Induced chirality in achiral media - How theory unravels mysterious solvent effects

Angewandte Chemie - International Edition

Volumn 46, Issue 41, 2007, Pages 7738-7740

  Neugebauer, Johannes ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Chirality; Density functional calculations; Solvent effects

Indexed keywords

BENZENE; DENSITY FUNCTIONAL THEORY; OPTICAL ROTATION; ORGANIC SOLVENTS; QUANTUM CHEMISTRY;

ACHIRAL MEDIAS; CHIRAL SOLUTES; CHIROPTICAL PROPERTIES; SOLVENT EFFECTS;

CHIRALITY;

SOLVENT;

CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; SHORT SURVEY; STEREOISOMERISM;

COMPUTER SIMULATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SOLVENTS; STEREOISOMERISM;

EID: 35348970443     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702858     Document Type: Short Survey

References (33)

1. L. D. Barron, Molecular Light Scattering and Optical Activity, 2nd ed., Cambridge University Press, Cambridge, 2004.
2. a) P. J. Stephens, J. J. Pan, F. J. Devlin, K. Krohn, T. Kurtán, J. Org. Chem. 2007, 72, 3521-3536;
3. b) T. Mori, Y. Inoue, S. Grimme, J. Phys. Chem. A 2007, 111, 4222-4234;
4. c) M. D. Kundrat, J. Autschbach, J. Phys. Chem. A 2006, 110, 4115-4123;
5. d) A. Glättli, X. Daura, D. Seebach, W. F. van Gunsteren, J. Am. Chem. Soc. 2002, 124, 12972-12978.
6. J. Haesler, I. Schindelholz, E. Riguet, C. G. Bochet, W. Hug, Nature 2007, 446, 526-529.
7. a) G. Zuber, M.-R. Goldsmith, D. N. Beratan, P. Wipf, Chem- PhysChem 2005, 6, 595-597;
8. b) C. Herrmann, K. Ruud, M. Reiher, ChemPhysChem 2006, 7, 2189-2196;
9. c) L. D. Barron, Curr. Opin. Struct. Biol. 2006, 16, 638-643;
10. d) V. Liégeois, O. Quinet, B. Champagne, Int. J. Quantum Chem. 2006, 106, 3097-3107.
11. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Wiley-VCH, Weinheim, 2002.
12. a) M. J. Lowe, J. A. Schellman, J. Mol. Biol. 1972, 65, 91-109;
13. b) H. Goto, E. Yashima, Y. Okamoto, Chirality 2000, 12, 396-399;
14. c) X. Daura, D. Bakowies, D. Seebach, J. Fleischhauer, W. F. van Gunsteren, Eur. Biophys. J. 2003, 32, 661-670.
15. a) L. Jensen, M. Swart, P. T. van Duijnen, J. Autschbach, Int. J. Quantum Chem. 2006, 106, 2479-2488;
16. b) J. Neugebauer, E. J. Baerends, J. Phys. Chem. A 2006, 110, 8786-8796.
17. a) M. P. Allen, D. J. Tildesley, Computer Simulation of Liquids, Oxford University Press, Oxford, 1989;
18. b) W. F. van Gunsteren, D. Bakowies, R. Baron, I. Chandrasekhar, M. Christen, X. Daura, P. Gee, D. P. Geerke, A. Glättli, P. H. Hünenberger, M. A. Kastenholz, C. Oostenbrink, M. Schenk, D. Trzesniak, N. F. A. van der Vegt, H. B. Yu, Angew. Chem. 2006, 118, 4168-4198;
19. Angew. Chem. Int. Ed. 2006, 45, 4064-4092;
20. c) B. Kirchner, Phys. Rep. 2007, 440, 1-111;
21. d) "Ab Initio Molecular Dynamics: Theory and Implementation": D. Marx, J. Hutter in Modern Methods and Algorithms of Quantum Chemistry, Proceedings, NIC Series, Vol. 1 (Ed.: J. Grotendorst), John von Neumann Institute for Computing: Jülich, 2000, pp. 329-477.
22. P. Mukhopadhyay, G. Zuber, P. Wipf, D. N. Beratan, Angew. Chem. 2007, 119, 6570-6572;
23. Angew. Chem. Int. Ed. 2007, 46, 6450-6452.
24. a) K. Ruud, R. Zanasi, Angew. Chem. 2005, 117, 3660-3662;
25. Angew. Chem. Int. Ed. 2005, 44, 3594-3596;
26. b) B. C. Mort, J. Autschbach, J. Phys. Chem. A 2005, 109, 8617-8623;
27. c) J. Kongsted, T. B. Pedersen, M. Strange, A. Osted, A. E. Hansen, K. V. Mikkelsen, F. Pawlowski, P. Jørgensen, C. Hättig, Chem. Phys. Lett. 2005, 401, 385-392.
28. P. Mukhopadhyay, G. Zuber, M.-R. Goldsmith, P. Wipf, D. N. Beratan, ChemPhysChem 2006, 7, 2483-2484.
29. R. Eelkema, B. L. Feringa, Org. Biomol. Chem. 2006, 4, 3729-3745.
30. a) B. Kirchner, J. Hutter, I. F. W. Kuo, C. J. Mundy, Int. J. Mod. Phys. B 2004, 18, 1951-1962;
31. b) B. Kirchner, J. Stubbs, D. Marx, Phys. Rev. Lett. 2002, 89, 215901.
32. J. Fidler, P. M. Rodger, A. Rodger, J. Am. Chem. Soc. 1994, 116, 7266-7273.
33. W. Humphrey, A. Dalke, K. Schulten, J. Molec. Graphics 1996, 14, 33-38.