The mechanism of nucleophilic displacements at phosphorus in chloro-substituted methylphosphonate esters: P-O vs P-C bond cleavage: A DFT study

Journal of Organic Chemistry

Volumn 75, Issue 6, 2010, Pages 1917-1926

  Ashkenazi, Nissan ^a   Segall, Yoffi ^a   Chen, Ravit ^a   Sod Moriah, Gali ^a   Fattal, Eyal ^a  

^a ISRAEL INSTITUTE FOR BIOLOGICAL RESEARCH   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACID DERIVATIVE; BOND DISSOCIATION; CHEMICAL EQUATIONS; CHLORINE ATOM; CHLOROMETHYL; DFT STUDY; DIMETHYL METHYLPHOSPHONATE; METHYL LIGANDS; NUCLEOPHILIC DISPLACEMENT; P-C BOND CLEAVAGE; P-O BONDS; PHOSPHONATES; SEQUENTIAL ADDITION; SOLVENT EFFECTS; TRANSITION STATE;

CHEMICAL REACTIONS; CHLORINE; ESTERS; PHOSPHORUS; QUANTUM CHEMISTRY;

CHEMICAL BONDS;

DIMETHYL CHLOROMETHYLPHOSPHONATE DERIVATIVE; DIMETHYL DICHLOROMETHYLPHOSPHONATE DERIVATIVE; DIMETHYL METHYLPHOSPHONATE DERIVATIVE; DIMETHYL TRICHLOROMETHYLPHOSPHONATE DERIVATIVE; ESTER DERIVATIVE; METHYLPHOSPHONATE ESTER DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DISSOCIATION; ELECTRIC POTENTIAL; ISOELECTRIC FOCUSING; SOLVENT EFFECT; SURFACE PROPERTY; SYNTHESIS;

CARBON; CHLORINE; COMPUTER SIMULATION; ESTERS; MODELS, MOLECULAR; ORGANOPHOSPHORUS COMPOUNDS; OXYGEN; PHOSPHORUS; QUANTUM THEORY;

EID: 77949833531     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9026325     Document Type: Article

References (96)

1. (a) Engel, R. Synthesis of Carbon-Phosphorus Bonds; CRC Press: Boca Raton, FL, 1988.
2. (b) The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: Chichester, UK, 1996; Vol. 4.
3. (c) A Guide to Organophosphorus Chemistry; Quin, L. D., Ed.; Wiley-Interscience: New York, 2000.
4. (d) Mikolajczyk, M.; Balczewski, P. Top. Curr. Chem. 2003, 223, 161.
5. Alkyl phosphonates are known toreaStascarbanions only with carbonyl compounds in the Horncr-Wadsworth-Emmons reaction, via a different mechanism (nucleophilic attack of phosphoryl-stabilized carbanion on carbonylic carbon), see: Ando K. J. Org. Chem. 1999, 64, 6815 and ref 8 therein. This reaction is normally feasible only for activated alkylphosphonates.
6. See: Maryanoff, B. E.; Raitz, A. B. Chem. Rev. 1989, 89, 863.
7. (a) Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70.
8. (b) Gillespie, P.; Hoffman, P.; Klusack, H.; Marquarding, D.; Pfohl, S.; Ramirez, F.; Ugi, I. Angew. Chem. Int. Ed. 1971, 10, 687.
9. (c) Gillespie, P.; Ramirez, F.; Ugi, I.; Marquarding, D. Angew. Chem. Int. Ed. 1973, 12, 91.
10. (d) Hoffman, R.; Howell, J. M.; Muetterties, E. L. J. Am. Chem. Soc. 1972, 94, 3047.
11. Leyssens, T.; Peeters, D. J. Org. Chem. 2008, 73, 2725 and references cited therein.
12. (a) Paul, R. M. J. Chem. Soc. 1955, 574.
13. (b) Burg, A. B.; Sarkis, A. J. J. Am. Chem. Soc. 1965, 87, 238.
14. Hall, C. R.; Inch, T. D.; Peacock, G.; Pottage, C.; Williams, N. E. J. Chem. Soc. Perkin Trans. 1 1984, 669.
15. Hammond, P. S.; Kircnner, M. B.; Lieske, C. N. J. Org. Chem. 1990, 55, 6049.
16. (a) Hammerschmidt, F. Monatsh. Chem. 1993, 124, 1063.
17. (b) Hammerschmidt, F.; Schmidt, S. Eur. J. Org. Chem. 2000, 2239.
18. Hawkins, M. J.; Powell, E. T.; Leo, G. C.; Gauthier, D. A.; Greco, M. N.; Marynoff, B. Org. Lett. 2006, 8, 3429.
19. (a) Berry, J. P.; Arnold, J. R.; Isbell, A. F. J. Org. Chem. 1968, 33, 1664.
20. (b) Perlikowska, W.; Modro, A. M.; Modro, T. A.; Mphahlele, M. J. J. Chem. Soc., Perkin Trans. 21996, 2661.
21. (c) Zafrani, Y.; Sod-Moriah, G.; Segall, Y. Tetrahedron 2009, 65, 5278.
22. (a) Segall, Y.; Toia, R. F.; Casida, J. E. Phosphorus. Sulfur Silicon Relat. Elem. 1993, 75, 191.
23. (b) Segall, Y.; Grendell, R. L.; Toia, R. F.; Casida, J. E. J. Agric. Food Chem. 1991, 39, 380.
24. For earlier reviews see: (a) Yang, Y.-C.; Baker, J. A.; Ward, R. Chem. Rev. 1992, 92, 1729.
25. (b) Yang, Y.-C. Acc. Chem. Res. 1999, 32, 109. For more recent review see:
26. (c) Smith, B. M. Chem. Soc. Rev. 2008, 37, 470. For other citations see:
27. (d) Bhattacharya, S.; Snehalatha, K. J. Org. Chem. 1997, 62, 2198.
28. (e) Bhattacharya, S.; Snehalatha, K.; George. S. K. J. Org. Chem. 1998, 63, 27.
29. (f) Bhattacharya, S.; Snehalatha, K.; Vemula, P. K. J. Org. Chem. 2003, 68, 2741.
30. (g) Bhattacharya, S.; Vemula, P. K. J. Org. Chem. 2004, 69, 559.
31. (h) Bhattacharya, S.; Vemula, P. K. Langmuir 2005, 21, 71.
32. (i) Wagner, G. W.; Koper, O. B.; Lucas, E.; Decker, S.; Klabunde, K. J. J. Phys. Chem. B 2000, 104, 5118.
33. (j) Wagner, G. W.; Bartram, P. W.; Koper, O. B.; Klabunde, K. J. J. Phys. Chem. B 1999, 103, 3225.
34. (k) Wagner, G. W.; Bartram, P. W. Langmuir 1999, 15, 8113.
35. Wagner, G. W.; Procell, L. R.; O'Connor, R. J.; Munavalli, S.; Carnes, C. L.; Kapoor, P. N.; Klabunde, K. J. J. Am. Chem. Soc. 2001, 123, 1636.
36. (m) Wagner, G. W.; Procell, L. R.; Munavalli, S. J. Phys. Chem. C 2007, 111, 17564.
37. (n) Wagner, G. W.; Chen, Q.; Wu, Y. J. J. Phys. Chem. Chem. C 2008, 112, 11901.
38. (o) Gershonov, E.; Columbus, I.; Zafrani, Y. J. Org. Chem. 2009, 74, 329.
39. 3 bond is cleaved more readily than the P-SMe bond (see ref 6) and P-O-p-nitrophenyl bond (see ref 7).
40. Examples for phosphates: (a) Dejaegere, A.; Karplus, M. J. Am. Chem. Soc. 1993, 115, 5316.
41. (b) Dejaegere, A.; Liang, X.; Karplus, M. J. Chem. Soc. Faraday Trans. 1994, 90, 1763.
42. (c) Chang, N.-Y.; Lim, C. J. Phys. Chem. A 1997, 101, 8706.
43. (d) Chang, N.-Y.; Lim, C. J. Am. Chem. Soc. 1998, 120, 2156.
44. (e) Florian, J.; Warshel, A. J. Phys. Chem. B1998, 102, 719.
45. (f) Hu, C.-H.; Brinck, T. J. Phys. Chem. A 1999, 103, 5379.
46. (g) Lopez, X.; Dejaegere, A.; Karplus, M. J. Am. Chem. Soc. 2001, 123, 11755.
47. (h) Menegon, G.; Loos, M.; Chaimovich. H. J. Phys. Chem. A 2002, 106, 9078.
48. (i) Arantes, G. M.; Chaimovich, H. J. Phys. Chem. A 2005, 109, 5625.
49. (j) López, C. S.; Faza, O. N.; de Lera, A. R.; York, D. M. Chem.-Eur. J. 2005, 11, 2081.
50. (k) Iché-Tarrat, N.; Barthelat, J.-C.; Rinaldi, D.; Vigroux, A. J. Phys. Chem. B 2005, 109, 22570.
51. (l) Lopez, X.; Dejaegere, A.; Leclerc, F.; York, D. M.; Karplus, M. J. Phys. Chem. B 2006, 110, 11525.
52. Examples for phosphonates: (a) Thatcher, G. R. J.; Campbell, A. S. J. Org. Chem. 1993, 58, 2272.
53. (b) Patterson, E. V.; Cramer, C. J. J. Phys. Org. Chem. 1998, 11, 232.
54. (c) Zheng, F.; Zhan, C-G.; Ornstein, R. L. J. Chem. Soc., Perkin Trans. 2 2001, 2355.
55. (d) Bell, A. J.; Citra, A.; Dyke, J. M.; Ferrante, F.; Gagliardi, L.; Watts, P. Phys. Chem. Chem. Phys. 2004, 6, 1213.
56. (e) Barbosa, A. C. P.; Borges, I., Jr.; Lin, W. O. J. Mol. Struct. (THEOCHEM) 2004, 712, 187.
57. (f) Sečkutė J.; Menke, J. L.; Emnett, R. J.; Patterson, E. V.;Cramer,C. J. J. Org. Chem. 2005, 70, 8649.
58. (g) Doskocz, M.; Roszak, S.; Majumbar, D.; Doskocz, J.; Gancarz, R.; Leszczynski, J. J. Phys. Chem. A 2008, 112, 2077.
59. (h) Daniel, K. A.; Kopff, L. A.; Patterson, E. V. J Phys. Crg. Chem. 2008, 21, 321.
60. (i) McAnoy, A. M.; Paine, M. R. L.; Blanksby, S. J. Org. Biomol. Chem. 2008, 6, 2316.
61. (j) McAnoy, A. M.; Williams, J.; Paine, M. R. L.; Rogers, M. L.; Blanksby, S. J. Org. Chem. 2009, 74, 9319.
62. See: Edmundson, R. S. in ref lb, Chapter 6 , pp 496-652.
63. (a) Hodges, R. V.; Sullivan, S. A.; Beauchamp, J. L . J. Am. Chem. Soc. 1980, 102, 935.
64. (b) Lum, R. C.; Grabowski, J. J. J. Am. Chem. Soc. 1992, 114, 8619.
65. (a) Ashkenazi, N.; Zade, S. S.; Segall, Y.; Karton, Y.; Bendikov, M. Chem. Commun. 2005, 5879.
66. (b) Ashkenazi, N.; Segall, Y.; Karton, Y.; Zade, S. S.; Bendikov, M. Phosphorous. Sulfur. Silicon Relat. Elem. 2008, 183, 420.
67. (a) Haake, P. C.; Westheimer, F. H. J. Am. Chem. Soc. 1961, 83, 1102.
68. (b) Kluger, R.; Covitz, F.; Dennis, E.; Williams, L. W.; Westheimer, F. H. J. Am. Chem, Soc. 1969, 91, 6066.
69. (c)Kluger, R.; Thatcher, G. R. J. Am. Chem. Soc. 1985, 107, 6006.
70. (d) Kluger, R.; Thatcher, G. R. J. Org. Chem. 1986, 51, 207.
71. (e) Yang, Y.-C. Acc. Chem. lies. 1999, 32, 109.
72. Bunion, C. A. Acc. Chem. Res. 1970, 3, 257.
73. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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.; Klene, 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.; Parkas, 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.; Pople, J. A. Gaussian 03, Revision D.01; Gaussian, Inc., Wallingford, CT, 2004.
74. (a) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem, phys. Lett. 1996, 255, 327 and references cited therein.
75. (b) Cances, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
76. See the discussion in: (a) Vemula, P. K.; Ganguly, B.; Bhattacharya, S. J. Org. Chem. 2004, 69, 8634.
77. (b) Bhattacharya, S.; Vemula, P. K. J. Org. Chem. 2005, 70, 9677.
78. Barnard, P. W. C.; Bunton, C. A.; Llewellyn, D. R.; Vernon, C. A.; Welch, V. A. J. Chem. Soc. 1961, 2670.
79. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
80. (a) Aksnes, G.; Songstad, J. Acta Chem. Scand. 1965, 19, 893.
81. (b) Aksnes, G.; Gierstae, R.; Wulvik, E. A. Phaspharus Sulfur Relat. Elem. 1988, 39, 141.
82. -.
83. Bone, S. A.; Trippett, S.; Whittle, P. J. J. Chem. Soc., Perkin Trans. 1 1977, 437.
84. (a) For a review see: Eymery, F.; Iorga, B.; Savignac, P. Tetrahedron 1999, 55, 13109.
85. (b) Ashkenazi, N.; Karton, Y.; Segall, Y. Tetrahedron Lett. 2004, 45, 8003.
86. Frank, A. W. Can. J. Chem. 1968, 46, 3573.
87. By increasing the elecetronegativity and/or the steric bulk of the ligand. See: (a) Trippett, S. Pure Appl. Chem. 1974, 40, 595.
88. (b) Trippett, S. Phosphorus Sulfur Relat. Elem. 1976, 1, 89.
89. (a) van Bochove, M. A.; Swart, M.; Bickelhaupt, F. M. J. Am. Chem. Soc. 2006, 128, 10738.
90. (b) van Bochove, M. A.; Swart, M.; Bickelhaupt, F. M. Chem Phys Chem 2007, 8, 2452.
91. (c) van Bochove, M. A.; Bickelhaupt, F. M. Eur. J. Org. Chem. 2008, 649.
92. Zueco, C.; Lima, C. F.; Rezende, M. C.; Vianna, J. F.; Nome, F. J. Org. Chem. 1987, 52, 5356.
93. (a) Nome, F.; Schwingel, E. W.; Ionesco, L. G. J. Org. Chem.-1980, 45, 705.
94. (b) Nome, F.; Erbs, W.; Correia, V. R. J. Org. Chem. 1981, 46, 3802.
95. Fedoryński, M. Chem. Rev. 2003, 103, 1099.
96. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, Version 3.1, Theoretical Chemistry Institute, University of Wisconsin, Madison WI, 2001.