Crystal structure of 3,5-dimethylpyridineN-oxide dihydrate

García, Rosario Merino; Ríos-Merino, Francisco Javier; Bernès, Syl­vain; Reyes‐Ortega, Yasmi

doi:10.1107/s205698901601687x

Cited by 2 publications

(1 citation statement)

References 23 publications

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“…Probably the most frequent use of such compounds is in various oxidation reactions where they act as oxidants 4 . Pyridine N-oxides and many of their ring-functionalized derivatives are recurrent molecules of biologically active and pharmacological agents 5 , and a clear spatial distribution by different spectroscopic tools has been established for some of them 6,7 . In research on attaching different groups to the pyridine ring, scientists have tested various methodologies to produce an easy and conventional method, since isoxazolines requires a catalytic amount of base such as DBU in boiling xylene to form 6substituted-2-aminopyridine N-oxides 8,9 .…”

Section: Introductionmentioning

confidence: 99%

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Merino-García

Hernández-Anzaldo

Reyes‐Ortega

2018

JoVE

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The synthesis of 3,5-lutidine N-oxide dehydrate, 1, was achieved in the synthesis route of 2-amino-pyridine-3,5-dicarboxylic acid. Ochiai first used the methodology for non-substituted pyridines in 1957 in a 12 h process, but no X-ray suitable crystals were obtained. The substituted ring used in the methodology presented here clearly influenced the addition of water molecules into the asymmetric unit, which confers a different nucleophilic strength in 1. The X-ray suitable crystal compound 1 was possible due to the stabilization of the negative charge in the oxygen by the presence of two water molecules where the hydrogen atoms donate positive charge into the ring; such water molecules serve well to construct a supramolecular interaction. The hydrated molecules may be possible for the alkaline system that is reached by adjusting the pH to 10. Importantly, the double methyl substituted ring and a reaction time of 5 h, makes it a more versatile method and with wider chemical applications for future ring insertions.

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Section: Introductionmentioning

confidence: 99%

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Merino-García

Hernández-Anzaldo

Reyes‐Ortega

2018

JoVE

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From Hydrate to Peroxosolvate: A Test of Prediction with Cyclic N-Oxides

Foroughi

Matzger

2021

Crystal Growth & Design

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Peroxosolvate formation is a promising method for developing energetic materials with improved properties (e.g., oxygen balance and overall performance); however, one challenge that remains is the prediction of compounds that are likely to form peroxosolvates. Hydrogen bond donation in hydrate structures was exploited to identify possible hydrogen peroxide solvate formers in the Cambridge Structural Database, leading to the discovery of a peroxosolvate crystal form for each of the six N-oxide compounds that met the search criteria. The resulting peroxosolvates were characterized by single-crystal X-ray diffraction and Raman spectroscopy, and the crystal structures were compared with the corresponding hydrate structures to identify trends in hydrogen bond donation, demonstrating that, in the developed peroxosolvates, the O−H•••O−N interaction is stronger in the peroxosolvate than in the hydrate. The success of this peroxosolvate discovery strategy for N-oxide-containing compounds provides insight into how to identify target molecules that may form peroxosolvates; this study will affect energetic materials in particular, where the compounds can be dangerous to handle and/or difficult to synthesize.

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Crystal structure of 3,5-dimethylpyridineN-oxide dihydrate

Abstract: In the title hydrate, water molecules and N-oxide groups of the main molecule form supramolecular chains based on R(10) ring motifs.

Cited by 2 publications

References 23 publications

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine <em>N</em>-Oxide Dehydrate

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine <em>N</em>-Oxide Dehydrate

From Hydrate to Peroxosolvate: A Test of Prediction with Cyclic N-Oxides

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Crystal structure of 3,5-dimethylpyridineN-oxide dihydrate

Abstract: In the title hydrate, water mol­ecules and N-oxide groups of the main mol­ecule form supra­molecular chains based on R(10) ring motifs.

Cited by 2 publications

References 23 publications

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine <em>N</em>-Oxide Dehydrate

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine <em>N</em>-Oxide Dehydrate

From Hydrate to Peroxosolvate: A Test of Prediction with Cyclic N-Oxides

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Abstract: In the title hydrate, water molecules and N-oxide groups of the main molecule form supramolecular chains based on R(10) ring motifs.