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Design and supramolecular structure of crystal associates of polyfluoroarylenediamines and 18-crown-6 (2 : 1). / Vaganova, Tamara A.; Gatilov, Yurij V.; Malykhin, Sergej E. и др.

в: Journal of Molecular Structure, Том 1133, 05.04.2017, стр. 122-134.

Результаты исследований: Научные публикации в периодических изданияхстатьяРецензирование

Harvard

Vaganova, TA, Gatilov, YV, Malykhin, SE, Pishchur, DP, Larichev, YV, Rodionov, VI & Malykhin, EV 2017, 'Design and supramolecular structure of crystal associates of polyfluoroarylenediamines and 18-crown-6 (2: 1)', Journal of Molecular Structure, Том. 1133, стр. 122-134. https://doi.org/10.1016/j.molstruc.2016.11.091

APA

Vaganova, T. A., Gatilov, Y. V., Malykhin, S. E., Pishchur, D. P., Larichev, Y. V., Rodionov, V. I., & Malykhin, E. V. (2017). Design and supramolecular structure of crystal associates of polyfluoroarylenediamines and 18-crown-6 (2: 1). Journal of Molecular Structure, 1133, 122-134. https://doi.org/10.1016/j.molstruc.2016.11.091

Vancouver

Vaganova TA, Gatilov YV, Malykhin SE, Pishchur DP, Larichev YV, Rodionov VI и др. Design and supramolecular structure of crystal associates of polyfluoroarylenediamines and 18-crown-6 (2: 1). Journal of Molecular Structure. 2017 апр. 5;1133:122-134. doi: 10.1016/j.molstruc.2016.11.091

Author

Vaganova, Tamara A. ; Gatilov, Yurij V. ; Malykhin, Sergej E. и др. / Design and supramolecular structure of crystal associates of polyfluoroarylenediamines and 18-crown-6 (2 : 1). в: Journal of Molecular Structure. 2017 ; Том 1133. стр. 122-134.

BibTeX

@article{5f3439cb7dfe41c2b683d715a6e1f520,
title = "Design and supramolecular structure of crystal associates of polyfluoroarylenediamines and 18-crown-6 (2: 1)",
abstract = "The possibility of co-crystallization of polyfluoroaromatic meta-diamines with 18-crown-6 in the 2:1 ratio was tested using a large group of substrates with various frameworks (benzene, naphthalene, and pyridine) and substituents (H, Cl, CF3). Co-crystals of 2:1 stoichiometry were obtained from hexafluoro-2,7-naphthylenediamine, 4-trifluoromethyltrifluoro- and 2-trifluoromethyl-4,6-difluro-1,3-phenylenediamines, 4-chlorodifluoro-2,6-diaminopyridine. According to X-ray crystallographic data, associates of CF3-containing polyfluorophenylenediamines are 2D assemblies connected via synthon Сar–N–H … Ocr. Polyfluorinated 2,7-diaminonaphthalene and 2,6-diamino-4-chloropyridine form 1D assemblies, in which the π-stacking of the naphthylenediamine molecules and the hydrogen bond Сar–N–H … Npy, respectively, are the additional structure-supporting interactions. The co-crystallization of 18-crown-6 with less electron withdrawing arylenediamines gives only associates of stoichiometry 1:1 irrespective of the components ratio and the solvent nature. To rationalize the different co-crystallization behavior of the arylenediamines, the co-crystal structures were studied using a special version of the DFT, which accounts for the van der Waals interactions. The calculated difference between the specific sublimation enthalpies for the 1:1 and 2:1 associates was suggested to be a measure of the preferable co-crystallization ratio: the both types of associates are formed when |ΔΔHsubl| is smaller than 15 J g−1, a higher value indicates a significant energy preference for one of the structures. The experimental melting enthalpy values (DSC data) for the 1:1 and 2:1 co-crystals based on the same diamine are quite similar.",
keywords = "18-crown-6, Crystal melting enthalpy, Polyfluorinated arylenediamines, Supramolecular associates, vdW-DFT calculations, X-ray diffraction analysis, COMPLEXES, LIQUID-AMMONIA, SOLID-STATE, NEUTRAL MOLECULES, HYDROGEN-BONDS, 1,2-BIS(4-PYRIDYL)ETHANE, ANHYDROUS AMMONIA, 1D ASSEMBLIES, PI-PI INTERACTIONS, ARYLENEDIAMINES",
author = "Vaganova, {Tamara A.} and Gatilov, {Yurij V.} and Malykhin, {Sergej E.} and Pishchur, {Denis P.} and Larichev, {Yurii V.} and Rodionov, {Vladimir I.} and Malykhin, {Evgenij V.}",
note = "Publisher Copyright: {\textcopyright} 2016 Elsevier B.V.",
year = "2017",
month = apr,
day = "5",
doi = "10.1016/j.molstruc.2016.11.091",
language = "English",
volume = "1133",
pages = "122--134",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Design and supramolecular structure of crystal associates of polyfluoroarylenediamines and 18-crown-6 (2

T2 - 1)

AU - Vaganova, Tamara A.

AU - Gatilov, Yurij V.

AU - Malykhin, Sergej E.

AU - Pishchur, Denis P.

AU - Larichev, Yurii V.

AU - Rodionov, Vladimir I.

AU - Malykhin, Evgenij V.

N1 - Publisher Copyright: © 2016 Elsevier B.V.

PY - 2017/4/5

Y1 - 2017/4/5

N2 - The possibility of co-crystallization of polyfluoroaromatic meta-diamines with 18-crown-6 in the 2:1 ratio was tested using a large group of substrates with various frameworks (benzene, naphthalene, and pyridine) and substituents (H, Cl, CF3). Co-crystals of 2:1 stoichiometry were obtained from hexafluoro-2,7-naphthylenediamine, 4-trifluoromethyltrifluoro- and 2-trifluoromethyl-4,6-difluro-1,3-phenylenediamines, 4-chlorodifluoro-2,6-diaminopyridine. According to X-ray crystallographic data, associates of CF3-containing polyfluorophenylenediamines are 2D assemblies connected via synthon Сar–N–H … Ocr. Polyfluorinated 2,7-diaminonaphthalene and 2,6-diamino-4-chloropyridine form 1D assemblies, in which the π-stacking of the naphthylenediamine molecules and the hydrogen bond Сar–N–H … Npy, respectively, are the additional structure-supporting interactions. The co-crystallization of 18-crown-6 with less electron withdrawing arylenediamines gives only associates of stoichiometry 1:1 irrespective of the components ratio and the solvent nature. To rationalize the different co-crystallization behavior of the arylenediamines, the co-crystal structures were studied using a special version of the DFT, which accounts for the van der Waals interactions. The calculated difference between the specific sublimation enthalpies for the 1:1 and 2:1 associates was suggested to be a measure of the preferable co-crystallization ratio: the both types of associates are formed when |ΔΔHsubl| is smaller than 15 J g−1, a higher value indicates a significant energy preference for one of the structures. The experimental melting enthalpy values (DSC data) for the 1:1 and 2:1 co-crystals based on the same diamine are quite similar.

AB - The possibility of co-crystallization of polyfluoroaromatic meta-diamines with 18-crown-6 in the 2:1 ratio was tested using a large group of substrates with various frameworks (benzene, naphthalene, and pyridine) and substituents (H, Cl, CF3). Co-crystals of 2:1 stoichiometry were obtained from hexafluoro-2,7-naphthylenediamine, 4-trifluoromethyltrifluoro- and 2-trifluoromethyl-4,6-difluro-1,3-phenylenediamines, 4-chlorodifluoro-2,6-diaminopyridine. According to X-ray crystallographic data, associates of CF3-containing polyfluorophenylenediamines are 2D assemblies connected via synthon Сar–N–H … Ocr. Polyfluorinated 2,7-diaminonaphthalene and 2,6-diamino-4-chloropyridine form 1D assemblies, in which the π-stacking of the naphthylenediamine molecules and the hydrogen bond Сar–N–H … Npy, respectively, are the additional structure-supporting interactions. The co-crystallization of 18-crown-6 with less electron withdrawing arylenediamines gives only associates of stoichiometry 1:1 irrespective of the components ratio and the solvent nature. To rationalize the different co-crystallization behavior of the arylenediamines, the co-crystal structures were studied using a special version of the DFT, which accounts for the van der Waals interactions. The calculated difference between the specific sublimation enthalpies for the 1:1 and 2:1 associates was suggested to be a measure of the preferable co-crystallization ratio: the both types of associates are formed when |ΔΔHsubl| is smaller than 15 J g−1, a higher value indicates a significant energy preference for one of the structures. The experimental melting enthalpy values (DSC data) for the 1:1 and 2:1 co-crystals based on the same diamine are quite similar.

KW - 18-crown-6

KW - Crystal melting enthalpy

KW - Polyfluorinated arylenediamines

KW - Supramolecular associates

KW - vdW-DFT calculations

KW - X-ray diffraction analysis

KW - COMPLEXES

KW - LIQUID-AMMONIA

KW - SOLID-STATE

KW - NEUTRAL MOLECULES

KW - HYDROGEN-BONDS

KW - 1,2-BIS(4-PYRIDYL)ETHANE

KW - ANHYDROUS AMMONIA

KW - 1D ASSEMBLIES

KW - PI-PI INTERACTIONS

KW - ARYLENEDIAMINES

UR - http://www.scopus.com/inward/record.url?scp=84999666606&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2016.11.091

DO - 10.1016/j.molstruc.2016.11.091

M3 - Article

AN - SCOPUS:84999666606

VL - 1133

SP - 122

EP - 134

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

ER -

ID: 9068945