Crystal structures of a pair of diastereomeric 3-(N,N-dimethylammonium)-1,1-diphenyl-1-butanol O,O′-di-p-toloyl hydrogen tartrates
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Crystal structures of a pair of diastereomeric 3-(N,N-dimethylammonium)-1,1-diphenyl-1-butanol O,O′-di-p-toloyl hydrogen tartrates. / Hansen, Lene M.; Frydenvang, Karla; Jensen, Birthe; Liljefors, Tommy.
In: Journal of Chemical Crystallography, Vol. 28, No. 7, 07.1998, p. 545-553.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Crystal structures of a pair of diastereomeric 3-(N,N-dimethylammonium)-1,1-diphenyl-1-butanol O,O′-di-p-toloyl hydrogen tartrates
AU - Hansen, Lene M.
AU - Frydenvang, Karla
AU - Jensen, Birthe
AU - Liljefors, Tommy
N1 - Funding Information: We thank Mr. Ivan Mikkelsen for providing us with the pure enantiomers of 3-(N,N-dimethylamino)-1,1-diphenyl-1-butanol. The assistance of Mr. Flem-ming Hansen with the X-ray data collection is gratefully acknowledged. We thank Mr. Per Beckman, Mr. Thomas Larsson, and Ms. Katarina Bystrom at Astra Draco, Lund, Sweden for helpingwith the Differential Scanning Calorimetry measurements. Financial support was obtained from the Lundbeck Foundation, the Danish Medical Research Council, the Alfred Benzon Foundation and the Danish State Biotechnology Programme |1991/1995|.
PY - 1998/7
Y1 - 1998/7
N2 - The crystal structures of a pair of diastereomeric salts of (-)-(2R, 3R)-O, O′-di-p-toloyl tartaric acid and (-)- and (+)-3-N,N-dimethylamino-1,1-diphenyl-1-butanol have been determined. Crystal data: 3: (-)-(R)-C18H24NO+, (-)-(2R, 3R)-C20H17O-8, orthorhombic, P212121, a = 7.873(2), b = 15.343(3), c = 28.76(1) Å, V = 3474(2) Å3, Z = 4, and Dcale = 1.254 g cm-3. 4: (+)-(S)-C18H24NO+, (-)-(2R, 3R)-C20H17O-8, orthorhombic, P212121, a = 7.504(1), b = 17.215(2), c = 26.490(4) Å, V = 3422.0(8) Å3, Z = 4, and Dcalc = 1.273 g cm-3. The geometries and the conformational energies of the solid state conformations of the cations have been compared with global and local energy minimum conformations determined by molecular mechanics calculations. In the solid state, one conformation with and one without an intramolecular hydrogen bond are observed. The calculated global energy minimum conformation in aqueous solution contains the intramolecular hydrogen bond.
AB - The crystal structures of a pair of diastereomeric salts of (-)-(2R, 3R)-O, O′-di-p-toloyl tartaric acid and (-)- and (+)-3-N,N-dimethylamino-1,1-diphenyl-1-butanol have been determined. Crystal data: 3: (-)-(R)-C18H24NO+, (-)-(2R, 3R)-C20H17O-8, orthorhombic, P212121, a = 7.873(2), b = 15.343(3), c = 28.76(1) Å, V = 3474(2) Å3, Z = 4, and Dcale = 1.254 g cm-3. 4: (+)-(S)-C18H24NO+, (-)-(2R, 3R)-C20H17O-8, orthorhombic, P212121, a = 7.504(1), b = 17.215(2), c = 26.490(4) Å, V = 3422.0(8) Å3, Z = 4, and Dcalc = 1.273 g cm-3. The geometries and the conformational energies of the solid state conformations of the cations have been compared with global and local energy minimum conformations determined by molecular mechanics calculations. In the solid state, one conformation with and one without an intramolecular hydrogen bond are observed. The calculated global energy minimum conformation in aqueous solution contains the intramolecular hydrogen bond.
KW - Conformational analysis
KW - Crystal packing
KW - Diastereomeric salts
KW - Molecular mechanics calculations
KW - O, O′-di-p-toloyl hydrogen taitrates
UR - http://www.scopus.com/inward/record.url?scp=0032272247&partnerID=8YFLogxK
U2 - 10.1023/A:1023296106521
DO - 10.1023/A:1023296106521
M3 - Journal article
AN - SCOPUS:0032272247
VL - 28
SP - 545
EP - 553
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
SN - 1074-1542
IS - 7
ER -
ID: 382747996