X-ray investigation of glyoxime derivatives. V. Two isomers of 2-(thienyl)glyoxime. A database study of the geometry and hydrogen bonding of the oxime group

Chertanova, L. F.; Pascard, Claudine; Шереметев, А. Б.

doi:10.1107/s0108768194004179

Cited by 45 publications

(38 citation statements)

References 3 publications

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“…It should be noted, however, that this is not the case of the two-positional disorder, since upon dissolution in organic solvents there are two different isomers at room temperature that have different chemical shifts in the 13 C{ 1 H} NMR spectra. This is a fairly rare phenomenon for oximes since both geometrical isomers tend to crystallize separately [51,52]. Nevertheless, cocrystallization of two diastereomers was recently observed for several other mono- and bis-cyanoximes [44,53].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Riddles

Whited

Lotlikar

et al. 2014

Inorganica Chimica Acta

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High-yield syntheses of N-piperidine-cyanacetamide (1), N-morpholyl-cyanacetamide (4) and their oxime derivatives N-piperidine-2-cyano-2-oximino-acetamide (HPiPCO, 2) and N-morpholyc-2-cyano-2-oximino-acetamide (HMCO, 5) were developed using two-step preparations. At first, the reactions of neat cyanoacetic acid esters and the respective cyclic secondary amines such as piperideine and morpholine afforded pure cyanacetamides, which were converted into cyanoximes at room temperature using the nitrosation reaction with gaseous CH3ONO. The synthesized compounds were investigated by means of IR, 1H, 13C and UV-visible spectroscopy. Crystal structures of two starting substituted cyan-acetamides and two target cyanoximes were determined. Silver(I) complexes of AgL composition (L = PipCO, 3; MCO, 6) were prepared in high yield. Both metal complexes are thermally stable above 100oC, and remarkably stable to high intensity visible light. The stability of dried AgL compounds towards short wavelength UV-radiation (a frequently used germicidal light) was examined using diffusion reflectance spectroscopy. Both complexes demonstrate slow photoreduction within ~3 hrs, observable as a gradual color change and darkening due to the formation of fine (nano-scale) particles of metallic silver. The complex Ag(MCO), 6, is about 2.6 times less stable towards UV-radiation than its more lypophyllic analog Ag(PipCO), 3. Antimicrobial and biofilm growth inhibition properties of the prepared solid acrylate-based polymeric composites containing embedded silver(I) cyanoximates were investigated using three human pathogens: P. aeruginosa PAO1 (wound isolate), S. aureus NRS70 (methicillin resistant respiratory isolate), and S. mutans UA159 (cariogenic dental isolate). Studies showed that both 3 and 6 compounds completely abolished the growth of PAO1 at 0.5 weight % concentration, and the growth of UA159 and NRS70 at 1% concentration. Moreover, data demonstrates that complexes 3 and 6 also inhibit both planktonic and biofilm growth of Gram-positive and Gram-negative bacterial pathogens. The demonstrated thermal stability and pronounced antimicrobial activity of both silver(I) cyanoximates indicates the strong potential for the studied complexes to be used as light insensitive antimicrobial additives to light-curable adhesives that set indwelling devices in place.

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Riddles

Whited

Lotlikar

et al. 2014

Inorganica Chimica Acta

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“…This fact was noticed by Chertanova and Pascard [22]. Even though in 3 such an intramolecular hydrogen bond should, in principle, be possible in view of the vicinity of the oxime and carboxylic functions The molecular geometries of both compounds are quite typical, with very sharp intraannular bond an gles (see Table 5).…”

Section: Resultsmentioning

confidence: 83%

Hydrogen Bonds in "Carboxyoximes": the Case of Bomane Derivatives

Kubicki¹,

Borowiak²,

Antkowiak³

2000

Zeitschrift Für Naturforschung B

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The tendency of forming mixed carboxyl-to-oxime hydrogen bonds was tested on the series of bomane derivatives: one with the acid function only (bomane-2-erajfo-carboxylic acid), one with the oxime function (2,2'-diethylthiobomane-3-oxime), and one with both oxime and carboxylic functions (bomane-2-oxime-3-endo-carboxylic acid). The crystal structures of these compounds were determined by means of X-ray diffraction. In bomane-2-^n^/o-carboxylic acid and 2,2'-diethylthiobom ane-3-oxime 'homogenic' hydrogen bonds were found, and these hydrogen bonds close eight-and six-membered rings, respectively. By contrast, in bomane-2-oxime-3-era/o-carboxylic acid 'heterogenic' hydrogen bonds between carboxylic and oxime bonds were found. This carboxylic-oxime, or 'carboxyoxime' system is almost always present in compounds which have both oxime and carboxylic groups; therefore it can be regarded as an element of supramolecular structures (synthon). The presence of such synthons can break the tendency of carboxylic acids and oximes towards crystallizing in centrosymmetric structures.

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“…The glyoxime group showed E,Zconfiguration. 4 In this configuration, one oxime group, C7=N2-O1-H1O1, participated as a donor in an O1-H1O1···O2 intermolecular hydrogen bond. The detailed values were: O1···O2(i) 2.835(2)Å, O1-H1O1···O2(i) 174(3)˚ [symmetry codes: (i) x, y, z−1].…”

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confidence: 99%