Combination of DOSY and 1D selective gradient TOCSY: Versatile NMR tools for identify the mixtures from glycerol hydrogenolysis reaction

Lyu, Zexiang; Yue, Fen; Yan, Xiuyin; Shan, Jianfeng; Xiang, Danlei; Pedersen, Christian; Li, Chunju; Wang, Yingxiong; Qiao, Yan

doi:10.1016/j.fuproc.2017.11.011

Cited by 8 publications

(8 citation statements)

References 38 publications

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“…In the 1D version, a single resonance is selectively irradiated, and then, through the 1 H coupling network, the magnetization is propagated, resulting in the selective and clean visualization of the whole spin network . Namely, by selectively exciting a known signal, a subspectrum of the molecule from a complicated spectrum with severely overlapped signals can be extracted. , Therefore, the peaks of the 1 H spectrum at 2.04, 2.39, and 4.24 ppm were selectively excited, and their corresponding subspectra are shown in Figure . According to these Sel-TOCSY spectra, the signals of [Pro] − and both the α- and β-GlcNH 2 tautomers were clearly distinguished.…”

Section: Resultsmentioning

confidence: 99%

“…40 Namely, by selectively exciting a known signal, a subspectrum of the molecule from a complicated spectrum with severely overlapped signals can be extracted. 41,42 Therefore, the peaks of the 1 H spectrum at 2.04, 2.39, and 4.24 ppm were selectively excited, and their corresponding subspectra are shown in Figure 2. According to these Sel-TOCSY spectra, the signals of [Pro] − and both the αand β-GlcNH 2 tautomers were clearly distinguished.…”

Section: Catalytic Interaction Between [Ch][pro] and Glcnhmentioning

confidence: 99%

See 1 more Smart Citation

Amino Acid Ionic Liquids Catalyzed d-Glucosamine into Pyrazine Derivatives: Insight from NMR Spectroscopy

Liu

Zhang

Qiao

et al. 2021

J. Agric. Food Chem.

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Using environment-friendly catalysts to convert biomass into compounds with high values is one of the central topics of green chemistry. In this work, [Ch][Pro] (cholinium as the cation and L-proline as the anion) ionic liquid was synthesized and applied as a model catalyst in the production of deoxyfructosazine (DOF) and fructosazine (FZ) from D-glucosamine (GlcNH 2 ). The 13 C NMR chemical shift titration experiments and the diffusion-ordered NMR spectroscopy (DOSY) measurements showed that, when the [Ch][Pro] interacted with GlcNH 2 , the L-proline anion ([Pro] − ) played a major catalytic role instead of cholinium cation ([Ch] + ). The effects of the reaction temperature and the amount of [Ch][Pro] on the product yields were surveyed. The experimental results showed that the highest DOF yield (33.78%) was obtained after 30 min at 100 °C when the molar ratio of [Ch][Pro]/GlcNH 2 was 1. Moreover, in situ 1 H NMR and in situ 13 C NMR experiments were applied to monitor the reaction process with [Ch][Pro] as the catalyst. The reactive intermediate, dihydrofructosazine, was clearly detected by these in situ techniques. Accordingly, a possible reaction pathway was proposed. By applying other amino acids as the anions, we also prepared five other [Ch][AA] ionic liquids, and they showed different catalytic activities and selectivity in the GlcNH 2 self-condensation reaction.

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Section: Resultsmentioning

confidence: 99%

Section: Catalytic Interaction Between [Ch][pro] and Glcnhmentioning

confidence: 99%

Amino Acid Ionic Liquids Catalyzed d-Glucosamine into Pyrazine Derivatives: Insight from NMR Spectroscopy

Liu

Zhang

Qiao

et al. 2021

J. Agric. Food Chem.

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“…Selective variants of numerous NMR experiments have been realized since the idea of converting multi-dimensional to 1D experiments using selective pulses was reported (Kessler et al (1986)). Such experiments are often exploited to simplify 2014)), to focus the diffusion experiment onto select molecules in a complex mixture (Lyu et al (2018)), or to use the diffusion dimension as an access point to further selective-based NMR experiments (e.g.…”

Section: Resultsmentioning

confidence: 99%

“…selective TOCSY (Lyu et al (2018)) and supplemented with relaxation encoding (Poggetto et al (2017))).…”

Section: Resultsmentioning

confidence: 99%

Selective excitation enables encoding and measurement of multiple diffusion parameters in a single experiment

MacKinnon¹,

Jouzdani²,

Glöge³

et al. 2021

Preprint

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Abstract. Band selectivity to address specific resonances in a spectrum enables one to encode individual settings for diffusion experiments. In a single experiment, this could include different gradient strengths (enabling coverage of a larger range of diffusion constants), different diffusion delays, or different gradient directions (enabling anisotropic diffusion measurement). In this report a selective variant of the bipolar pulsed gradient, eddy-current delay (BPP-LED) experiment enabling selective encoding of three resonances was implemented. As proof-of-principle, the diffusion encoding gradient amplitude was assigned a range dependent on the selected signal, thereby allowing the extraction of the diffusion coefficient for water and a tripeptide (Met-Ala-Ser) with optimal settings in a single experiment.

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“…To solve these issues, matrix-assisted DOSY has developed. In this method, chromatographic supports, surfactants, polymers, or other matrices are added, and the resolution of signals in the diffusion dimension can thereby be improved dramatically. − As reported in our studies, 1D selective gradient total correlation spectroscopy (TOCSY) is also found to be a powerful method, which complements the DOSY technique . A subspectrum of the components in the mixture can be extracted from the spectrum of the highly complex mixture if the mixing time (a key parameter in 1D selective gradient TOCSY experiment) is suitable to transfer the magnetization to all nuclei of the same spin system. , It is an adequate technique for analyzing biomass-derived platform compounds of the hydrogenation/hydrogenolysis reaction because these molecules generally contain complete proton spin systems .…”

Section: Introductionmentioning

confidence: 99%

DOSY Plus Selective TOCSY: An Efficient NMR Combination for Analyzing Hydrogenation/Hydrogenolysis Mixtures of Biomass-Derived Platform Compounds

et al. 2018

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Analyzing the mixtures obtained from hydrogenation or hydrogenolysis reactions of biomass-derived platform chemicals is challenging work. With the development and improvement of NMR techniques, the NMR spectrometer proves to be an alternative and highly efficient piece of equipment for the rapid analysis of complex mixtures without the need for tedious purification. Herein, diffusion-ordered spectroscopy (DOSY) is applied in analyzing four model mixtures, which consist of the reactants and products from hydrogenation/hydrogenolysis reactions of biomass-derived platform chemicals. The results show that the DOSY technique can pseudoseparate most components in the model mixtures. The 1D selective gradient TOCSY technique is used as a supporting tool in the cases where the DOSY technique cannot clearly distinguish between the components of the mixtures. This is generally a problem when components in the mixture have very similar diffusion coefficients or severe overlap of peaks. The results show that DOSY and 1D selective gradient TOCSY techniques make a strong combination for complex mixture analyses.

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Combination of DOSY and 1D selective gradient TOCSY: Versatile NMR tools for identify the mixtures from glycerol hydrogenolysis reaction

Cited by 8 publications

References 38 publications

Amino Acid Ionic Liquids Catalyzed d-Glucosamine into Pyrazine Derivatives: Insight from NMR Spectroscopy

Amino Acid Ionic Liquids Catalyzed d-Glucosamine into Pyrazine Derivatives: Insight from NMR Spectroscopy

Selective excitation enables encoding and measurement of multiple diffusion parameters in a single experiment

DOSY Plus Selective TOCSY: An Efficient NMR Combination for Analyzing Hydrogenation/Hydrogenolysis Mixtures of Biomass-Derived Platform Compounds

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