P(=O)H to P-OH Tautomerism: A Theoretical and Experimental Study

Journal of Organic Chemistry

Volumn 80, Issue 20, 2015, Pages 10025-10032

  Janesko, Benjamin G ^a   Fisher, Henry C ^a   Bridle, Mark J ^a   Montchamp, Jean Luc ^a  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; PHOSPHORUS DERIVATIVE;

ARTICLE; INVESTIGATIVE PROCEDURES; PREDICTION; QUANTITATIVE STUDY; TAUTOMER; TAUTOMERIZATION; THEORETICAL STUDY; THERMODYNAMICS; VALIDATION STUDY;

EID: 84944937248     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01618     Document Type: Article

References (79)

1. Hartley, F. R. The Chemistry of Organophosphorus Compounds; Wiley: New York, 1996; Vol. 4.
2. Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000.
3. Flett, D. S. J. Organomet. Chem. 2005, 690, 2426-2438 10.1016/j.jorganchem.2004.11.037
4. Savignac, P.; Iorga, B. Modern Phosphonate Chemistry; CRC: Boca Raton, FL, 2003.
5. Corbridge, D. E. C. Phosphorus: An Outline of Its Chemistry, Biochemistry and Uses, 5 th ed.; Elsevier: Amsterdam, 1995.
6. Büchel, K. H.; Moretto, H.-H.; Woditsch, P. Industrial Inorganic Chemistry, 2 nd ed.; Wiley-VCH: New York, 2000; pp 65-101.
7. Kirk-Othmer Encyclopedia of Chemical Technology, 4 th ed.; Wiley: New York, 1999; Vol. 18.
8. Nifant'ev, E. E. Russ. Chem. Rev. 1978, 47, 835-858 10.1070/RC1978v047n09ABEH002278
9. Fletcher, J. H.; Dermer, O. C.; Fox, R. B. Adv. Chem. Ser. 1974, 126, 278-288 10.1021/ba-1974-0126.ch036
10. Guthrie, J. P. Can. J. Chem. 1979, 57, 236-239 10.1139/v79-039
11. Hammond, P. R. J. Chem. Soc. 1962, 1365 10.1039/jr9620001365
12. Mehrotra, R. N. Eur. Chem. Bull. 2013, 2, 758-776
13. Christiansen, A.; Selent, D.; Spannenberg, A.; Köckerling, M.; Reinke, H.; Baumann, W.; Jiao, H.; Franke, R.; Börner, A. Chem.-Eur. J. 2011, 17, 2120-2129 10.1002/chem.201002823
14. Algarra, A. G.; Fernández-Trujillo, M. J.; Hernández-Molina, R.; Basallote, M. G. Dalton Trans. 2011, 40, 8589-8597 10.1039/c1dt10625b
15. Jung, L.-Y.; Tsai, S.-H.; Hong, F.-E. Organometallics 2009, 28, 6044-6053 10.1021/om900435y
16. Akbayeva, D. N.; Di Vaira, M.; Constantini, S. S.; Peruzzini, M.; Stoppioni, P. Dalton Trans. 2006, 389-395 10.1039/B510479C
17. Sokolov, M. N.; Chubarova, E. V.; Kovalenko, K. A.; Mironov, I. V.; Virovets, A. V.; Peresypkina, E. V.; Fedin, V. P. Russ. Chem. Bull. 2005, 54, 615-622 10.1007/s11172-005-0296-1
18. Sharma, P. K. Indian J. Chem. 2002, 41A, 1612-1615
19. Chandra, S. K.; Gelerinter, E.; Gould, E. S. Inorg. Chem. 1995, 34, 4057-4061 10.1021/ic00120a008
20. Seth, M.; Mathur, A.; Banerji, K. K. Bull. Chem. Soc. Jpn. 1990, 63, 3640-3643 10.1246/bcsj.63.3640
21. Sernaglia, R. L.; Franco, D. W. Inorg. Chem. 1989, 28, 3485-3489 10.1021/ic00317a018
22. Gallagher, M. J.; Honegger, H. Tetrahedron Lett. 1977, 18, 2987-2990 10.1016/S0040-4039(01)83134-8
23. Bailey, W. J.; Fox, R. B. J. Org. Chem. 1964, 29, 1013-1017 10.1021/jo01028a007
24. Bailey, W. J.; Fox, R. B. J. Org. Chem. 1963, 28, 531-534 10.1021/jo01037a069
25. Cherbuliez, E.; Weber, G.; Rabinowitz, J. Helv. Chim. Acta 1963, 46, 2464-2470 10.1002/hlca.19630460669
26. Griffiths, J. E.; Burg, A. B. J. Am. Chem. Soc. 1960, 82, 1507-1508 10.1021/ja01491a062
27. Hoge, B.; Neufeind, S.; Hettel, S.; Wiebe, W.; Thösen, C. J. Organomet. Chem. 2005, 690, 2382-2387 10.1016/j.jorganchem.2004.09.041
28. Kurscheid, B.; Wiebe, W.; Neumann, B.; Stammler, H.-G.; Hoge, B. Eur. J. Inorg. Chem. 2011, 2011, 5523-5529 10.1002/ejic.201100984
29. Wesolowski, S. S.; Brinkmann, N. R.; Valeev, E. F.; Schaefer, H. F.; Repasky, M. P.; Jorgensen, W. L. J. Chem. Phys. 2002, 116, 112 10.1063/1.1418440
30. Springs, B.; Haake, P. J. Org. Chem. 1977, 42, 472-474 10.1021/jo00423a017
31. Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. Org. Lett. 2005, 7, 2583-2585 10.1021/ol050695e
32. Pettersen, D.; Marcolini, M.; Bernardi, L.; Fini, F.; Herrera, R. P.; Sgarzani, V.; Ricci, A. J. Org. Chem. 2006, 71, 6269-6272 10.1021/jo060708h
33. Abrunhosa-Thomas, I.; Ribière, P.; Adcock, A. C.; Montchamp, J.-L. Synthesis 2006, 325-331 10.1055/s-2005-924768
34. Gavara, L.; Petit, C.; Montchamp, J.-L. Tetrahedron Lett. 2012, 53, 5000-5003 10.1016/j.tetlet.2012.07.019
35. Kraihanzel, C. S.; Bartish, C. M. J. Am. Chem. Soc. 1972, 94, 3572-3575 10.1021/ja00765a052
36. Yakhvarov, D.; Caporali, M.; Gonsalvi, L.; Latypov, S.; Mirabello, V.; Rizvanov, I.; Sinyashin, O.; Stoppioni, P.; Peruzzini, M. Angew. Chem., Int. Ed. 2011, 50, 5370-5373 10.1002/anie.201100822
37. Manca, G.; Caporali, M.; Ienco, A.; Peruzzini, M.; Mealli, C. J. Organomet. Chem. 2014, 760, 177-185 10.1016/j.jorganchem.2013.10.043
38. Belabassi, Y.; Antczak, M. I.; Tellez, J.; Montchamp, J.-L. Tetrahedron 2008, 64, 9181-9190 10.1016/j.tet.2008.07.054
39. Montchamp, J.-L. Acc. Chem. Res. 2014, 47, 77-87 10.1021/ar400071v
40. Montchamp, J.-L. Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 66-75 10.1080/10426507.2012.727925
41. Han, L.-B.; Zhao, C.-Q.; Onozawa, S.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843 10.1021/ja025816+
42. Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080-5081 10.1021/ja0494297
43. Petit, C.; Fécourt, F.; Montchamp, J.-L. Adv. Synth. Catal. 2011, 353, 1883-1888 10.1002/adsc.201100361
44. Chesnut, D. B. Heteroat. Chem. 2000, 11, 73-80 10.1002/(SICI)1098-1071(2000)11:1<73::AID-HC11>3.0.CO;2-#
45. Boatz, J. A.; Schmidt, M. W.; Gordon, M. S. J. Phys. Chem. 1987, 91, 1743-1749 10.1021/j100291a014
46. Babin, Y. V.; Prisyazhnyuk, A. V.; Ustynyuk, Y. A. Russ. J. Phys. Chem. A 2008, 82, 94-100 10.1134/S0036024408010147
47. Prisyazhnyuk, A. V.; Babin, Y. V. J. Struct. Chem. 2005, 46, 164-167 10.1007/s10947-006-0024-2
48. Mamaev, V. M.; Prisyajnuk, A. V.; Laikov, D. N.; Logutenko, L. S.; Babin, Y. V. Mendeleev Commun. 1999, 9, 240-241 10.1070/MC1999v009n06ABEH001095
49. Cho, B.; Tan, C.-H.; Wong, M. W. Org. Biomol. Chem. 2011, 9, 4550-4557 10.1039/c1ob05186e
50. Babin, Y. V.; Ustynyuk, Y. A. Russ. J. Phys. Chem. A 2007, 81, 1810-1819 10.1134/S0036024407110167
51. Ustynyuk, Yu. A.; Babin, Yu. V. Russ. J. Gen. Chem. 2008, 78, 822-832 10.1134/S1070363208040415
52. Deprèle, S.; Montchamp, J.-L. J. Org. Chem. 2001, 66, 6745-6755 10.1021/jo015876i
53. Deprèle, S.; Montchamp, J.-L. J. Organomet. Chem. 2002, 643-644, 154-163 10.1016/S0022-328X(01)01204-9
54. Deprèle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386-9387 10.1021/ja0261978
55. Deprèle, S.; Montchamp, J.-L. Org. Lett. 2004, 6, 3805-3808 10.1021/ol0484198
56. Ribière, P.; Bravo-Altamirano, K.; Antczak, M. I.; Hawkins, J. D.; Montchamp, J.-L. J. Org. Chem. 2005, 70, 4064-4072 10.1021/jo050096l
57. Fisher, H. C.; Prost, L.; Montchamp, J.-L. Eur. J. Org. Chem. 2013, 2013, 7973-7978 10.1002/ejoc.201301412
58. Goerigk, L.; Grimme, S. Phys. Chem. Chem. Phys. 2011, 13, 6670-6688 10.1039/c0cp02984j
59. Becke, A. D. J. Chem. Phys. 2014, 140, 18A301-18A301 10.1063/1.4869598
60. Cramer, C. J.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 760-768 10.1021/ar800019z
61. Hratchian, H. P.; Schlegel, H. B. J. Chem. Phys. 2004, 120, 9918-9924 10.1063/1.1724823
62. Busacca, C. A.; Lorenz, J. C.; Grinberg, N.; Haddad, N.; Hrapchak, M.; Latli, B.; Lee, H.; Sabila, P.; Saha, A.; Sarvestani, M.; Shen, S.; Varsolona, R.; Wei, X.; Senanayake, C. H. Org. Lett. 2005, 7, 4277-4280 10.1021/ol0517832
63. Maffei, M.; Buono, G. Tetrahedron 2003, 59, 8821-8825 10.1016/j.tet.2003.08.067
64. Dumond, Y.; Baker, R.; Montchamp, J. Org. Lett. 2000, 2, 3341-3344 10.1021/ol006434g
65. McKenna, C. E. (The University of Southern California). Improved Preparations of Thiophosphites and Thiophosphonates. US Patent 6,284,909, Sept 4, 2001.
66. Ortial, S.; Fisher, H. C.; Montchamp, J.-L. J. Org. Chem. 2013, 78, 6599-6608 10.1021/jo4008749
67. Gatrone, R. C.; Kaplan, L.; Philip Horwitz, E. Solvent Extr. Ion Exch. 1987, 5, 1075-1116 10.1080/07366298708918611
68. Shioji, K.; Matsumoto, A.; Takao, M.; Kurauchi, Y.; Shigetomi, T.; Yokomori, Y.; Okuma, K. Bull. Chem. Soc. Jpn. 2007, 80, 743-746 10.1246/bcsj.80.743
69. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Ö. Farkas; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
70. Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864 10.1103/PhysRev.136.B864
71. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133
72. Becke, A. D. J. Chem. Phys. 1993, 98, 5648 10.1063/1.464913
73. Stephens, P.; Devlin, F.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627 10.1021/j100096a001
74. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261 10.1063/1.1677527
75. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007 10.1063/1.456153
76. Dunning, T. H. J. Phys. Chem. A 2000, 104, 9062-9080 10.1021/jp001507z
77. Dunning, T. H.; Peterson, K. A.; Wilson, A. K. J. Chem. Phys. 2001, 114, 9244-9253 10.1063/1.1367373
78. Feller, D. J. Comput. Chem. 1996, 17, 1571-1586 10.1002/(SICI)1096-987X(199610)17:13<1571::AID-JCC9>3.0.CO;2-P
79. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396 10.1021/jp810292n