Controlling dynamic stereoisomerism in transition-metal folded baskets
作者： Sandra Stojanović , Daniel A. Turner , Christopher M. Hadad , Jovica D. Badjić
DOI: 10.1039/C0SC00592D
关键词:
摘要: We synthesized chiral molecular baskets (R3/S3)-1, containing three pyridine rings at the rim of a bowl-shaped platform. Each was tethered to platform via CH(CH)3 stereogenic center. In line with prior studies, we found that basket (R3)-1 would coordinate Ag(I) cation forming Ag(I)–(R3)-1 complex (ΔG° = −5.9 kcal mol−1 298.0 K). Furthermore, used spectroscopic methods (1H NMR, UV-Vis and CD) establish center R configuration in direct twisting clockwise orientation (P configuration). CD spectra Ag(I)–(R3)-1(P) were also computed (TD-DFT; BHLYP/SV(P),TZVP), showing good agreement experimental data. Controlling dynamic stereoisomerism basket-like systems is important results this study will be useful for examining relationship between recognition reactivity gated confined environments.
rsc.org
sci-hub.se 参考文章(60)
Mark Mikuls, Karola Rck-Braun, C3‐Symmetric Ligands for Catalysis Organic Synthesis Highlights IV. pp. 187- 193 ,(2008) , 10.1002/9783527619979.CH28
Dong Ju Oh, Kyo Han Ahn, Fluorescent Sensing of IP3 with a Trifurcate Zn(II)-Containing Chemosensing Ensemble System Organic Letters. ,vol. 10, pp. 3539- 3542 ,(2008) , 10.1021/OL801290G
Michele Claps, Nunziatina Parrinello, Carlos Saá, Jesús A. Varela, Salvatore Caccamese, Carlo Rosini, Assignment of the absolute configuration of (+)-5,5′,6,6′-tetrahydro-7,7′-spiro[7H-cyclopenta[b]pyridine], a new inherently chiral spiropyridine, by a nonempirical analysis of its circular dichroism spectrum Tetrahedron: Asymmetry. ,vol. 17, pp. 1387- 1393 ,(2006) , 10.1016/J.TETASY.2006.04.034
Yiming Yao, Christopher J. A. Daley, Robert McDonald, Steven H. Bergens, (R)- and (S)-1,3-Bis(diphenylphosphino)-2- ((diphenylphosphino)methyl)-1-phenylpropane ((R)- and (S)-heliphos): Solid-State and Solution Conformations of a Chiral, Tripodal Tris(phosphine) Ligand That Is Restrained to One Helical Conformation upon Coordination to a Rhodium(I) Metal Center Organometallics. ,vol. 16, pp. 1890- 1896 ,(1997) , 10.1021/OM961073N
Christian Diedrich, Stefan Grimme, Systematic Investigation of Modern Quantum Chemical Methods to Predict Electronic Circular Dichroism Spectra Journal of Physical Chemistry A. ,vol. 107, pp. 2524- 2539 ,(2003) , 10.1021/JP0275802
Jeffrey W. Lockman, Noel M. Paul, Jon R. Parquette, The role of dynamically correlated conformational equilibria in the folding of macromolecular structures. A model for the design of folded dendrimers Progress in Polymer Science. ,vol. 30, pp. 423- 452 ,(2005) , 10.1016/J.PROGPOLYMSCI.2005.01.012
Lawrence Que, William B. Tolman, Biologically inspired oxidation catalysis Nature. ,vol. 455, pp. 333- 340 ,(2008) , 10.1038/NATURE07371
Axel D. Becke, A New Mixing of Hartree-Fock and Local Density-Functional Theories Journal of Chemical Physics. ,vol. 98, pp. 1372- 1377 ,(1993) , 10.1063/1.464304
Stefan Grimme, Filipp Furche, Reinhart Ahlrichs, An improved method for density functional calculations of the frequency-dependent optical rotation Chemical Physics Letters. ,vol. 361, pp. 321- 328 ,(2002) , 10.1016/S0009-2614(02)00975-2
Jacek Gawronski, Pawel Skowronek, New Chromophores for Organic Stereochemical Analysis by Exciton- Coupled Circular Dichroism Current Organic Chemistry. ,vol. 8, pp. 65- 82 ,(2004) , 10.2174/1385272043486052