Laura Bereczki

Budapest University of Technology and Economics, Budapest, Budapest fovaros, Hungary

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Publications (8)10.99 Total impact

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    ABSTRACT: In order to study the effects of crystal structures on resolvabil-ity, a CSD (Cambridge Crystallographic Database) study has been carried out on 1-phenylethylammonium diastereomeric salt pairs with available crystal structures. The structures of the diastereomers of the salts are analyzed, compared and grouped. The structural features are set against the resolution results. The effects of three types of structural features on the resolution effi-ciency are demonstrated.
    Chemical Engineering. 01/2009; 532:71-76.
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    ABSTRACT: The resolution of racemic ibuprofen was studied by partial diastereomer salt formation. The resolution was performed via two methods: resolution with (+)-(R)-phenylethylamine as chiral agent and resolution with a mixture of (+)-(R)-phenylethylamine and benzylamine. The diastereomers and unreacted enantiomers were separated by supercritical fluid extraction with carbon dioxide at 15 MPa and 33 degrees C. The influence of the achiral benzylamine on the resolution efficiency was studied by varying the concentrations of the structurally related amines in their mixtures, keeping the sum molar ratio of the amines to racemic ibuprofen constant at 0.55 +/- 0.02. The presence of benzylamine positively influenced the resolution efficiency at certain concentrations. The crystal structure of the salts of (+)-(R)-phenylethylamine with (-)-(R)-ibuprofen and (+)-(S)-ibuprofen, respectively, as well as the cocrystal of the benzylamine-ibuprofen salt with neutral ibuprofen molecules are presented. These structures were determined by single crystal X-ray diffraction, proving the significantly different stoichiometry of the related amines with the chiral acid, in accordance with mass balance calculations.
    Chirality 11/2008; 21(6):628-36. · 1.72 Impact Factor
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    ABSTRACT: Optical resolution methods were established for racemic 1-(1-naphthyl) ethylamine. The resolving agents were synthesized by N-derivatizing (R)-1-(1-naphthyl) ethylamine with dicarboxylic acids. Oxalic, malonic, and succinic acid derivatives were found to be suitable resolving agents. These resolutions are parallel to a series of optical resolutions of 1-phenylethylamine which had been previously performed by our research group using similar derivative resolving agents (Balint et al., Tetrahedron: Asymmetry 2001;12:1511-1518.) The comparison of the results of the enantiomer separations is performed. The diastereomeric salts formed with (R)-N-[1-(1-naphthyl)ethyl]oxalamic acid were investigated by single crystal X-ray diffraction. The crystal structures were compared with the previously published structures of the diastereomers of the phenyl-substituted analogue, namely (R)- and (S)-1-phenylethylammonium (R)-N-(1-phenylethyl)oxalamates (Balint et al., Tetrahedron: Asymmetry 2001;12:1511-1518).
    Chirality 07/2008; 21(3):331-8. · 1.72 Impact Factor
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    ABSTRACT: Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dicarboxilic acid derivatized resolving agents of racemic 1-phenylethylamine. Resolution results obtained with the oxalic, malonic, and succinic acid derivatives were previously discussed(1). Each of the above derivative resolving agents could be successfully applied as resolving agents of 1-phenylethylamine. The efficiency of the present optical resolution using (+)-(R)-N-(1-phenylethyl)glutaramic acid resolving agent was remarkably inferior to the results obtained by its shorter chained homologues(1). Use of achiral additives, like urea, thiourea, N-methylurea, and N,N'-dimethylurea caused large increase in the efficiency of the resolution by (+)-(R)-N-(1-phenylethyl)glutaramic acid resolving agent. Precipitated salts obtained in the resolutions performed in the presence of the additives were investigated by thermoanalysis, X-ray powder diffraction, and optical microscopy. Based on the analytical data, the improvement of the resolution results was attributed to the influence of the additives on the crystal nucleation processes of the diasteromeric salts.
    Chirality 04/2007; 19(3):239-44. · 1.72 Impact Factor
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    ABSTRACT: The efficiency of the resolution of N-formylphenylalanine was remarkably improved using (S)-(+)-2-benzylaminobutanol resolving agent in acetone. The efficiency of the resolution strongly depended on the quality of the solvent. Nevertheless, solvate formation did not occur during the process. The nature of the solvent-dependence was studied. The solid-melt binary phase diagram of the diastereomeric salts formed during the resolution by (S)-(+)-2-benzylaminobutanol was measured and discussed. It was recognized that the (S)-(+)-benzylaminobutanol (S)-(+)-N-formylphenylalanine salt exists in two polymorphic modifications.The effect of structurally related chiral and achiral auxiliary reagents in the above resolution was also studied. Thus, (S)-(+)-2-benzylaminobutanol was applied together with an (R)-(+)-1-phenylethylamine auxiliary resolving agent and benzylamine was used as a half-equivalent achiral basic reagent in a Pope–Peachey type resolution of N-formylphenylalanine by (S)-(+)-2-benzylaminobutanol. The results are compared to those obtained by the structurally related (R)-(+)-1-phenylethylamine chiral auxiliary.
    Tetrahedron Asymmetry 01/2007; 18(21):2531-2536. · 2.12 Impact Factor
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    ABSTRACT: Optical resolution of racemic-phenylalanine through its N-formyl derivative with a 1-phenylethylamine resolving agent is an effective procedure. Differential scanning calorimetry, single crystal X-ray diffraction and optical microscopy were used in the investigation of the resolution process. It was found that the thermodynamic properties of the given system would not allow the efficient enantiomer separation. Kinetic effects during the crystal formation have been discovered by the comparison of the crystal morphologies of the two diastereomers. The crystal structure of the less soluble diastereomer (S)-(−)-1-phenylethylammonium (S)-(+)-N-formylphenylalaninate salt has been determined and discussed.
    Tetrahedron Asymmetry 01/2007; 18(2):260-264. · 2.12 Impact Factor
  • Laura Bereczki, Katalin Marthi, P. Huszthy, G. Pokol
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    ABSTRACT: Thermochemical properties of crown ether complexes have been studied by simultaneous TG-DTA (thermogravimetric analysis-differential thermal analysis) coupled with a mass spectrometer, DSC (differential scanning calorimetry) and hot stage microscopy (HSM).The examined complexes contain benzylammonium- [BA], (R)-(+)-α-phenylethylammonium- [(R)-PEA], (R)-(+)- and (S)-(−)-α-(1-naphthyl)ethylammonium perchlorate [(R)-NEA and (S)-NEA] salts as guests. In the cases of BA and (R)-PEA an achiral pyridono-18-crown-6 ligand [P18C6], and in the case of (R)-NEA and (S)-NEA a chiral (R,R)-dimethylphenazino-18-crown-6 ligand [(R,R)-DMPh18C6] was used as host molecule to obtain four different crown ether complexes.In all cases, the melting points of the complexes were higher than those of both the host and the guest compounds. The decomposition of the complexes begins immediately after their melting is completed, while the BA and (R)-PEA salts and the crown ether ligands are thermally stable by 50 to 100 K above their melting points. During the decomposition of the salts and the four complexes strongly exothermic processes can be observed which are due to oxidative reactions of the perchlorate anion. Ammonium perchlorate crystals were identified among the decomposition residues of the salts.P18C6 was observed to crystallize with two molecules of water. The studied complexes of P18C6 did not contain any solvate.BA was observed to exhibit a reversible solid-solid phase transition upon heating.The heterochiral complex consisting of (S)-NEA and (R,R)-DMPh18C6 shows a solid-solid phase transition followed by two melting points. HSM observations identified three crystal modifications, two of them simultaneously co-existing.
    Journal of Thermal Analysis and Calorimetry 01/2004; 78(2). · 1.60 Impact Factor
  • Source
    Laura Bereczki, Katalin Marthi, György Pokol
    [Show abstract] [Hide abstract]
    ABSTRACT: In order to study the e ects of crystal structures on resolvabil- ity, a CSD (Cambridge Crystallographic Database) study has been carried out on 1-phenylethylammonium diastereomeric salt pairs with available crystal structures. The structures of the diastereomers of the salts are analyzed, compared and grouped. The structural features are set against the resolution results. The e ects of three types of structural features on the resolution e - ciency are demonstrated.

Publication Stats

11 Citations
10.99 Total Impact Points

Institutions

  • 2004–2008
    • Budapest University of Technology and Economics
      • • Department of Inorganic and Analytical Chemistry
      • • Department of Organic Chemistry and Technology
      Budapest, Budapest fovaros, Hungary
  • 2007
    • Hungarian Academy of Sciences
      Budapeŝto, Budapest, Hungary