Trans and Cis influences in hypervalent iodine(III) complexes: A DFT study

Inorganic Chemistry

Volumn 52, Issue 10, 2013, Pages 6046-6054

  Sajith, P K ^a   Suresh, Cherumuttathu H ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

IODINATED HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; STEREOISOMERISM;

HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM;

EID: 84877979853     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic400399v     Document Type: Article

References (73)

1. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997.
2. Stang, P. J. J. Org. Chem. 2003, 68, 2997
3. Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123
4. Moriarty, R. M.; Prakash, O. Hypervalent Iodine in Organic Chemistry: Chemical Transformations; Wiley-Interscience: New York, 2008.
5. Ochiai, M. Chemistry of Hypervalent Compounds; Wiley-VCH: New York, 1999.
6. Ochiai, M. Chem. Rec. 2007, 7, 12
7. Richardson, R. D.; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402
8. Zhdankin, V. V. Curr. Org. Synth. 2005, 2, 121
9. Wirth, T. Hypervalent Iodine Chemistry; Topics in Current Chemistry; Springer: Berlin, 2003; Vol. 224.
10. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299
11. Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052
12. Uyanik, M.; Akakura, M.; Ishihara, K. J. Am. Chem. Soc. 2009, 131, 251
13. Ochiai, M. Top. Curr. Chem. 2003, 224, 5
14. Paintner, F. F.; Allmendinger, L.; Bauschke, G. Synthesis 2001, 2113
15. Zhdankin, V. V. ARKIVOC 2009, 1
16. Thoma, H.; Kita, Y. Adv. Synth. Catal. 2004, 346, 111
17. Zhdankin, V. V.; Stang, P. J. J. Chem. Rev. 2002, 102, 2523
18. Deprezand, N. R.; Sanford, M. S. Inorg. Chem. 2007, 46, 1924
19. Phippsand, R. J.; Gaunt, M. J. Science 2009, 323, 1593
20. Brand, J. P.; Gonzalez, D. F.; Nicolai, S.; Waser, J. Chem. Commun. 2011, 47, 102
21. Souto, J. A.; Zian, D.; Muniz, K. J. Am. Chem. Soc. 2012, 134, 7242
22. Musher, J. I. Angew. Chem., Int. Ed. 1969, 8, 54
23. Reed, R. E.; von Rague Schleyer, P. J. Am. Chem. Soc. 1990, 112, 1434
24. Kutzelnigg, W. Angew. Chem., Int. Ed. 1984, 23, 272
25. Weinhold, F.; Landis, C. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: New York, 2005.
26. Silva, L. F., Jr.; Olofssonb, B. Nat. Prod. Rep. 2011, 28, 1722
27. Koser, G. F.; Relenyi, A. G.; Kalos, A. N.; Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1982, 47, 2487
28. Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656
29. Norrby, P.-O.; Petersen, T. B.; Bielawski, M.; Olofsson, B. Chem.-Eur. J. 2010, 16, 8251
30. Ghosh, H.; Baneerjee, A.; Rout, S. K.; Patel, B. K. ARKIVOC 2011, 209
31. Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052
32. Martin, J. C.; Perozzi, E. F. Science 1976, 191, 154
33. Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410
34. Kiprof, K.; Zhdankin, V. ARKIVOC 2003, 170
35. Koser, G. F.; Sun, G.; Porter, C. W.; Youngs, W. J. J. Org. Chem. 1993, 58, 7310
36. Niedermann, K.; Welch, J. M.; Koller, R.; Cvengros, J.; Santschi, N.; Battaglia, P.; Togni, A. Tetrahedron Lett. 2010, 66, 5753
37. Kikugawa, Y.; Kawase, M. Chem. Lett. 1990, 581
38. Balthazar, T. M.; Miles, J. A.; Stults, B. R. J. Org. Chem. 1978, 43, 4538
39. Nemykin, V. N.; Maskaev, A. V.; Geraskina, M. R.; Yusubov, M. S.; Zhdankin, V. V. Inorg. Chem. 2011, 50, 11263
40. Jaffe, H.; Leffler, J. Eur. J. Org. Chem. 1975, 40, 797
41. Su, J. T.; Goddard, W. A. J. Am. Chem. Soc. 2005, 127, 14146
42. Guilbault, A. A.; Legault, C. Y. ACS Catal. 2012, 2, 219
43. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335
44. Ochiai, M.; Sueda, K.; Miyamoto, T.; Kiprof, P.; Zhdankin, V. V. Angew. Chem., Int. Ed. 2006, 45, 8203
45. Sajith, P. K.; Suresh, C. H. Inorg. Chem. 2012, 51, 967
46. Kiprof, P. ARKIVOC 2005, 19
47. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, U.K., 1990.
48. Gadre, S. R.; Shirsat, R. N. Electrostatics of Atoms and Molecules; Universities Press: Hyderabad, India, 2000.
49. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
50. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
51. 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.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01, Gaussian, Inc.: Wallingford, CT, 2009.
52. Sosa, C.; Andzelm, J.; Elkin, B. C.; Wimmer, E.; Dobbs, K. D.; Dixon, D. A. J. Phys. Chem. A 1992, 96, 6630
53. Yurieva, A. G.; Kh, P. O.; Filimonov, V. D. J. Struct. Chem. 2008, 49, 548
54. Politzer, P.; Truhlar, D. G. Chemical Applications of Atomic and Molecular Electrostatic Potentials; Plenum Press: New York, 1981.
55. Mathew, J.; Suresh, C. H. Inorg. Chem. 2010, 49, 4665
56. Sayyed, F. B.; Suresh, C. H. J. Phys. Chem. A 2012, 116, 5723
57. Suresh, C. H.; Alexander, P.; Vijayalakshmi, K. P.; Sajith, P. K.; Gadre, S. R. Phys. Chem. Chem. Phys. 2008, 10, 6492
58. König, F. B.; Schönbohm, J.; Bayles, D. J. Comput. Chem. 2001, 22, 545
59. Sajith, P. K.; Suresh, C. H. Dalton Trans. 2010, 39, 815
60. Sajith, P. K.; Suresh, C. H. J. Organomet. Chem. 2011, 696, 2086
61. Sajith, P. K.; Suresh, C. H. Inorg. Chem. 2011, 50, 8085
62. Anastasi, A. E.; Deeth, R. J. J. Chem. Theory Comput. 2009, 5, 2339
63. Deeth, R. J. J. Chem. Soc., Dalton Trans. 1993, 3711
64. Rigamonti, L.; Rusconi, M.; Manassero, C.; Manassero, M.; Pasini, A. Inorg. Chim. Acta 2010, 363, 3498
65. Rigamonti, L.; Manassero, C.; Rusconi, M.; Manassero, M.; Pasini, A. Dalton Trans. 2009, 1206
66. Rigamonti, L.; Forni, A.; Manassero, M.; Manassero, C.; Pasini, A. Inorg. Chem. 2010, 49, 123
67. Zefirov, N. S.; Zhdankin, V. V.; DanÌkov, Y. V.; Sorokin, V. D.; Semerikov, V. N.; Kozîmin, A. S.; Caple, R.; Berglund, B. A. Tetrahedron Lett. 1986, 27, 3971
68. Gately, D. A.; Luther, T. A.; Norton, J. R.; Miller, M. M.; Anderson, O. P. J. Org. Chem. 1992, 57, 6496
69. Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202
70. Ochiai, M.; Suefuji, T.; Miyamotoa, K.; Shirob, M. Chem. Commun. 2003, 1438
71. Ochiai, M.; Kitagawa, Y.; Takayama, N.; Takaoka, Y.; Shiro, M. J. Am. Chem. Soc. 1999, 121, 9233
72. Montanari, V.; DesMarteau, D. D.; Pennington, W. T. J. Mol. Struct. 2000, 337, 550
73. Edwards, A. J. J. Chem. Soc., Dalton Trans. 1978, 1723