Crown ether conformations in 1,3-calix[4]arene bis(crown ethers): crystal structures of a caesium complex and solvent adducts and molecular dynamics simulations*
作者： Pierre Thuéry, , Martine Nierlich , Jeffrey C. Bryan , Véronique Lamare , Jean-François Dozol
DOI: 10.1039/A705453J
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摘要: The crystal structures of solvent adducts 1,3-calix[4]arene bis(18-crown-6) 1 and bis(naphtho-18-crown-6) 3 as well the structure caesium complex have been determined. In 1·3CH3NO2 3·3CH3CN complexed molecules their methyl group at centre crown ether rings, whereas in 3·C6H5CH3, is located voids. consequences on conformations are noticeable: comparison with previous results shows that conformation only slightly different its acetonitrile nitromethane adducts, being same potassium complexes; adduct strongly from one obtained by crystallization toluene. Molecular dynamics simulations vacuo were performed free mononuclear complex, discussed terms conformational mobility loop.
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sci-hub.se 参考文章(17)
P. Guilbaud, G. Wipff, Hydration of uranyl (UO22+) cation and its nitrate ion and 18-crown-6 adducts studied by molecular dynamics simulations The Journal of Physical Chemistry. ,vol. 97, pp. 5685- 5692 ,(1993) , 10.1021/J100123A037
A. Varnek, G. Wipff, Solvent and counterion effects on Na+Cs+ complexation selectivity by conformationally locked calix[4]-bis-crown ligands: Molecular Dynamics and Free Energy Perturbation studies in water and methanol, acetonitrile and chloroform solutions Journal of Molecular Structure-theochem. ,vol. 363, pp. 67- 85 ,(1996) , 10.1016/0166-1280(95)04425-6
P. Guilbaud, A. Varnek, G. Wipff, Molecular dynamics study of p-tert-butylcalix[4]arenetetraamide and its complexes with neutral and cationic guests. Influence of solvation on structures and stabilities Journal of the American Chemical Society. ,vol. 115, pp. 8298- 8312 ,(1993) , 10.1021/JA00071A044
Tami J. Marrone, David S. Hartsough, Kenneth M. Merz, Determination of Atomic Charges Including solvation and Conformational Effects The Journal of Physical Chemistry. ,vol. 98, pp. 1341- 1343 ,(1994) , 10.1021/J100055A048
Donald J. Cram, The Design of Molecular Hosts, Guests, and Their Complexes (Nobel Lecture)† Angewandte Chemie. ,vol. 27, pp. 1009- 1020 ,(1988) , 10.1002/ANIE.198810093
Rocco Ungaro, Alessandro Casnati, Franco Ugozzoli, Andrea Pochini, Jean-François Dozol, Clement Hill, Hélène Rouquette, 1,3‐Dialkoxycalix[4]arenecrowns‐6 in 1,3‐Alternate Conformation: Cesium‐Selective Ligands that Exploit Cation‐Arene Interactions Angewandte Chemie. ,vol. 33, pp. 1506- 1509 ,(1994) , 10.1002/ANIE.199415061
L. Troxler, G. Wipff, Conformation and Dynamics of 18-Crown-6, Cryptand 222, and Their Cation Complexes in Acetonitrile Studied by Molecular Dynamics Simulations Journal of the American Chemical Society. ,vol. 116, pp. 1468- 1480 ,(1994) , 10.1021/JA00083A036
V. Lamare, C. Bressot, J.-F. Dozol, J. Vicens, Z. Asfari, R. Ungaro, A. Casnati, Selective Extraction of Cesium at Tracer Level Concentration from a Sodium Nitrate Solution with Calix-Crowns. Molecular Modeling Study of the Cs+/Na+ Selectivity Separation Science and Technology. ,vol. 32, pp. 175- 191 ,(1997) , 10.1080/01496399708003193
Zouhair. Asfari, Christophe. Bressot, Jacques. Vicens, Clement. Hill, Jean-Francois. Dozol, Helene. Rouquette, S. Eymard, Veronique. Lamare, B. Tournois, Doubly Crowned Calix[4]arenes in the 1,3-Alternate Conformation as Cesium-Selective Carriers in Supported Liquid Membranes Analytical Chemistry. ,vol. 67, pp. 3133- 3139 ,(1995) , 10.1021/AC00114A006
Atsushi Ikeda, Seiji Shinkai, On the Origin of High Ionophoricity of 1, 3-Alternate Calix[4]arenes: π-donor Participation in Complexation of Cations and Evidence for Metal-Tunneling through the Calix[4]arene Cavity Journal of the American Chemical Society. ,vol. 116, pp. 3102- 3110 ,(1994) , 10.1021/JA00086A045