Structural, spectroscopic and theoretical studies of dimethylphenyl betaine complex with two molecules of 2,6-dichloro-4-nitro-phenol

Szafran, M.; Komasa, Anna; Ostrowska, Kinga; Katrusiak, Andrzej; Dega‐Szafran, Z.

doi:10.1016/j.saa.2014.10.007

Cited by 10 publications

(3 citation statements)

References 52 publications

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“…The intensity of band at 1291 cm -1 , both in the Raman and IR calculated spectra of the optimized structure 2 is very strong. Similar wavenumbers of NO2 bands were found in the spectra of complexes of dimethylphenylbetaine and piperidine-3-carboxylic acid with DCNP [17,19]. Symmetry codes: a x, y-1, z; b 2.5-x, y-0.5, -0.5-z; Table S2 in supplementary materials).…”

Section: The Short O•••h•••o Hydrogen Bond Is Characterized By a Broasupporting

confidence: 60%

“…In complexes of DCNP with zwitterionic compounds such as betaines, the proton is transferred from DCNP to the carboxylate group of betaines and the O•••O distances between the phenolate anion and protonated betaines are ca. 2.42 Å [15][16][17]. However, in the 1:1 complex of DCNP with 1-piperidineacetic acid, which can be treated as a synthetic -amino acid, the proton transfer is not observed and a short asymmetric O-H•••O hydrogen bond of 2.469(2) Å is formed.…”

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confidence: 98%

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Spectroscopic studies of the 1:1 complex of piperidine-4-carboxylic acid (isonipecotic acid) with 2,6-dichloro-4-nitrophenol

Anioła

Dega‐Szafran

Katrusiak

et al. 2016

Vibrational Spectroscopy

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Section: The Short O•••h•••o Hydrogen Bond Is Characterized By a Broasupporting

confidence: 60%

mentioning

confidence: 98%

Spectroscopic studies of the 1:1 complex of piperidine-4-carboxylic acid (isonipecotic acid) with 2,6-dichloro-4-nitrophenol

Anioła

Dega‐Szafran

Katrusiak

et al. 2016

Vibrational Spectroscopy

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“…[Symmetry codes: (i) Àx + 1, y + 1 and ClÁ Á Á interactions. Three of the four ionic crystals are three-dimensional [OBEHOS (Habata et al, 1999), SAQJOJ (Szafran et al, 1997) and XOSGET (Szafran et al, 2015)], whereas the fourth ionic crystal (XAMTOV; Dega- Szafran et al, 2005) shows a one-dimensional arrangement of chains within the packing.…”

Section: Figure 14mentioning

confidence: 99%

Cocrystals of 2,6-dichloroaniline and 2,6-dichlorophenol plus three new pseudopolymorphs of their coformers

Gerhardt

Bolte

2015

Acta Crystallogr C

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The structures of cocrystals of 2,6-dichlorophenol with 2,4-diamino-6-methyl-1,3,5-triazine, C6H4Cl2O·C4H7N5, (III), and 2,6-dichloroaniline with 2,6-diaminopyrimidin-4(3H)-one and N,N-dimethylacetamide, C6H5Cl2N·C4H6N4O·C4H9NO, (V), plus three new pseudopolymorphs of their coformers, namely 2,4-diamino-6-methyl-1,3,5-triazine-N,N-dimethylacetamide (1/1), C4H7N5·C4H9NO, (I), 2,4-diamino-6-methyl-1,3,5-triazine-N-methylpyrrolidin-2-one (1/1), C4H7N5·C5H9NO, (II), and 6-aminoisocytosine-N-methylpyrrolidin-2-one (1/1), C4H6N4O·C5H9NO, (IV), are reported. Both 2,6-dichlorophenol and 2,6-dichloroaniline are capable of forming definite synthon motifs, which usually lead to either two- or three-dimensional crystal-packing arrangements. Thus, the two isomorphous pseudopolymorphs of 2,4-diamino-6-methyl-1,3,5-triazine, i.e. (I) and (II), form a three-dimensional network, while the N-methylpyrrolidin-2-one solvate of 6-aminoisocytosine, i.e. (IV), displays two-dimensional layers. On the basis of these results, attempts to cocrystallize 2,6-dichlorophenol with 2,4-diamino-6-methyl-1,3,5-triazine, (III), and 2,6-dichloroaniline with 6-aminoisocytosine, (V), yielded two-dimensional networks, whereby in cocrystal (III) the overall structure is a consequence of the interaction between the two compounds. By comparison, cocrystal-solvate (V) is mainly built by 6-aminoisocytosine forming layers, with 2,6-dichloroaniline and the solvent molecules arranged between the layers.

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A comparative interplay between small heterorings and hypofluorous acids

Oliveira

2015

J Mol Model

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Through the B3LYP/6-311++G(d,p) calculations, theoretical studies of structural parameters, electronic properties, infrared vibration modes, and charge density topologies on the C2H4O∙∙∙HX and C2H5N∙∙∙HX (X = F or O-F) heterocylic hydrogen complexes are presented. The H-bond distances and high energies point out strong contacts and stable interactions in these complexes, and the relationships between the frequency shifts on the H-F and H-O bonds as well as O-F σ-holes with the interaction strength are the benchmarks of this current work. The computations of charge transfer amounts in light of the ChelpG and NBO approaches revealed a separation of charge density on the O-F σ-holes, whose statement is reinforced by the QTAIM descriptors. Despite that O∙∙∙H and N∙∙∙H H-bonds have been characterized as closed-shell interactions, qualitatively the appearance of a partial covalent profile also was unveiled by the QTAIM protocol.

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Structural, spectroscopic and theoretical studies of dimethylphenyl betaine complex with two molecules of 2,6-dichloro-4-nitro-phenol

Cited by 10 publications

References 52 publications

Spectroscopic studies of the 1:1 complex of piperidine-4-carboxylic acid (isonipecotic acid) with 2,6-dichloro-4-nitrophenol

Spectroscopic studies of the 1:1 complex of piperidine-4-carboxylic acid (isonipecotic acid) with 2,6-dichloro-4-nitrophenol

Cocrystals of 2,6-dichloroaniline and 2,6-dichlorophenol plus three new pseudopolymorphs of their coformers

A comparative interplay between small heterorings and hypofluorous acids

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