Solid state structural relation and binary melting phase diagram of (S-) and racemic 2-(2-nitro-1-phenylethyl)-1,3-diphenyl-propane-1,3-dione

Katalin Gönczi, Veronika Kudar, Zsuzsa Jászay, P. Bombicz, F. Faigl, J. Madarász

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Both the S enantiomer and the racemic (RS) forms of 2-(2-nitro-1- phenylethyl)-1,3-diphenyl-propane-1,3-dione (1) have been obtained from the same reaction media by fractional crystallization from toluene. First, the racemic compound, (R,S)-1, was precipitated (mp. 159.7 C), then, from the filtrate, (S)-1 (mp. 135.6 C) was crystallized. The absolute configuration (S) and crystal structure of (S)-1 has been solved by single crystal X-ray diffraction (R = 0.0377). (S)-1 crystallizes in the orthorhombic crystal system (space group P212121 (19), a = 10.6377(2) Å, b = 11.4348(2) Å, c = 31.3543(6) Å, Z = 8, Z′ = 2). Powder XRD pattern of the racemic crystal (R,S)-1 could be indexed in the orthorhombic space group Pbca (61) (a = 22.18(7) Å, b = 17.08(3) Å, c = 9.96(3) Å, Z = 8, Z′ = 1). Differences in secondary bonding interactions and crystal stability of both (S)-1 and (R,S)-1 were evaluated on the basis of their FTIR spectra, melting points, and enthalpies of fusion. The expected eutectic-type binary melting phase diagram of (S)-1 and (R,S)-1 crystals has been constructed based on differential scanning calorimetric (DSC) measurements and calculation of the liquidus curves according to the combination of the simplified Schröder-van Laar and Prigogine-Defay equations.

Original languageEnglish
Pages (from-to)46-52
Number of pages7
JournalThermochimica Acta
Volume580
DOIs
Publication statusPublished - Mar 20 2014

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Propane
Dione
propane
Phase diagrams
Melting
phase diagrams
melting
solid state
Crystals
crystals
Enantiomers
enantiomers
liquidus
Toluene
Crystallization
eutectics
Powders
Eutectics
melting points
Melting point

Keywords

  • Crystal structure determination
  • Dibenzoylmethane
  • Enantioselective Michael addition
  • Eutectic compositions and temperature
  • Structure-property relationship
  • trans-2-Nitrostyrene

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Condensed Matter Physics
  • Instrumentation

Cite this

Solid state structural relation and binary melting phase diagram of (S-) and racemic 2-(2-nitro-1-phenylethyl)-1,3-diphenyl-propane-1,3-dione. / Gönczi, Katalin; Kudar, Veronika; Jászay, Zsuzsa; Bombicz, P.; Faigl, F.; Madarász, J.

In: Thermochimica Acta, Vol. 580, 20.03.2014, p. 46-52.

Research output: Contribution to journalArticle

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abstract = "Both the S enantiomer and the racemic (RS) forms of 2-(2-nitro-1- phenylethyl)-1,3-diphenyl-propane-1,3-dione (1) have been obtained from the same reaction media by fractional crystallization from toluene. First, the racemic compound, (R,S)-1, was precipitated (mp. 159.7 C), then, from the filtrate, (S)-1 (mp. 135.6 C) was crystallized. The absolute configuration (S) and crystal structure of (S)-1 has been solved by single crystal X-ray diffraction (R = 0.0377). (S)-1 crystallizes in the orthorhombic crystal system (space group P212121 (19), a = 10.6377(2) {\AA}, b = 11.4348(2) {\AA}, c = 31.3543(6) {\AA}, Z = 8, Z′ = 2). Powder XRD pattern of the racemic crystal (R,S)-1 could be indexed in the orthorhombic space group Pbca (61) (a = 22.18(7) {\AA}, b = 17.08(3) {\AA}, c = 9.96(3) {\AA}, Z = 8, Z′ = 1). Differences in secondary bonding interactions and crystal stability of both (S)-1 and (R,S)-1 were evaluated on the basis of their FTIR spectra, melting points, and enthalpies of fusion. The expected eutectic-type binary melting phase diagram of (S)-1 and (R,S)-1 crystals has been constructed based on differential scanning calorimetric (DSC) measurements and calculation of the liquidus curves according to the combination of the simplified Schr{\"o}der-van Laar and Prigogine-Defay equations.",
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AU - Gönczi, Katalin

AU - Kudar, Veronika

AU - Jászay, Zsuzsa

AU - Bombicz, P.

AU - Faigl, F.

AU - Madarász, J.

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AB - Both the S enantiomer and the racemic (RS) forms of 2-(2-nitro-1- phenylethyl)-1,3-diphenyl-propane-1,3-dione (1) have been obtained from the same reaction media by fractional crystallization from toluene. First, the racemic compound, (R,S)-1, was precipitated (mp. 159.7 C), then, from the filtrate, (S)-1 (mp. 135.6 C) was crystallized. The absolute configuration (S) and crystal structure of (S)-1 has been solved by single crystal X-ray diffraction (R = 0.0377). (S)-1 crystallizes in the orthorhombic crystal system (space group P212121 (19), a = 10.6377(2) Å, b = 11.4348(2) Å, c = 31.3543(6) Å, Z = 8, Z′ = 2). Powder XRD pattern of the racemic crystal (R,S)-1 could be indexed in the orthorhombic space group Pbca (61) (a = 22.18(7) Å, b = 17.08(3) Å, c = 9.96(3) Å, Z = 8, Z′ = 1). Differences in secondary bonding interactions and crystal stability of both (S)-1 and (R,S)-1 were evaluated on the basis of their FTIR spectra, melting points, and enthalpies of fusion. The expected eutectic-type binary melting phase diagram of (S)-1 and (R,S)-1 crystals has been constructed based on differential scanning calorimetric (DSC) measurements and calculation of the liquidus curves according to the combination of the simplified Schröder-van Laar and Prigogine-Defay equations.

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KW - Eutectic compositions and temperature

KW - Structure-property relationship

KW - trans-2-Nitrostyrene

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