Developing chiral surfaces for enantioselective Chemical processing

AIChE Journal

Volumn 55, Issue 10, 2009, Pages 2484-2490

  Sholl, David S ^a   Gellman, Andrew J ^b  

^a Georgia Institute of Technology   (United States)

^b CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

Asymmetric synthesis; Chirality; Chromatography; Surfaces

Indexed keywords

EID: 70349139694     PISSN: 00011541     EISSN: 15475905     Source Type: Journal    
DOI: 10.1002/aic.12036     Document Type: Article

References (35)

1. Rekoske JE. Chiral Separations. AIChE J. 2001;47:2-5.
2. Erb S. Single-enantiomer drugs poised for further market growth. Pharm Technol. 2006;30:S14.
3. Ahuja, S. Chiral Separations by Chromatography. Oxford University Press; 1999.
4. Jacoby M. Chiral catalysis at surfaces. Chem Eng News. 2004;82:37-41.
5. Hazen RM, Sholl, DS. Chiral selection on inorganic crystalline surfaces. Nat Mater. 2003;2:367-374.
6. Hazen RM. Mineral surfaces and the prebiotic selection and organization of biomolecules. Am Mineral. 2006;91: 1715-1729.
7. Halasyamani PS, Poeppelmeier KR. Noncentrosymmetric oxides. Chem Mater. 1998;10:2753-2769.
8. McFadden CF, Cremer PS, Gellman AJ. Adsorption of chiral alcohols on "chiral" metal surfaces. Langmuir. 1996;12:2483-2487
9. Sholl DS. Adsorption of chiral hydrocarbons on chiral platinum surfaces. Langmuir. 1998;14:862-867.
10. Francis AJ, Salvador PA. Chirally oriented heteroepitax- ial thin films grown by pulsed laser deposition: Pt(621) on SrTiO3(621). J Appl Phys. 2004;96:2482-2493
11. Sholl DS, Asthagiri A, Power TD. Naturally chiral metal surfaces as enantiospecific adsorbents. J Phys Chem B. 2001;105:4771-4782
12. Wang M, Xie M -H, Wu C -D, Wang Y -G. From one to three: a serine derivate manipulated homochiral metal-organic framework. Chem Commun. 2009;17:2396-2398
13. Dryzun C, Mastai Y, Shvalb A, Avnir, D. Chiral silicate zeolites. J Mater Chem. 2009;19:2062-2069.
14. Blaser HU, Pugin B, Spindler F. Progress in enantiose- lective catalysis assessed from an industrial point of view. J Mol CatalA-Chem. 2004;231:1-20
15. Keane MA. Interaction of optimcally active tartaric acid with a nickel-silica catalyst: Role of both the modification and reaction media in determining enantioselectiv- ity. Langmuir. 1997;13:41-50
16. Vargas A, Ferri D, Baiker A. DFT and ATR-IR insight into the conformational flexibility of cinchonidine adsorbed on platinum: Proton exchange with metal. J Catal. 2005;236:1-8
17. Ernst K.-H. Supramolecular surface chirality. Top Curr Chem. 2006;265:209-252.
18. Bonner WA, Kavasman PR, Martin FS. Asymmetric adsorption of alanine by quartz. Science. 1974;186:143-144.
19. Soai, K. et al. d- and l-quartz-promoted highly enantiose- lective synthesis of a chiral organic compound. JAm Chem Soc. 1999;121:11235-11236
20. Hazen RM, Filley TR, Goodfriend GA. Selective adsorption of L- and D-amino acids on calcite: Implications for bioChemical homochirality. Proc Natl Acad Sci USA. 2001;98:5487-5490
21. Han JW, Sholl DS. Enantiospecific adsorption of amino acids on hydroxylated quartz (0001). Langmuir. 2009; in press. 10.21/la901264e.
22. Jenkins SJ, Pratt SJ. Beyond the surface atlas: A road-map and gazetteer for surface symmetry and structure. Surf Sci Rep2007;62:373-429
23. Power TD, Asthagiri A, Sholl DS. Atomically detailed models of the effect of thermal roughening on the enan- tiospecificity of naturally chiral platinum surfaces. Langmuir. 2002;18:3737-3748
24. Baber AE, Gellman AJ, Sholl DS, Sykes ECH. The real structure of naturally chiral Cu{643}. J Phys Chem C. 2008;112:11086-11089
25. Horvath JD, Baker L, Gellman AJ. Enantiospecific orientation of R-3-methylcyclohexanone on the chiral Cu(643)(R/ S) surfaces. J Phys ChemC. 2008;112:7637-7643
26. Horvath JD, Koritnik, KamakotiP, Sholl DS, Gellman AJ. Enantioselective separation on a naturally chiral surface. J Am Chem Soc. 2004;126:14988-14994
27. James JN, Sholl DS. Theoretical studies of chiral adsorption on solid surfaces. Curr Opin Colloid Interface Sci. 2008;13:60-64
28. Rampulla DM, Gellman AJ. Enantioselective decomposition of chiral alkyl bromides on Cu(643)(R&S): Effects of moving the chiral center. Surf Sci. 2006;600;2823-2829
29. Attard GA. ElectroChemical studies of enantioselectivity at chiral metal surfaces. J Phys Chem B. 2001;105: 3158-3167.
30. Zhao XY. Fabricating homochiral facets on Cu(001) with L-lysine. J Am Chem Soc. 2000;122:12584-12585.
31. Claassen, J. H. & Thieme, C. L. H. Magnetic properties of Ni-based substrates for HTS tape. Supercond Sci Technol. 2008;21:105003
32. Widmer R, et al. Surface chirality of CuO thin films. J Am Chem Soc. 2006;128:14103-14108.
33. Pizzarello S. The Chemistry of life's origin: a carbonaceous meteorite perspective. Acc Chem Res. 2006;39: 231-237.
34. Kondepudi DK, Kaufman RJ, Singh N. Chiral symmetry breaking in sodium chlorate crystallization. Science. 1990;250:975-976
35. Lavabre D, Micheau JC, Islas JR, Buhse T. Kinetic insight into specific features of the autocatalytic Soai reaction. Top Curr Chem. 2008;284:67-96