Determination of the absolute configuration of pentacoordinate chiral phosphorus compounds in solution by using vibrational circular dichroism spectroscopy and density functional theory

Chemistry - A European Journal

Volumn 16, Issue 8, 2010, Pages 2518-2527

  Yang, Guochun ^a   Xu, Yunjie ^a   Hou, Jianbo ^b   Zhang, Hui ^b   Zhao, Yufen ^b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b XIAMEN UNIVERSITY   (China)

Author keywords

Absolute configuration; Amino acid ligands; Density functional calculations; Isomerization; Vibrational spectroscopy

Indexed keywords

ABSOLUTE CONFIGURATION; C-O STRETCHING REGION; CONFORMATIONAL SEARCH; COORDINATION COMPLEX; DENSITY FUNCTIONAL THEORY CALCULATIONS; DENSITY-FUNCTIONAL CALCULATIONS; DFT CALCULATION; DIASTEREOMERS; HIGH CONFIDENCE; HIGHLY SENSITIVE; PENTACOORDINATE PHOSPHORUS; ROTAMERS; SIDE CHAINS; SPECTROSCOPIC MEASUREMENTS; STEREOGENIC CENTERS; STRUCTURAL INFORMATION; STRUCTURAL VARIATIONS; VIBRATIONAL ABSORPTION; VIBRATIONAL CIRCULAR DICHROISM; VIBRATIONAL CIRCULAR DICHROISM SPECTROSCOPY;

AMINO ACIDS; CHIRALITY; CIRCULAR DICHROISM SPECTROSCOPY; DICHROISM; ELECTRON TRANSITIONS; ENANTIOMERS; ISOMERIZATION; LIGANDS; ONTOLOGY; ORGANIC ACIDS; PHOSPHORUS; PHOSPHORUS COMPOUNDS; PROBABILITY DENSITY FUNCTION; STEREOCHEMISTRY; SULFUR COMPOUNDS; VIBRATIONAL SPECTROSCOPY;

DENSITY FUNCTIONAL THEORY;

COORDINATION COMPOUND; LIGAND; PHOSPHORUS DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; METHODOLOGY; SOLUTION AND SOLUBILITY; SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

CIRCULAR DICHROISM; COORDINATION COMPLEXES; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHOSPHORUS COMPOUNDS; SOLUTIONS; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 77049086390     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902501     Document Type: Article

References (74)

1. (a) K. M. Pietrusiewicz, M. Zabłocka, Chem. Rev. 1994, 94, 1375-1411
2. (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994
3. (c) L. D. Quin, A Guide to Organophosphorus Chemistry, Wiley-Interscience, New York, 2000
4. (d) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000;
5. (e) J. Drabowicz, P. Lyzwa, J. Omelanczuk, K. M. Pietrusiewicz, M. Mikolajczyk, Tetrahedron: Asymmetry 1999, 10, 2757-2763.
6. (a) K.-Y. Akiba, Chemistry of Hypervalent Compounds, Wiley-VCH, New York, 1999
7. (b) R. R. Homes, Pentacoordinated Phosphorus- Structure and Spectroscopy, Vol.I and II, ACS, Washington, 1980
8. (c) D. E. C. Corbridge, Phosphorus: An Outline of Its Chemistry, Biochemistry and Technology, 4th ed., Elsevier, Amsterdam, 1990, Chapter 14, pp. 1233-1256
9. (d) R. Burgada, R. Setton, The Chemistry of Organophosphorus Compounds, Vol.3 (Ed.: F. R. Hartley,), Wiley-Interscience, New York, 1994, pp. 185-277.
10. D. E. C. Corbridge, Phosphorus, Chemistry, Biochemistry and Technology, 4th ed., Elsevier, Amsterdam, 2000.
11. (a) F. H. Westheimer, Acc. Chem. Res. 1968, 1, 70-78
12. (b) S. L. Buchwald, D. H. Pliura, J. R. Knowla, J. Am. Chem. Soc. 1984, 106, 4916-4922
13. (c) J. R. Knowles, Annu. Rev. Biochem. 1980, 49, 877-919
14. (d) P. J. J. M. Vanool, H. M. Buck, Recl. Trav. Chim. Pays-Bas 1984, 103, 119-122
15. (e) R. R. Holmes, Pentacoordinated Phosphorus, Vol.11, ACS, Washington, 1980, p. 87.
16. (a) R. R. Holmes, Acc. Chem. Res. 2004, 37, 746-753
17. (b) R. R. Holmes, Acc. Chem. Res. 1998, 31, 535-542.
18. (a) K. C. K. Swamy, N. S. Kumar, Acc. Chem. Res. 2006, 39, 324-333;
19. (b) N. S. Kumar, K. P. Kumar, K. V. P. P. Kumar, P. Kommana, J. J. Vittal, K. C. K. Swamy, J. Org. Chem. 2004, 69, 1880-1889.
20. N. V. Timosheva, A. Chandrasekaran, R. R. Holmes, J. Am. Chem. Soc. 2005, 127, 12474-12475.
21. H. Fu, J. H. Xu, R. J. Wang, Z. Z. Chen, G. Z. Tu, Q. Z. Wang, Y. F. Zhao, Phosphorus, Sulfur. Silicon. Relat. Elem. 2003, 178, 1963-1971.
22. H. Fu, Z. L. Li, Y. F. Zhao, G. Z. Tu, J. Am. Chem. Soc. 1999, 121, 291-295.
23. (a) S. D. Lahiri, G. F. Zhang, D. Dunaway-Mariano, K. N. Allen, Science 2003, 299, 2067-2071
24. (b) G. M. Blackburn, N. H. Williams, S. J. Gamblin, S. J. Smerdon, Science 2003, 301, 1184c
25. (c) I. Leiros, S. McSweeney, E. Hough, J. Mol. Biol. 2004, 339, 805-820
26. (d) N. H. Williams, Biochim. Biophys. Acta 2004, 1697, 279-287
27. (e) A. C. Hengge, I. Onyido, Curr. Org. Chem. 2005, 9, 61-74
28. (f) W. W. Cleland, A. C. Hengge, Chem. Rev. 2006, 106, 3252-3278
29. (g) A. Wittinghofer, Trends Biochem. Sci. 2006, 31, 20-23
30. (h) I. Catrina, P. J. O'Brien, J. Purcell, I. Nikolic-Hughes, J. G. Zalatan, A. C. Hengge, D. Herschlag, J. Am. Chem. Soc. 2007, 129, 5760-5765
31. (i) E. Marcos, R. Crehuet, J. M. Anglada, J. Chem. Theory Comput. 2008, 4, 49-63.
32. (a) H. Fu, G. Z. Tu, Z. L. Li, Y. F. Zhao, R. Q. Zhang, J. Chem. Soc. Perkin Trans. 1997, 2021-2022
33. (b) L. Yu, Z. Liu, H. Fang, Q. L. Zeng, Y. F. Zhao, Amino Acids 2005, 28, 369-372.
34. J. B. Hou G. Tang, J. N. Guo, Y. Liu, H. Zhang, Y. F. Zhao, Tetrahedron: Asymmetry 2009, 20, 1301-1307.
35. (a) T. A. Keiderling, Nature 1986, 322, 851-852
36. (b) K. Nakanishi, N. Berova, R. W. Woody, Circular Dichroism: Principles and Applications, Wiley-VCH, Weinheim, 2000
37. (c) R. A. G. D. Silva, J. Kubelka, P. Bour, S. M. Decatur, T. A. Keiderling, Proc. Natl. Acad. Sci. USA 2000, 97, 8318-8323;
38. (d) J. H. Choi, M. Cho, J. Chem. Phys. 2004, 120, 4383-4392
39. (e) G. Shanmugam, P. L. Polavarapu, J. Am. Chem. Soc. 2004, 126, 10292-10295
40. (f) J. Hilario, J. Kubelka, T. A. Keiderling, J. Am. Chem. Soc. 2003, 125, 7562-7574
41. (g) F. Eker, X. L. Cao, L. Nafie, R. Schweitzer-Stenner, J. Am. Chem. Soc. 2002, 124, 14330-14341.
42. (a) L. D. Barron, Molecular Light Scattering and Optical Activity, 2nd ed., Cambridge University Press, New York, 2004
43. (b) T. Brotin, D. Cavagnat, J. P. Dutasta, T. Buffeteau, J. Am. Chem. Soc. 2006, 128, 5533-5540
44. (c) P. J. Stephens, J. J. Pan, K. Krohn, J. Org. Chem. 2007, 72, 7641-7649
45. (d) A. Muranaka, M. Shibahara, M. Watanabe, T. Matsumoto, T. Shinmyozu, N. Kobayashi, J. Org. Chem. 2008, 73, 9125-9128
46. (e) H. Izumi, A. Ogata, L. A. Nafie, R. K. Dukor, J. Org. Chem. 2009, 74, 1231-1236
47. (f) G. Tarczay, G. Magyarfalvi, E. Vass, Angew. Chem. 2006, 118, 1807-1809
48. Angew. Chem. Int. Ed. 2006, 45, 1775-1777;
49. g) M. Urbanová, V. Setnicka, F. J. Devlin, P. J. Stephens, J. Am. Chem. Soc. 2005, 127, 6700-6711
50. (h) K. Monde, T. Taniguchi, N. Miura, J. Am. Chem. Soc. 2004, 126, 9496-9497.
51. (a) S. G. Stepanian, I. D. Reva, E. D. Radchenko, L. Adamowicz, J. Phys. Chem. A 1999, 103, 4404-4412
52. (b) S. Mondal, D. S. Chowdhuri, S. A. Ghosh, S. Dalai, THEOCHEM 2007, 810, 81-89
53. (c) R. Jacob, G. Fischer, J. Phys. Chem. A 2003, 107, 6136-6143.
54. (a) R. Schweitzer-Stenner, Vib. Spectrosc. 2006, 42, 98-117
55. b) R. Schweitzer-Stenner, F. Eker, K. Griebenow, X. L. Cao, L. A. Nafie, J. Am. Chem. Soc. 2004, 126, 2768-2776.
56. a) H. Nakazawa, K. Kawamura, T. Ogawa, K. Miyoshi, J. Organomet. Chem. 2002, 646, 204-211
57. b) S. Kojima, K. Kajiyama, M. Nakamoto, S. Matsukawa, K. Akiba, Eur. J. Org. Chem. 2006, 218-234.
58. a) J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094
59. b) C. Cramer, D. Truhlar, Chem. Rev. 1999, 99, 2161-2200.
60. E. J. Cocinero, A. Lesarri, J. U. Grabow, J. C. Lopez, J. L. Alonso, ChemPhysChem 2007, 8, 599-604.
61. Gaussian 03, Revision B.05, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, Gaussian, Inc., Wallingford, CT, 2003.
62. (a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652
63. (b) C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B-Condens. Matter Mater. Phys. 1988, 37, 785-789.
64. (a) P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627
65. (b) T. Brotin, D. Cavagnat, J.-P. Dutasta, T. Buffeteau, J. Am. Chem. Soc. 2006, 128, 5533 -5540;
66. (c) T. A. Martinek, I. M. Mándity, L. Fülcöp, G. K. Tóth, E. Vass, M. Holló, E. Forró, F. Fülcl;p, J. Am. Chem. Soc. 2006, 128, 13539-13544
67. (d) D. Cavagnat, L. Lespade, T. Buffeteau, J. Phys. Chem. A 2007, 111, 7014-7021
68. (e) H. Izumi, A. Ogata, L. A. Nafie, R. K. Dukor, J. Org. Chem. 2009, 74, 1231-1236
69. (f) T. B. Freedman, X. L. Ca, Z. Luz, H. Zimmermann, R. Poupko, L. A. Nafie, Chirality 2008, 20, 673-680.
70. (a) E. Debie, P. Bultinck, W. Herrebout, B. van der Veken, Phys. Chem. Chem. Phys. 2008, 10, 3498-3508
71. (b) J. T. He, A. G. Petrovic, P. L. Polavarapu, J. Phys. Chem. B 2004, 108, 20451-20457
72. (c) J. T. He, A. Petrovich, P. L. Polavarapu, J. Phys. Chem. A 2004, 108, 1671-1680
73. (d) K. K. Lee, K. I. Oh, H. Lee, C. Joo, H. Han, M. Cho, ChemPhysChem 2007, 8, 2218-2226.
74. E. Cancés, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032-3041.