The solid state structure of pyridinium hydrogen squarate

Modec, Barbara

doi:10.1016/j.molstruc.2015.05.056

Cited by 5 publications

(4 citation statements)

References 27 publications

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“…The hydrogen bonds are shown as dashed lines (see Table 1). (Modec, 2015) pack with a C 1 1 (5) chain motif of hydrogen squarate anions with dimer D 1 1 (2) motifs on the periphery of the hydrogen-bonded chains of hydrogen squarate anions. A more complex R 4 4 (2) tetramer hydrogenbonded ring motif is found in the structure of 1,2,3,4-tetrahydroisoquinolinium hydrogen squarate (Kolev et al, 2007).…”

Section: Figurementioning

confidence: 99%

N,N-Dibutylanilinium hydrogen squarate

2017

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ÁC 4 HO 4 À [systematic name: N,N-dibutylbenzenaminium 2-hydroxy-3,4-dioxocyclobut-1-en-1-olate], is composed of a protonated N,N-dibutylaniline cation with a hydrogen squarate monoanion (common names). The disparate bond lengths within the squarate anion suggest delocalization of the negative charge over only part of the squarate moiety. In the crystal, the squarate anions are linked by pairs of O-HÁ Á ÁO hydrogen bonds, forming inversion dimers with an R 2 2 (10) ring motif. The dimers are linked to the cations on either side by N-HÁ Á ÁO hydrogen bonds, and weak C-HÁ Á ÁO hydrogen bonds. These cation-anion-anion-cation units are linked by further C-HÁ Á ÁO hydrogen bonds, forming layers parallel to (102).

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Section: Figurementioning

confidence: 99%

N,N-Dibutylanilinium hydrogen squarate

2017

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“…Reproducible data was relatively good, and the distance of the data points at the loading plot away from the origin reflected the degree of deviation from the PC1 (relation with retention time) and PC2 (relation with absolute content). The dot labeled as 12.5685 represents a compound that was identified by the NIST 08 database and a standard sample, 3,4-dihydroxy-3-cyclobutene-1,2-dione (Modec 2015), an important fine chemical. The corresponding dots are close to the PC1 axis and away from the PC2 axis in this condition.…”

Section: Pls-da Discrimination Of Pyrolysis Products Difference At Unmentioning

confidence: 99%

Biomass Pyrolysis of Helianthus annuus Stems: Qualitative and Quantitative Study Based on Py-GC/MS

Chen¹,

Gong²,

Zhang³

et al. 2016

BioResources

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The pyrolytic product vapor of Helianthus annuus stems was analyzed by Pyrolysis-gas chromatography-mass spectrometry (Py-GC/MS) using the internal standard (ISTD) method with different pyrolysis temperatures and times. 1,3,5-tri-tert-butylbenzene (TTBB) was found to be the best ISTD chemical in this study. Scanning electron microscopy (SEM) revealed that, for the solid-state product, the pores and mesh structure gradually increased along with the pyrolysis temperatures and time. Sintering and porous destruction were observed at a lower pyrolysis temperature (600 °C) with longer time (0.5 min). The pyrolysis vapors contained small gas molecules such as CO2 as well as complex organic compounds, mainly alcohols, esters, acids, aldehydes, ketones, aromatic compounds, etc. In these products, aldehyde, ketone, and aromatic compounds were the main biochemicals; the appropriate pyrolysis temperature to produce aldehydes and ketones was 700 °C, and 600 °C was suitable for aromatic compounds. The regularity of the distribution of products and pyrolytic conditions was explored through eight representative compounds. The relationship between the product contents and pyrolysis conditions were complex for Helianthus annuus stems, but partial least squares discriminant analysis (PLS-DA) methods were a powerful tool for screening biochemicals whose absolute contents were sensitive to the pyrolysis conditions.

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“…Studies on the proton transfer between pyridine derivatives and various organic acids have been carried out in recent years (Drichko et al, 1999;Majerz & Koll, 2004;Majerz et al, 2005;Khan et al, 2011;Stilinovic ´& Kaitner, 2012;Seaton et al, 2013;Smith & Wermuth, 2013b;Thomas et al, 2013;Khalib et al, 2014;Lemmerer et al, 2015;Modec, 2015;Gaballa & Amin, 2015;Koeppe et al, 2017;Tanaka & Matsushita, 2017;Foretic et al, 2018;Amirat et al, 2019;Ma et al, 2019;de Carvalho et al, 2021;Stevens, 2022). Among these compounds, aminopyridine as a proton acceptor has been used to form proton-transfer salts with carboxylic acids and other acids as proton donors (Nazari et al, 2009;Vadivelan et al, 2015;Murugesan et al, 2015;Prakash et al, 2018;Al-Ahmary et al, 2018;Srijana et al, 2022Srijana et al, , 2023.…”

Section: Introductionmentioning

confidence: 99%

Proton-transfer salts of diphenylphosphinic acid with substituted 2-aminopyridine: crystal structure, spectroscopic and DFT studies

Yuan

Zhang

et al. 2023

Acta Crystallogr C

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Three proton-transfer salts of diphenylphosphinic acid (DPPA) with 2-amino-5-(X)-pyridine (AMPY, X = Cl, CN or CH3), namely, 2-amino-5-chloropyridinium diphenylphosphinate, C5H6ClN2 +·C12H10O2P− (1, X = Cl), 2-amino-5-cyanopyridinium diphenylphosphinate, C6H6N3 +·C12H10O2P− (2, X = CN), and 2-amino-5-methylpyridinium diphenylphosphinate, C6H9N2 +·C12H10O2P− (3, X = CH3), have been synthesized and characterized by FT–IR and 1H NMR spectroscopy, and X-ray crystallography. The crystal structures of compounds 1–3 were determined in the space group P\overline{1} for 1 and 2, and C2/c for 3. All three compounds contain N—H...O hydrogen-bonding interactions due to proton transfer from the O=P—OH group of DPPA as donor to the pyridine N atom of AMPY as acceptor. The proton transfer of compounds 1–3 was also verified by 1H NMR and FT–IR spectroscopy. The stoichiometry of all three proton-transfer salts was determined to be 1:1 and the Benesi–Hildebrand equation was applied to determine the formation constant (K CT) and the molar extinction coefficient (ɛCT) in each case. Theoretical density functional theory (DFT) calculations were performed to investigate the optimized geometries, the molecular electrostatic potentials (MEP) and the highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO) of all three proton-transfer salts. The results showed good agreement between the experimental data and the DFT computational analysis.

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The solid state structure of pyridinium hydrogen squarate

Cited by 5 publications

References 27 publications

N,N-Dibutylanilinium hydrogen squarate

N,N-Dibutylanilinium hydrogen squarate

Biomass Pyrolysis of Helianthus annuus Stems: Qualitative and Quantitative Study Based on Py-GC/MS

Proton-transfer salts of diphenylphosphinic acid with substituted 2-aminopyridine: crystal structure, spectroscopic and DFT studies

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