Salts of amino acids with hexafluorosilicate anion

Ghazaryan, V.V.; Fleck, Michel; Petrosyan, A.M.

doi:10.1016/j.jcrysgro.2011.11.017

Cited by 22 publications

(4 citation statements)

References 10 publications

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“…To further investigate the order‐disorder phase transition in 1 , its crystal structures were determined at 293 K and 100 K (Table S1, Supporting Information). Although the disordered crystal structure of 1 at room temperature has been reported in the literature, we reanalyze the room‐temperature structure and propose that partial disorder in the hexafluorosilicate moiety originates from its uniaxial wheel‐like rotation (please see the following structural analysis). The structure of room temperature phase (RTP, 293 K) is orthorhombic with a centrosymmetric space group of Fddd , and cell parameters of a =13.2237, b =19.3136, c =22.0443 Å, α = β = γ =90°, and V =5630.05 Å 3 .…”

Section: Resultsmentioning

confidence: 99%

“…In the present work, we found that the partial disorder of the hexafluorosilicate moiety at room temperature originates from its disntinctive uniaxial wheel‐like rotation in a hexafluorosilicate‐based crystal, bis(betainium) hexafluorosilicate bis(betaine) ( 1 ). As temperature decreases, a total freeze of this wheel‐like motion results in a second‐order phase transition at 250 K. Thermal measurements and variable‐temperature single‐crystal X‐ray diffractions confirm the solid‐state phase transition.…”

Section: Introductionmentioning

confidence: 99%

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Order-Disorder Phase Transition, Anisotropic and Switchable Dielectric Constants Induced by Freeze of the Wheel-Like Motion in a Hexafluorosilicate-Based Crystal

Liu

Sun

et al. 2016

ChemistrySelect

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An order-disorder phase transition is found in a hexafluorosilicate-based crystal, bis(betainium) hexafluorosilicate bis (betaine) (1). At room temperature, 1 crystallizes in an orthorhombic space group Fddd and the hexafluorosilicate moiety exhibits partial disorder which originates from a uniaxial wheellike rotation. As temperature decreases, a total freeze of this wheel-like motion results in a second-order phase transition at 250 K and the low temperature phase of 1 belongs to a monoclinic space group C/2c. Thermal measurements and variable-temperature single-crystal X-ray diffractions confirm that distinctive order-disorder transformation of the anionic rotor is the main driving force for the solid-state phase transition. Further, theoretical computation of potential energies for the wheel-like motion elucidates the dynamic changes in the anion from rotating to static state. Moreover, dynamic changes of the crystalline in-plane rotor give rise to anisotropic and switchable dielectric constants.[a] S.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Order-Disorder Phase Transition, Anisotropic and Switchable Dielectric Constants Induced by Freeze of the Wheel-Like Motion in a Hexafluorosilicate-Based Crystal

Liu

Sun

et al. 2016

ChemistrySelect

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“…tris(1-carboxybutane-1,4-diaminium)dinitrate bis(sulfate), BAPKIP [149]; bis(L-ornithinium) chloride nitrate sulfate, EVIJAU [111]; bis(1-carboxybutane-1,4-diaminium) dichloride sulfate, BAPKOV [110]; bis(1-carboxybutane-1,4-diaminium) dibromide sulfate, BAPKUB [110]; L-ornithinium hexafluorosilicate monohydrate, BEZQOO [108]; bis(2,5-diammoniopentanoate) hexafluorosilicate, YIGMAE [107]; L-ornithine L-aspartate hemihydrate, CAPRAM [150] and NAGLYC [151]; L-ornithine D-aspartate monohydrate, VUYHII [152]; N5-aminocarbonyl-L-ornithine dihydrate, GOTFAY [99]; TEFMIA [100]; 2,5-diammoniopentanoate 4-carboxy-2-oxobutanoate, JADGED [153]; D,L-ornithine hydrobromide ORNBDL01 [154]; ORNBDL10 [109] and QQQAOJ [155]; various measurements of L-ornithine hydrochloride: ORNHCL [155], ORNHCL11 [156]; ORNHCL12 [157] and ORNHCL13 [158]; catena-[(5-ammonio-2-(difluoromethyl)norvalinato)-(m-chloro)-dichlorocopper monohydrate IHEPES [60]; D,L-ornithinium hexabromo-selenium, ORNSEB [159]; N-(9-fluorenyl)methoxycarbonyl-L-ornithine hydrochloride diethyl ether clathrate EXOFAY [98].…”

Section: Csd and Rcsb Pdb Surveymentioning

confidence: 99%

A Supramolecular Approach to Structure-Based Design with A Focus on Synthons Hierarchy in Ornithine-Derived Ligands: Review, Synthesis, Experimental and in Silico Studies

Bojarska

Remko²,

Breza

et al. 2020

Molecules

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The success of innovative drugs depends on an interdisciplinary and holistic approach to their design and development. The supramolecular architecture of living systems is controlled by non-covalent interactions to a very large extent. The latter are prone to extensive cooperation and like a virtuoso play a symphony of life. Thus, the design of effective ligands should be based on thorough knowledge on the interactions at either a molecular or high topological level. In this work, we emphasize the importance of supramolecular structure and ligand-based design keeping the potential of supramolecular H-bonding synthons in focus. In this respect, the relevance of supramolecular chemistry for advanced therapies is appreciated and undisputable. It has developed tools, such as Hirshfeld surface analysis, using a huge data on supramolecular interactions in over one million structures which are deposited in the Cambridge Structure Database (CSD). In particular, molecular interaction surfaces are useful for identification of macromolecular active sites followed by in silico docking experiments. Ornithine-derived compounds are a new, promising class of multi-targeting ligands for innovative therapeutics and cosmeceuticals. In this work, we present the synthesis together with the molecular and supramolecular structure of a novel ornithine derivative, namely N-α,N-δ)-dibenzoyl-(α)-hydroxymethylornithine, 1. It was investigated by modern experimental and in silico methods in detail. The incorporation of an aromatic system into the ornithine core induces stacking interactions, which are vital in biological processes. In particular, rare C=O…π intercontacts have been identified in 1. Supramolecular interactions were analyzed in all structures of ornithine derivatives deposited in the CSD. The influence of substituent was assessed by the Hirshfeld surface analysis. It revealed that the crystal packing is stabilized mainly by H…O, O…H, C…H, Cl (Br, F)…H and O…O interactions. Additionally, π…π, C-H…π and N-O…π interactions were also observed. All relevant H-bond energies were calculated using the Lippincott and Schroeder H-bond model. A library of synthons is provided. In addition, the large synthons (Long-Range Synthon Aufbau Module) were considered. The DFT optimization either in vacuo or in solutio yields very similar molecular species. The major difference with the relevant crystal structure was related to the conformation of terminal benzoyl C15-C20 ring. Furthermore, in silico prediction of the extensive physicochemical ADME profile (absorption, distribution, metabolism and excretion) related to the drug-likeness and medicinal chemistry friendliness revealed that a novel ornithine derivative 1 has the potential to be a new drug candidate. It has shown good in silico absorption and very low toxicity.

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“…[1][2][3][4][5][6][7][8] This is also true for amino acids and their various derivatives. 9,10 Vivid examples are N-alkylated hydrophobic amino acids, 11 amino acid conjugates of terephthalic and benzene-1,2,3-tricarboxylic acids, 12 salts of amino acids with hexafluorosilicate anions 13 etc.…”

Section: Introductionmentioning

confidence: 99%

Intermolecular interactions and chiral crystallization effects in (1,5,3-dithiazepan-3-yl)-alkanoic acids

et al. 2016

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Crystals of (1,5,3-dithiazepan-3-yl)-alkanoic acids with achiral and chiral amino acid moieties have been obtained, and their structures were studied using a single crystal X-ray technique. Simple crystal systems, namely monoclinic, triclinic, and orthorhombic, were revealed in a series of the studied compounds. The reference 1,5,3-dithiazepan-3-ol forms head-to-head cyclic dimeric associates R 2 2 (6) via strong O-H⋯N intermolecular hydrogen bonds. The achiral 1,5,3-dithiazepanes form head-to-head cyclic dimers R 2 2 (8) between two carboxylic groups, whereas the co-crystals involve solvent molecules to constitute dimeric pairs R 3 3 (11) and R 2 2 (8) through O⋯H and N⋯H hydrogen bonds. These dimers further contribute to the aggregation of layers and stacks due to diverse H⋯H and S⋯H contacts. The chiral dithiazepanes form head-totail R 1 2 (6), R 2 2 (7), and R 2 2 (8) cyclic dimers between the carboxylic group of one molecule and the dithiazepane moiety of the other one through H⋯H, S⋯H, and O⋯H intermolecular contacts. Hirshfeld analysis has shown that S⋯H (9.2-19.8%) and O⋯H (5.4-18.2%) intermolecular hydrogen bonds as well as weak H⋯H contacts (40.2-64.0%) are predominant in all the compounds to form crystal packing. CrystEngCommThis journal is † Electronic supplementary information (ESI) available: Additional tables with some bonds and with crystal data and structure refinement of the studied compounds. Fig. 12 Fragments of the crystal packing of 7 with intermolecular contacts. View along the b axis.Fig. 13 Fragments of crystal packing of 8: (a and b) view along the c axis and (c) along the b axis. CrystEngCommPaper

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Salts of amino acids with hexafluorosilicate anion

Cited by 22 publications

References 10 publications

Order-Disorder Phase Transition, Anisotropic and Switchable Dielectric Constants Induced by Freeze of the Wheel-Like Motion in a Hexafluorosilicate-Based Crystal

Order-Disorder Phase Transition, Anisotropic and Switchable Dielectric Constants Induced by Freeze of the Wheel-Like Motion in a Hexafluorosilicate-Based Crystal

A Supramolecular Approach to Structure-Based Design with A Focus on Synthons Hierarchy in Ornithine-Derived Ligands: Review, Synthesis, Experimental and in Silico Studies

Intermolecular interactions and chiral crystallization effects in (1,5,3-dithiazepan-3-yl)-alkanoic acids

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