Phase transition in non-centrosymmetric 2-methyl-5-nitroanilinium dihydrogen phosphate: structural, spectroscopic and optical studies

Medviediev, Volodymyr V.; Baran, J.; Zarȩba, Jan K.; Drozd, M.; Daszkiewicz, Marek

doi:10.1007/s11224-019-01480-0

Cited by 5 publications

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“…Thus, the ammonium group forms charge-assisted hydrogen bonds, which play a basic role in the molecular self-assembly and crystal growth of nitroanilinium salts (Daszkiewicz & Mielcarek, 2016;Dinesh et al, 2008;Masse & Levy, 1991;Azumi et al, 1996;Arjunan et al, 2012;Lemmerer & Billing, 2006;Daszkiewicz, 2013aDaszkiewicz, , 2014aDaszkiewicz, ,b, 2015. In the nitroanilines containing only one ammonium group, hydrogen-bonding patterns along three dimensions are not observed, but layer or ladder patterns are formed (Medviediev et al, 2020a;Medviediev & Daszkiewicz, 2019. This fact is probably associated with the molecular structures of such nitroanilines.…”

Section: Graph-set Analysis Of Hydrogen-bonding Patternsmentioning

confidence: 94%

“…Using mathematical operations on the graph-set descriptors gives an opportunity to investigate similarities and differences among the patterns in various crystal structures (Medviediev & Daszkiewicz, 2019;Daszkiewicz, 2013a). In addition, this method was applied successfully in the analysis of hydrogen-bonding patterns during phase transition (Rejnhardt et al, 2019(Rejnhardt et al, , 2020Medviediev et al, 2020a). In the present work, a thorough analysis of the patterns was studied by means of the algebraic approach for graph-set descriptors.…”

Section: Introductionmentioning

confidence: 99%

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Structural and theoretical analysis of 2-chloro-4-nitroaniline and 2-methyl-6-nitroaniline salts

Medviediev

Daszkiewicz

2021

Acta Crystallogr C

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The crystal structures of five new salts of 2-chloro-4-nitroaniline (2Cl4na) and 2-methyl-6-nitroaniline (2m6na) with inorganic acids, namely, 2-chloro-4-nitroanilinium bromide, C6H6ClN2O2 +·Br− (1), 2-chloro-4-nitroanilinium hydrogen sulfate, C6H6ClN2O2 +·HSO4 − (2), 2-methyl-6-nitroanilinium bromide, C7H9N2O2 +·Br− (3), 2-methyl-6-nitroanilinium triiodide, C7H9N2O2 +·I3 − (4), and 2-methyl-6-nitroanilinium hydrogen sulfate, C7H9N2O2 +·HSO4 − (5), were determined by single-crystal X-ray diffraction. Theoretical calculations of the relaxed potential energy surface (rPES) revealed that the energy barriers for the rotation of the nitro group for isolated H2Cl4na+ and H2m6na+ cations are 4.6 and 11.6 kcal mol−1, respectively. The ammonium group and respective anions form hydrogen bonds which are the most important interactions and are arranged in zero- (in 3), one- (in 1 and 4) or two-dimensional (in 2 and 5) networks. Hydrogen-bonding patterns were analyzed by means of mathematical relationships between graph-set descriptors and compared with previously reported nitroaniline salts. Hirshfeld surface analysis indicates that the nitro group plays a dominant role among the weak interactions, i.e. C—H...O(NO2), NO2...π(Ar) and O(NO2)...π(NO2). The frequency of the νsNO2 vibration is correlated with the type of interaction in which the NO2 group is involved. Analysis of the νsNO2 band observed in the IR and Raman spectra allowed an assessment of its shift in the sequence (H2m6na)I3 (4) < (H2m6na)HSO4 (5) < (H2m6na)Br (3) < (H2Cl4na)Br (1) < (H2Cl4na)HSO4 (2).

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