Optical resolution of 2-(2′-hydroxyethylamino)-1-phenylethanol, and the crystal structures of two polymorphic modifications of the (2R,3R)-O,O′-dibenzoyl hydrogen tartrate salt of the (S)-(+)-enantiomer

K. Marthi, Sine Larsen, Mária Ács, J. Bálint, E. Fogassy

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Abstract

Successful separation of the enantiomers of 2-(2′-hydroxyethylamino)-1-phenylethanol was achieved using (2R,3R)-O,O′-dibenzoyltartaric acid as a resolving agent. The less soluble salt, (S)-N-(2′-hydroxyethyl)-2-phenyl-2-hydroxyethylammonium (2R,3R)-O,O′-dibenzoyl hydrogen tartrate, was found to crystallize in two polymorphic modifications. The more stable modification is orthorhombic, space group P212121 with cell dimensions a=8.0096(8), b= 12.0536(13), c=28.063(4) Å, V = 2709.3(6) Å3, Z=4, Dx=1.323 g cm-3. X-Ray diffraction data measured at 295.7(5) K with CuKα (λ=1.541 84 Å) radiation were used for the crystal structure determination, R=0.0501 for 4951 reflections with I>2σ(I). The less stable modification is monoclinic, space group P21. X-Ray diffraction data measured at 122.0(5) K conform to a cell of a= 8.0047(8), b=11.865(2), c=28.065(5) Å, β=91.410(11)°, V=2664.7(7) Å3, Z=4, Dx=1.345 g cm-3, for CuKα. (λ=1.541 84 Å) radiation. This monoclinic crystal structure was refined to R=0.0503 for 3233 reflections with I>2σ(I); the two independent ion pairs are almost related by the pseudotranslational symmetry of c/2. Both crystal structures established that the (+)D rotation of the 2-(2′-hydroxyethylamino)-1-phenylethanol corresponds to the S enantiomer. The hydrogen bonding scheme is identical in the two modifications, leading to hydrogen bonded sheets. In the monoclinic modification each crystallographically independent ion pair forms separate sheets related by the pseudotranslational symmetry of c/2. A two-fold screw axis parallel to c relates the sheets in the orthorhombic modification.

Original languageEnglish
Pages (from-to)367-378
Number of pages12
JournalActa Chemica Scandinavica
Volume51
Issue number3 SUPPL.
Publication statusPublished - Mar 1997

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Enantiomers
Hydrogen
Salts
Crystal structure
Ions
Radiation
X ray diffraction
Crystal symmetry
Hydrogen bonds
Acids
tartaric acid
methylphenyl carbinol

ASJC Scopus subject areas

  • Chemical Engineering(all)

Cite this

@article{1c45c687553f454ebbf16325f9323e08,
title = "Optical resolution of 2-(2′-hydroxyethylamino)-1-phenylethanol, and the crystal structures of two polymorphic modifications of the (2R,3R)-O,O′-dibenzoyl hydrogen tartrate salt of the (S)-(+)-enantiomer",
abstract = "Successful separation of the enantiomers of 2-(2′-hydroxyethylamino)-1-phenylethanol was achieved using (2R,3R)-O,O′-dibenzoyltartaric acid as a resolving agent. The less soluble salt, (S)-N-(2′-hydroxyethyl)-2-phenyl-2-hydroxyethylammonium (2R,3R)-O,O′-dibenzoyl hydrogen tartrate, was found to crystallize in two polymorphic modifications. The more stable modification is orthorhombic, space group P212121 with cell dimensions a=8.0096(8), b= 12.0536(13), c=28.063(4) {\AA}, V = 2709.3(6) {\AA}3, Z=4, Dx=1.323 g cm-3. X-Ray diffraction data measured at 295.7(5) K with CuKα (λ=1.541 84 {\AA}) radiation were used for the crystal structure determination, R=0.0501 for 4951 reflections with I>2σ(I). The less stable modification is monoclinic, space group P21. X-Ray diffraction data measured at 122.0(5) K conform to a cell of a= 8.0047(8), b=11.865(2), c=28.065(5) {\AA}, β=91.410(11)°, V=2664.7(7) {\AA}3, Z=4, Dx=1.345 g cm-3, for CuKα. (λ=1.541 84 {\AA}) radiation. This monoclinic crystal structure was refined to R=0.0503 for 3233 reflections with I>2σ(I); the two independent ion pairs are almost related by the pseudotranslational symmetry of c/2. Both crystal structures established that the (+)D rotation of the 2-(2′-hydroxyethylamino)-1-phenylethanol corresponds to the S enantiomer. The hydrogen bonding scheme is identical in the two modifications, leading to hydrogen bonded sheets. In the monoclinic modification each crystallographically independent ion pair forms separate sheets related by the pseudotranslational symmetry of c/2. A two-fold screw axis parallel to c relates the sheets in the orthorhombic modification.",
author = "K. Marthi and Sine Larsen and M{\'a}ria {\'A}cs and J. B{\'a}lint and E. Fogassy",
year = "1997",
month = "3",
language = "English",
volume = "51",
pages = "367--378",
journal = "Acta Chemica Scandinavica",
issn = "0904-213X",
publisher = "Royal Society of Chemistry",
number = "3 SUPPL.",

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TY - JOUR

T1 - Optical resolution of 2-(2′-hydroxyethylamino)-1-phenylethanol, and the crystal structures of two polymorphic modifications of the (2R,3R)-O,O′-dibenzoyl hydrogen tartrate salt of the (S)-(+)-enantiomer

AU - Marthi, K.

AU - Larsen, Sine

AU - Ács, Mária

AU - Bálint, J.

AU - Fogassy, E.

PY - 1997/3

Y1 - 1997/3

N2 - Successful separation of the enantiomers of 2-(2′-hydroxyethylamino)-1-phenylethanol was achieved using (2R,3R)-O,O′-dibenzoyltartaric acid as a resolving agent. The less soluble salt, (S)-N-(2′-hydroxyethyl)-2-phenyl-2-hydroxyethylammonium (2R,3R)-O,O′-dibenzoyl hydrogen tartrate, was found to crystallize in two polymorphic modifications. The more stable modification is orthorhombic, space group P212121 with cell dimensions a=8.0096(8), b= 12.0536(13), c=28.063(4) Å, V = 2709.3(6) Å3, Z=4, Dx=1.323 g cm-3. X-Ray diffraction data measured at 295.7(5) K with CuKα (λ=1.541 84 Å) radiation were used for the crystal structure determination, R=0.0501 for 4951 reflections with I>2σ(I). The less stable modification is monoclinic, space group P21. X-Ray diffraction data measured at 122.0(5) K conform to a cell of a= 8.0047(8), b=11.865(2), c=28.065(5) Å, β=91.410(11)°, V=2664.7(7) Å3, Z=4, Dx=1.345 g cm-3, for CuKα. (λ=1.541 84 Å) radiation. This monoclinic crystal structure was refined to R=0.0503 for 3233 reflections with I>2σ(I); the two independent ion pairs are almost related by the pseudotranslational symmetry of c/2. Both crystal structures established that the (+)D rotation of the 2-(2′-hydroxyethylamino)-1-phenylethanol corresponds to the S enantiomer. The hydrogen bonding scheme is identical in the two modifications, leading to hydrogen bonded sheets. In the monoclinic modification each crystallographically independent ion pair forms separate sheets related by the pseudotranslational symmetry of c/2. A two-fold screw axis parallel to c relates the sheets in the orthorhombic modification.

AB - Successful separation of the enantiomers of 2-(2′-hydroxyethylamino)-1-phenylethanol was achieved using (2R,3R)-O,O′-dibenzoyltartaric acid as a resolving agent. The less soluble salt, (S)-N-(2′-hydroxyethyl)-2-phenyl-2-hydroxyethylammonium (2R,3R)-O,O′-dibenzoyl hydrogen tartrate, was found to crystallize in two polymorphic modifications. The more stable modification is orthorhombic, space group P212121 with cell dimensions a=8.0096(8), b= 12.0536(13), c=28.063(4) Å, V = 2709.3(6) Å3, Z=4, Dx=1.323 g cm-3. X-Ray diffraction data measured at 295.7(5) K with CuKα (λ=1.541 84 Å) radiation were used for the crystal structure determination, R=0.0501 for 4951 reflections with I>2σ(I). The less stable modification is monoclinic, space group P21. X-Ray diffraction data measured at 122.0(5) K conform to a cell of a= 8.0047(8), b=11.865(2), c=28.065(5) Å, β=91.410(11)°, V=2664.7(7) Å3, Z=4, Dx=1.345 g cm-3, for CuKα. (λ=1.541 84 Å) radiation. This monoclinic crystal structure was refined to R=0.0503 for 3233 reflections with I>2σ(I); the two independent ion pairs are almost related by the pseudotranslational symmetry of c/2. Both crystal structures established that the (+)D rotation of the 2-(2′-hydroxyethylamino)-1-phenylethanol corresponds to the S enantiomer. The hydrogen bonding scheme is identical in the two modifications, leading to hydrogen bonded sheets. In the monoclinic modification each crystallographically independent ion pair forms separate sheets related by the pseudotranslational symmetry of c/2. A two-fold screw axis parallel to c relates the sheets in the orthorhombic modification.

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