Comparison of Chiral and Racemic Forms of Zinc Cyclohexane trans-1,2-Dicarboxylate Frameworks: A Structural, Computational, and Calorimetric Study

被引:37
作者
Bailey, Andrew J. [2 ]
Lee, Clare [4 ]
Feller, Russell K. [3 ]
Orton, James B. [1 ]
Mellot-Draznieks, Caroline [5 ]
Slater, Ben [5 ]
Harrison, William T. A. [4 ]
Simoncic, P. [3 ]
Navrotsky, A. [6 ]
Grossel, Martin C. [2 ]
Cheetham, Anthony K. [1 ]
机构
[1] Univ Cambridge, Dept Mat Sci & Met, Cambridge CB2 3QZ, England
[2] Univ Southampton, Sch Chem, Southampton SO9 5NH, Hants, England
[3] Univ Calif Santa Barbara, Mat Res Lab, Santa Barbara, CA 93106 USA
[4] Univ Aberdeen, Dept Chem, Aberdeen AB9 1FX, Scotland
[5] UCL, Dept Chem, London WC1E 6BT, England
[6] Univ Calif Davis, Peter A Rock Thermochem Lab, Davis, CA 95616 USA
基金
美国国家科学基金会; 英国工程与自然科学研究理事会;
关键词
calorimetry; chirality; crystal engineering; molecular modeling; organic-inorganic hybrid composites;
D O I
10.1002/anie.200802564
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) An integrated study of the organic-inorganic framework material zinc cyclohexane trans-1,2-dicarboxylate involving synthesis,structure elucidation, computer simulation,and calorimetry shows that the chiral R,R form (right in picture) is less stable than its racemic R,R/S,S analogue (left) and adopts a layered structure with a fundamentally different topology. The results point to the possibility that the structural diversity of racemic frameworks and their homochiral analogues may be much greater than has hitherto been suspected. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8634 / 8637
页数:4
相关论文
共 22 条
[1]   Chiral three-dimensional microporous nickel aspartate with extended Ni-O-Ni bonding [J].
Anokhina, Ekaterina V. ;
Go, Yong Bok ;
Lee, Yongjae ;
Vogt, Thomas ;
Jacobson, Allan J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9957-9962
[2]   [Ni2O(L-Asp)(H2O)2]•4H2O:: A homochiral 1D helical chain hybrid compound with extended Ni-O-Ni bonding [J].
Anokhina, EV ;
Jacobson, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3044-3045
[3]  
[Anonymous], 2004, Angew. Chem, V116, P2388, DOI DOI 10.1016/j.jechem.2020.01.001
[4]  
Berkessel A, 2002, EUR J ORG CHEM, V2002, P2948
[5]   Permanent microporosity and enantioselective sorption in a chiral open framework [J].
Bradshaw, D ;
Prior, TJ ;
Cussen, EJ ;
Claridge, JB ;
Rosseinsky, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :6106-6114
[6]   Structural diversity and chemical trends in hybrid inorganic-organic framework materials [J].
Cheetham, Anthony K. ;
Rao, C. N. R. ;
Feller, Russell K. .
CHEMICAL COMMUNICATIONS, 2006, (46) :4780-4795
[7]   STRUCTURE AND ENERGETICS OF LIGAND-BINDING TO PROTEINS - ESCHERICHIA-COLI DIHYDROFOLATE REDUCTASE TRIMETHOPRIM, A DRUG-RECEPTOR SYSTEM [J].
DAUBEROSGUTHORPE, P ;
ROBERTS, VA ;
OSGUTHORPE, DJ ;
WOLFF, J ;
GENEST, M ;
HAGLER, AT .
PROTEINS-STRUCTURE FUNCTION AND GENETICS, 1988, 4 (01) :31-47
[8]   The interaction of water with MOF-5 simulated by molecular dynamics [J].
Greathouse, Jeffery A. ;
Allendorf, Mark D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10678-10679
[9]   Chemical and structural diversity in chiral magnesium tartrates and their racemic and Meso analogues [J].
Kam, Kinson C. ;
Young, Karen L. M. ;
Cheetham, Anthony K. .
CRYSTAL GROWTH & DESIGN, 2007, 7 (08) :1522-1532
[10]   A versatile family of interconvertible microporous chiral molecular frameworks: The first example of ligand control of network chirality [J].
Kepert, CJ ;
Prior, TJ ;
Rosseinsky, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) :5158-5168