Cellulose organic solvents. III. The structure of the N-methylmorpholine N-oxide–trans-1,2-cyclohexanediol complex

Chanzy, H.; Maia, Elaine Rose; Pérez, S.

doi:10.1107/s0567740882004221

Cited by 23 publications

(14 citation statements)

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“…The use of 4 Å molecular sieves is essential to remove the water introduced from wet NMO·H 2 O, and water generated during the reaction. [43] The role of water as a hydrogen-bond donor was explored by 1 H NMR spectroscopy. N-Oxides are ubiq- Figure 3.…”

Section: Resultsmentioning

confidence: 99%

“…[38][39][40] Crystal structures reveal that the O --atom of NMO H-bonds to waters of hydration in the solid state (NMO·H 2 O [41] and NMO·2.5H 2 O [42] ) as well as the hydroxyl protons of alcohols such as 1,2-cyclohexandiol in cocrystals. [43] The role of water as a hydrogen-bond donor was explored by 1 H NMR spectroscopy. The 1 H NMR spectra of NMO and 1-octanol in d 3 -acetonitrile are presented in Figure 3.…”

Section: Resultsmentioning

confidence: 99%

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Hydrogen‐Bonding Interactions in the Ley–Griffith Oxidation: Practical Considerations for the Synthetic Chemist

et al. 2018

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The Ley–Griffith oxidation, which is catalyzed by tetra‐n‐propylammonium perruthenate (TPAP, nPr4N[RuO4]), is a popular method for not only controlled oxidation of primary alcohols to aldehydes, but also a host of other synthetically useful transformations. While the fundamental reaction mechanism has recently been elucidated, several key hydrogen‐bonding interactions between the reagents were implicated but not investigated. Herein the prevalence of H‐bonding between the co‐oxidant N‐methylmorpholine N‐oxide (NMO), the alcohol substrate, water and the perruthenate catalyst is established. These observations help to rationalize the importance of drying the reagents and lead to several practical suggestions.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Hydrogen‐Bonding Interactions in the Ley–Griffith Oxidation: Practical Considerations for the Synthetic Chemist

et al. 2018

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“…The final goal is to prepare regenerated cellulose films and fibers through a simple and non-polluting process. N-methyl morpholine N-oxide (NMMO) appears to be the most potential direct solvent for cellulose because it is environmentally friendly and easily recycled [5][6][7][8][9][10][11]. In 1999, Freddi [12] first found that NMMO monohydrate was also a good direct solvent for SF, and its relatively low melting point allows people to conduct dissolution and spinning experiments in a reasonably safe temperature range (90-110 • C) without excessive thermal degradation of the SF.…”

Section: Introductionmentioning

confidence: 98%

Solubility and rheological behavior of silk fibroin (Bombyx mori) in N-methyl morpholine N-oxide

Zhang

Shao

et al. 2005

International Journal of Biological Macromolecules

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“…In many instances (4)(5)(6), amine N-oxides crystallized from aqueous alcoholic solutions or water are in the form of hydrates. However, a systematic structural study of this class of hydrated compounds has rarely been attempted.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural characterization of N,N′-diarylpiperazine N,N′-dioxide tetrahydrates (aryl = o-tolyl, p-tolyl, p-chlorophenyl)

Kwok¹,

Mak²

1988

Can. J. Chem.

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The synthesis and X-ray structure determination of N,N′-di(o-tolyl)piperazine N,N′-dioxide tetrahydrate, I, N,N′-di(p-tolyl)piperazine N,N′-dioxide tetrahydrate, II, and N,N′-di(p-chlorophenyl)piperazine N,N′-dioxide tetrahydrate, III, are described. Compound I crystallizes in space group [Formula: see text] with a = 7.778(1), b = 7.915(2), c = 8.919(2) Å, α = 106.25(2), β = 99.56(1), γ = 108.80(2)°, and Z = 1. Compound II crystallizes in space group [Formula: see text] with a = 6.558(1), b = 7.134(2), c = 11.610(3) Å; α = 73.23(2), β = 78.08(2), γ = 72.67(2)°, and Z = 1. Compound III crystallizes in space group P21/c with a = 9.159(3), b = 12.390(4), c = 8.339(4) Å, β = 97.38(3)°, and Z = 2. The structures of I–III were solved by the direct method and refined to R = 0.049 (1749 observed MoKα reflections), 0.055 (2651 observed reflections), and 0.035 (1827 observed reflections), respectively. In each case, the N,N′-dioxide molecule occupies a site of symmetry [Formula: see text]. The piperazine ring takes the chair form, with two N—O bonds oriented axially in a trans configuration. The structures are characterized by strong hydrogen bonding between the water molecules, as well as between the N-oxide groups and water molecules, giving rise to puckered layers composed of various combinations of edge-sharing four-membered, six-membered, ten-membered, and twelve-membered rings. The aryl rings, which protrude on both sides of each puckered layer, constitute hydrophobic regions separating the hydrophilic layers in the crystal packing.

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Cellulose organic solvents. III. The structure of the N-methylmorpholine N-oxide–trans-1,2-cyclohexanediol complex

Cited by 23 publications

References 0 publications

Hydrogen‐Bonding Interactions in the Ley–Griffith Oxidation: Practical Considerations for the Synthetic Chemist

Hydrogen‐Bonding Interactions in the Ley–Griffith Oxidation: Practical Considerations for the Synthetic Chemist

Solubility and rheological behavior of silk fibroin (Bombyx mori) in N-methyl morpholine N-oxide

Synthesis and structural characterization of N,N′-diarylpiperazine N,N′-dioxide tetrahydrates (aryl = o-tolyl, p-tolyl, p-chlorophenyl)

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