Information theoretical study of chirality: Enantiomers with one and two asymmetric centra

Journal of Physical Chemistry A

Volumn 112, Issue 42, 2008, Pages 10560-10569

  Janssens, Sara ^a   Borgoo, Alex ^a   Van Alsenoy, Christian ^b   Geerlings, Paul ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^b UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALIGNMENT; ATOMIC PHYSICS; BROMINE; CARBON; CHIRALITY; CHLORINE; ENANTIOMERS; FLUORINE; FUNCTION EVALUATION; HYDROGEN; INFORMATION THEORY; IODINE; OPTICAL PROPERTIES; OPTICAL ROTATION; ORGANIC POLYMERS; STEREOCHEMISTRY;

ARITHMETIC MEANS; ASYMMETRIC CARBONS; CARBON ATOMS; ELECTRON DENSITIES; HALOMETHANES; HIRSHFELD PARTITIONING; LOCAL ENTROPIES; LOCAL INFORMATIONS; MEASURE OF CHIRALITIES; MIXING ENTROPIES; QUANTITATIVE MEASURES; S ENANTIOMERS; SHAPE FUNCTIONS;

ATOMS;

EID: 55649092827     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp711895t     Document Type: Article

References (54)

1. Zabrodsky, H.; Avnir, D. J. Am. Chem. Soc. 1995, 117, 462.
2. Alvarez, S.; Alemany, P.; Avnir, D. Chem. Soc. Rev. 2005, 34, 313, and references cited therein.
3. Petitjean, M. C. R. Acad. Sci. Paris, Chimie/Chemistry 2001, 4, 331.
4. Petitjean, M. Entropy 2003, 5, 271.
5. Carbó, R.; Arnau, M.; Leyda, L. Int. J. Quantum Chem. 1980, 17, 1185.
6. Hodgkin, E. E.; Richards, W. G. Int. J. Quantum Chem. 1987, 14, 105.
7. Rouvray D. H. In Topics in Current Chemistry, Sen, K., Ed.; Springer-Verlag: Berlin Heidelberg, 1995; Vol. 1731, p 1.
8. Parr, R. G.; Yang, W. In Density-Functional Theory of Atoms and Molecules; Oxford University Press; New York, Clarendon Press; Oxford, 1989.
9. Parr, R. G.; Yang, W. Annu. Rev. Phys. Chem. 1995, 46, 701.
10. Chermette, H. J. Comput. Chem. 1999, 20, 129.
11. Geerlings, P.; De Proft, F.; Langenaeker, W. Chem. Rev. 2003, 103, 1793.
12. Geerlings, P.; Boon, G.; Van Alsenoy, C.; De Proft, F. Int. J. Quantum Chem. 2005, 101, 722.
13. Boon, G.; Van Alsenoy, C.; De Proft, F.; Bultinck, P.; Geerlings, P. J. Phys. Chem. A 2003, 107, 11120.
14. Janssens, S.; Van Alsenoy, C.; Geerlings, P. J. Phys. Chem. A 2007, 111, 3143-3151.
15. Janssens, S.; Boon, G.; Geerlings, P. J. Phys. Chem. A 2006, 110, 9267.
16. Boon, G.; De Proft, F.; Langenaeker, W.; Geerlings, P. Chem. Phys. Lett. 1998, 295, 122.
17. Boon, G.; Langenaeker, W.; De Proft, F.; De Winter, H.; Tollenaere, J. P.; Geerlings, P. J. Phys. Chem. A 2001, 105, 8805.
18. Borgoo, A.; Torrent-Sucarrat, M.; De Proft, F.; Geerlings, P. J. Chem. Phys. 2007, 126, 23.
19. Kullback, S.; Leibler, R. A. Ann. Math. Stat. 1951, 22, 79.
20. For a review, see: Gadre, S. In Reviews of Modern Quantum Chemistry; Sen, K. D., Ed.; World Scientific: Singapore, 2002; Vol. 1, p 108.
21. Gadre, S. R.; Kulkarni, S. A.; Shrivastava, I. H. Chem. Phys. Lett. 1990, 166, 445.
22. Gadre, S. R.; Sears, S. B.; Chakravorty, S. J.; Bendale, R. D. Phys. Rev. A 1985, 32, 2602.
23. Nagy, A.; Parr, R. G. Int. J. Quantum Chem. 1996, 58, 323.
24. Nalewajski, R. F.; Parr, R. G. Proc. Natl. Acad. Sci. USA 2000, 97, 8879.
25. Hirshfeld, F. L. Theor. Chim. Acta 1977, 44, 129.
26. Borgoo, A.; Godefroid, M.; Sen, K. D.; De Proft, F.; Geerlings, P. Chem. Phys. Lett. 2004, 399, 363.
27. Borgoo, A.; Godefroid, M.; Indelicate, P.; De Proft, F.; Geerlings, P. J. Chem. Phys. 2007, 126, 44102.
28. De Proft, F.; Geerlings, P. J. Phys. Chem. A 1997, 101, 5344.
29. Ayers, P. W. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 1959.
30. De Proft, F.; Ayers, P. W.; Sen, K. D.; Geerlings, P. J. Chem. Phys. 2004, 120, 9969.
31. Sen, K. D.; De Proft, F.; Borgoo, A.; Geerlings, P. Chem. Phys. Lett. 2005, 410, 70.
32. Shannon, C. E. Bell Syst. Tech. J. 1948, 27, 379.
33. Kullback, S. In Information Theory and Statistics; Wiley: New York, 1959.
34. Parr, R. G.; Bartolotti, L. J. J. Phys. Chem. 1983, 87, 2810.
35. Ayers, P. W.; De Proft, F.; Geerlings, P. Phys. Rev. A 2007, 75, 12508.
36. Mezey, P. G. Mol. Phys. 1999, 96, 169.
37. Parr, R. G.; Ayers, P. W.; Nalewajski, R. F. J. Phys. Chem. A 2005, 109, 3957.
38. Ayers, P. W. Theor. Chem. Acc. 2006, 115, 370.
39. Solà, M.; Mestres, J.; Oliva, J.; Duran, M.; Carbò-Dorca, R. Int. J. Quantum Chem. 1996, 58, 361.
40. Gironés, X.; Robert, D.; Carbó-Dorca, R. J. Comput. Chem. 2001, 22, 255.
41. Constans, P.; Carbó-Dorca, R. J. Chem. Inf. Comput. Sci. 1995, 35, 1046.
42. Constans, P.; Amat, L.; Carbo-Dorca, R. J. Comput. Chem. 1997, 18, 826.
43. Amat, L.; Carbó-Dorca, R. Int. J. Quantum Chem. 2002, 87, 59.
44. Bultinck, P.; Carbó-Dorca, R.; Van Alsenoy, C. J. Chem. Inf. Comput. Sci. 2003, 43, 1208.
45. Bultinck, P.; Kuppens, T.; Gironés, X.; Carbó-Dorca, R. J. Chem. Inf. Comput. Sci. 2003, 43, 1143.
46. Mezey, P. G.; Ponec, R.; Amat, L.; Carbó-Dorca, R. Enantiomer 1999, 4, 371.
47. Boon, G.; Van Alsenoy, C.; De Proft, F.; Bultinck, P.; Geerlings, P. J. Phys. Chem. A 2006, 110, 5114.
48. Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J.; Mennucci, B.; Tomasi, J. Tetrahedron: Asymmetry 2000, 11, 2443.
49. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery,Jr., J. A.; Vreven, T.; Kudin K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A. Gaussian 03, Rev. B.03; Gaussian, Inc.: Pittsburgh PA, 2003.
50. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
51. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
52. Rousseau, B.; Peeters, A.; Van Alsenoy, C. Chem. Phys. Lett. 2000, 324, 189.
53. Van Alsenoy, C.; Peeters, A. J. Mol. Struct. (Theochem) 1993, 105, 19.
54. Meyer, A. Y.; Avnir, D. Struct. Chem. 1991, 2, 475.