds and π···π interactions into a 3-D arrangement. In the 1-hydroxyimidazole compound, (6: X = 2-O 2 N), classical hydrogen bonds, O1-H1···N3, are the major interactions linking molecules into C(5) chains: weak π···π stacking interactions also link the molecules within the chains. These chains are linked by C-H···O and hydrogen bonds and by N-O···π interactions into a three-dimensional array. The other 1-hydroxyimidazole compounds, (6: X = 4-Br) and(6: X = 4-F), have similar structures, which differ from that of (6: X = 2-O 2 N). In (6: X = 4-Br) and (6: X = 4-F), pairs of classical O-H···N hydrogen bonds link molecules into symmetric dimers: these dimers are further stabilized by π···π interactions. Other intermolecular interactions found in both (6: X = 4-Br) and (6: X = 4-F) are C-H···O hydrogen bond and N-O···π interactions, which link the O-H···N hydrogen bonded dimers into a 3-dimensional array.

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Crystallography of Ionic Liquids

Winterton

2015

Ionic Liquids Completely UnCOILed

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Crystal Structures of 1-Hydroxyimidazole and Its Salts

Cited by 7 publications

References 18 publications

Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

Crystal structures of 1-hydroxylimidazole and imidazole 1-oxide derivatives

Crystallography of Ionic Liquids

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