Thymine hydrogen peroxide 0.55-solvate 0.45-hydrate

Churakov, Andrei V.; Howard, Judith A. K.

doi:10.1107/s1600536807053585

Cited by 17 publications

(14 citation statements)

References 6 publications

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“…[11] Thus as eries of theoretical studies on H 2 O 2 and H 2 O 2 -water clusters was recently performed. [12][13][14][15][16] Surprisingly,t he experimental X-ray data on such clusters are very sparse.Despite the particular attention attracted to structures of hydrogen-bonded complexes of H 2 O 2 , [17][18][19][20] only structures containing low-order D3 peroxide clusters [20] and C1 peroxide and peroxide-water chains have been reported to date [21,22] (D3 and C1 are Infantes-Motherwell notion [23] ). In contrast, hundreds of large water clusters are known, [23] especially in protein cavities.…”

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confidence: 99%

“…Only the structures containing low-order D3 peroxide cluster (H 2 O 2 ) 3 [18] and infinite C1 peroxide or peroxide-water chains have been reported to date. [20][21][22] The(H 2 O 2 ) 12 cluster is described in Scheme 1a.…”

mentioning

confidence: 99%

“…Theonly known to date infinite C1 chain in the structure of thymine peroxosolvate belongs to the "hydroperoxo" type. [20,21] Thehydroperoxo-anionic chains in the structure of ammonia peroxosolvate NH 4 + OOH À are also organized in "head-to-tail" manner. [28] However,b oth terminal D5 chains in I represent mixed "hydroperoxo-hydroxo" linkages.…”

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confidence: 99%

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Hydrogen Peroxide Insular Dodecameric and Pentameric Clusters in Peroxosolvate Structures

Grishanov¹,

Navasardyan²,

Medvedev³

et al. 2017

Angew Chem Int Ed

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Peroxosolvates of 2-aminonicotinic acid (I) and lidocaine N-oxide (II) including the largest insular hydrogen peroxide clusters were isolated and their crystal structures were determined by single-crystal X-ray diffraction. An unprecedented dodecameric hydrogen peroxide insular cluster was found in I. An unusual cross-like pentameric cluster was observed in the structure of II. The topology of the (H O ) assembly was never observed for small-molecule clusters. In I and II new double and triple cross-orientational disorders of H O were found. Cluster II is the first example of a peroxosolvate crystal structure containing H O molecules with a homoleptic hydrogen peroxide environment. In II, a hydrogen bond between an H O molecule and a peptide group -CONH⋅⋅⋅O H was observed for the first time.

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Hydrogen Peroxide Insular Dodecameric and Pentameric Clusters in Peroxosolvate Structures

Grishanov¹,

Navasardyan²,

Medvedev³

et al. 2017

Angew Chem Int Ed

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“…GOOF = 1.029, Δρ min/max = -0.168/0.326. In the structure no partial substitutional disorder of hydrogen peroxide by water molecules [13][14][15][16] was observed since no residual peaks with intensity more than 0.15 e/Å 3 were seen within 0.8 Å from the centers of O-O bonds. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no.…”

Section: Methodsmentioning

confidence: 87%

“…It should be noted that all distances between peroxide oxygen atoms and ammonium hydrogen atoms are greater than 2.55 Å and thus could not be considered as acceptor H-bonds. We have shown for a wide range of compounds that two donor hydrogen bonds were the minimal number of interactions for organic peroxosolvates [12][13][14][15][16]. Thus, only two H-bonds formed by peroxide molecules were observed in the structures of Ph 4 X + Hal -·2(H 2 O 2 ) (X = P, As; Hal = Cl, Br) [6] and phosphine oxide peroxosolvates [17,18], wherein the peroxide hydrogen atoms were the only active hydrogen atoms.…”

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confidence: 84%

Crystal structure of ammonium succinate peroxosolvate

et al. 2014

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The crystal structure of previously unknown ammonium succinate peroxosolvate is studied. It is shown that it represents a rare example of the structure where H 2 O 2 molecule forms two donor hydrogen bonds and does participate in any acceptor hydrogen bonds, despite the presence of substantial quantity of nonperoxide active hydrogen atoms.Peroxosolvates are molecular adducts of hydrogen peroxide with various inorganic and organic compounds. Several of them are widely used in industry, household chemistry and medicine as solid and stable enough sources of hydrogen peroxide in bleaching and disinfection processes. Annual world production of Na 2 CO 3 ·1.5H 2 O 2 and urea peroxosolvates CH 4 N 2 O · H 2 O 2 has risen to hundreds of thousands tons [1].For the first time peroxosolvates of organic compounds were obtained by S. Tanatar in 1908 [2]. He synthesized and established the composition of urea peroxosolvate. That compound immediately attracted great attention both from theoretical and practical points of view. Its crystal structure was completely determined by X-ray diffraction as early as in 1941 [3]. Until quite recently, urea peroxosolvate remains the target of intensive research [4][5][6]. In [2], another peroxosolvate of a simple organic compound was obtained, namely peroxosolvate of succinimide. It was crystallized by slow evaporation of the solution of succinimide in 30% Н 2 О 2 at 50°С. The composition (C 4 H 5 NO 2 ·H 2 O 2 ) was established by permanganatometric titration of the included peroxide [2]. Surprisingly, we did not find any mentions about this compound in the later literature. We made systematic attempts to crystallize this compound from saturated (at r.t.) solutions of succinimide in hydrogen peroxide of various concentrations (30%, 50%, 70% and 96%) by cooling down to +5 °C, -12 °C and -18 °С. However, in all trials the resulting crystals were nothing else but the starting succinimide, as it was shown by X-ray diffraction.It is known that cyclic imides undergo hydrolytic degradation in acidic media resulting in a range of products [7]: Scheme 1.

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Hydrogen Peroxide Insular Dodecameric and Pentameric Clusters in Peroxosolvate Structures

Grishanov¹,

Navasardyan²,

Medvedev³

et al. 2017

Angewandte Chemie

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Peroxosolvates of 2-aminonicotinic acid (I)a nd lidocaine N-oxide( II)i ncluding the largest insular hydrogen peroxideclusters were isolated and their crystal structures were determined by single-crystal X-ray diffraction. An unprecedented dodecameric hydrogen peroxide insular cluster was found in I.A nu nusual cross-like pentameric cluster was observed in the structure of II.T he topology of the (H 2 O 2 ) 12 assembly was never observed for small-molecule clusters.InI and II new double and triple cross-orientational disorders of H 2 O 2 were found. Cluster II is the first example of ap eroxosolvate crystal structure containing H 2 O 2 molecules with ahomoleptic hydrogen peroxide environment. In II,ahydrogen bond between an H 2 O 2 molecule and ap eptide group -CONH···O 2 H 2 was observed for the first time.

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Thymine hydrogen peroxide 0.55-solvate 0.45-hydrate

Cited by 17 publications

References 6 publications

Hydrogen Peroxide Insular Dodecameric and Pentameric Clusters in Peroxosolvate Structures

Hydrogen Peroxide Insular Dodecameric and Pentameric Clusters in Peroxosolvate Structures

Crystal structure of ammonium succinate peroxosolvate

Hydrogen Peroxide Insular Dodecameric and Pentameric Clusters in Peroxosolvate Structures

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