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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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.
Originalsprog | Engelsk |
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Tidsskrift | Journal of Chemical Crystallography |
Vol/bind | 28 |
Udgave nummer | 7 |
Sider (fra-til) | 545-553 |
Antal sider | 9 |
ISSN | 1074-1542 |
DOI | |
Status | Udgivet - jul. 1998 |
Bibliografisk note
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|.
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