(+)-syn-Benzotriborneol an enantiopure C3-symmetric receptor for water.
作者： Fabrizio Fabris , Ottorino De Lucchi , Ilaria Nardini , Marco Crisma , Andrea Mazzanti
DOI: 10.1039/C2OB06774A
关键词: Hydrogen bond 、 Molecule 、 Enantiopure drug 、 Crystallography 、 Stereochemistry 、 Neutron diffraction 、 Supramolecular chemistry 、 Receptor 、 Acceptor 、 Chemistry
摘要: (+)-syn-Benzotriborneol forms stable complexes with one molecule of water. This is due to the ability host form three hydrogen bonds water, act simultaneously as a hydrogen-bond acceptor and donor, perfect geometrical match between pair. We report experimental (X-ray neutron diffraction, VT NMR, DSC, TGA) stereochemical studies carried out elucidate quantify molecular thermodynamic aspects this supramolecular complex.
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sci-hub.se 参考文章(49)
J.C. Buffet, J.F. Clergeau, R.G. Cooper, J. Darpentigny, A. De Laulany, C. Fermon, S. Fetal, F. Fraga, B. Guérard, R. Kampmann, A. Kastenmueller, G.J. Mc Intyre, G. Manzin, F. Meilleur, F. Millier, N. Rhodes, L. Rosta, E. Schooneveld, G.C. Smith, H. Takahashi, P. Van Esch, T.L. Van Vuure, K. Zeitelhack, Advances in detectors for single crystal neutron diffraction Nuclear Instruments & Methods in Physics Research Section A-accelerators Spectrometers Detectors and Associated Equipment. ,vol. 554, pp. 392- 405 ,(2005) , 10.1016/J.NIMA.2005.08.018
Mladen Zinic, Vinko Skaric, Amino acid containing macrocycles. Synthesis, complexation of water, and transport and binding of metal cations Journal of Organic Chemistry. ,vol. 53, pp. 2582- 2588 ,(1988) , 10.1021/JO00246A034
Christian M. Stegmann, Daniel Seeliger, George M. Sheldrick, Bert L. de Groot, Markus C. Wahl, The Thermodynamic Influence of Trapped Water Molecules on a Protein-Ligand Interaction Angewandte Chemie. ,vol. 48, pp. 5207- 5210 ,(2009) , 10.1002/ANIE.200900481
Manuel Ellermann, Roland Jakob-Roetne, Christian Lerner, Edilio Borroni, Daniel Schlatter, Doris Roth, Andreas Ehler, Markus���Georg Rudolph, Fran��ois Diederich, Molecular Recognition at the Active Site of Catechol‐O‐Methyltransferase: Energetically Favorable Replacement of a Water Molecule Imported by a Bisubstrate Inhibitor Angewandte Chemie. ,vol. 48, pp. 9092- 9096 ,(2009) , 10.1002/ANIE.200904410
Cristiano Zonta, Fabrizio Fabris, Ottorino De Lucchi, The pyrrole approach toward the synthesis of fully functionalized cup-shaped molecules. Organic Letters. ,vol. 7, pp. 1003- 1006 ,(2005) , 10.1021/OL047569F
Susan E. Gibson, M. Paola Castaldi, C3 Symmetry: Molecular Design Inspired by Nature Angewandte Chemie. ,vol. 45, pp. 4718- 4720 ,(2006) , 10.1002/ANIE.200600776
Chaesang Ihm, Youngyong In, Youngja Park, Kyungsoo Paek, Small cavitands specifically binding a water molecule. Organic Letters. ,vol. 6, pp. 369- 372 ,(2004) , 10.1021/OL036206X
Fabrizio Fabris, Leonardo Pellizzaro, Cristiano Zonta, Ottorino De Lucchi, A NovelC3-Symmetric Triol as Chiral Receptor for Ammonium Ions European Journal of Organic Chemistry. ,vol. 2007, pp. 283- 291 ,(2007) , 10.1002/EJOC.200600673
Adrian P Bisson, Christopher A Hunter, Juan Carlos Morales, Karen Young, None, COOPERATIVE INTERACTIONS IN A TERNARY MIXTURE Chemistry: A European Journal. ,vol. 4, pp. 845- 851 ,(1998) , 10.1002/(SICI)1521-3765(19980515)4:5<845::AID-CHEM845>3.0.CO;2-#
Zheng Li, Themis Lazaridis, Water at biomolecular binding interfaces Physical Chemistry Chemical Physics. ,vol. 9, pp. 573- 581 ,(2007) , 10.1039/B612449F