Differences between Amine-and Phosphine-Boranes: Synthesis, Photoelectron Spectroscopy, and Quantum Chemical Study of the Cyclopropylic Derivatives

Inorganic Chemistry

Volumn 49, Issue 11, 2010, Pages 4854-4864

  Németh, Balázs ^a,b   Khater, Brahim ^a   Guillemin, Jean Claude ^a   Veszprémi, Tamás ^b  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BORANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; METHODOLOGY; QUANTUM THEORY; SYNTHESIS; X RAY PHOTOELECTRON SPECTROSCOPY;

AMINES; BORANES; COMPUTER SIMULATION; CYCLOPROPANES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PHOSPHINES; PHOTOELECTRON SPECTROSCOPY; QUANTUM THEORY;

EID: 77953055645     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic902180p     Document Type: Article

References (78)

1. Stephens, F. H., Baker, R. T., Matus, M. H., Grant, D. J., and Dixon, D. A. Angew. Chem., Int. Ed. 2007, 46, 746-749
2. Bluhm, M. E., Bradley, M. G., Butterick, R., III, Kusari, U., and Sneddon, L. G. J. Am. Chem. Soc. 2006, 128, 7748-7749
3. Dixon, D. A. and Gutowski, M. J. Phys. Chem. A 2005, 109, 5129-5135
4. Nguyen, M. T., Nguyen, V. S., Mathus, M. H., Gopakumar, G., and Dixon, D. A. J. Phys. Chem. A 2007, 111, 679-690
5. Gopakumar, G., Nguyen, V. S., and Nguyen, M. T. THEOCHEM 2007, 811, 77-89
6. Grant, D. J. and Dixon, D. A. J. Phys. Chem. A 2005, 109, 10138-10147
7. Denney, M. C., Pons, V., Hebden, T. J., Heinekey, D. M., and Goldberg, K. I. J. Am. Chem. Soc. 2006, 128, 12048-12049
8. Dietrich, B. L., Goldberg, K. I., Heinekey, D. M., Autrey, T., and Linehan, J. C. Inorg. Chem. 2008, 47, 8583-8585
9. Blaquiere, N., Diallo-Garcia, S., Gorelsky, S. I., Black, D. A., and Fagnou, K. J. Am. Chem. Soc. 2008, 130, 14034-14035
10. Grant, J., Matus, M. H., Anderson, K. D., Camaioni, D. M., Neufeldt, S. R., Lane, C. F., and Dixon, D. A. J. Phys. Chem. A 2009, 113, 6121-6132
11. Sun, C.-H., Yao, X.-D., Du, A.-J., Li, L., Smith, S., and Lu, G.-Q. Phys. Chem. Chem. Phys. 2008, 10, 6104-6106
12. Aldridge, S., Downs, A. J., Tang, C. Y., Parsons, S., Clarke, M. C., Johnstone, R. D. L., Robertson, H. E., Rankin, D. W. H., and Wann, D. A. J. Am. Chem. Soc. 2009, 131, 2231-2243
13. Noble-Eddy, R., Masters (née Hinchley), S. L., Rankin, D. W. H., Wann, D. A., Khater, B., and Guillemin, J.-C. Dalton Trans. 2008, 5041-5047
14. Németh, B., Khater, B., Veszpémi, T., and Guillemin, J.-C. Dalton Trans. 2009, 3526-3335
15. de Meijere, A. Methoden der Organischen Chemie (Houben-Weyl) Vol. E17: Carbocyclic Three and Four-Membered Ring Compounds; Thieme: Stuttgart, Germany, 1996.
16. de Meijere, A. Angew. Chem., Int. Ed. 1979, 18, 809-826
17. Nijveldt, D. and Vos, A. Acta Crystallogr., Sect. B 1988, 44, 296-307
18. Hoffmann, R. Tetrahedron Lett. 1970, 11, 2907-2909
19. Günther, H. Tetrahedron Lett. 1970, 11, 5173-5176
20. Haumann, T., Boese, R., Kozhushkov, S. I., Rauch, K., and de Meijere, A. Liebigs Ann. Recueil 1997, 2047-2053
21. de Meijere, A., Jaeckel, F., Simon, A., Bormann, H., Köhler, J., Johnels, D., and Scott, L. T. J. Am. Chem. Soc. 1991, 113, 3935-3941
22. Olah, G. A., Prakash, R., Rasul, G., and Prakash, G. K. S. J. Am. Chem. Soc. 1999, 121, 9994-9998
23. Bruckmann, P. and Klessinger, M. Chem. Ber. 1974, 107, 1108-1125
24. Askani, R., Gleiter, R., Heilbronner, E., Hornung, V., and Musso, H. Tetrahedron Lett. 1971, 12, 4461-4466
25. Harada, Y., Seki, K., Suzuki, A., and Inokuchi, H. Chem. Lett. 1973, 2, 893-896
26. Rademacher, P. Chem. Rev. 2003, 103, 933-976
27. Kimura, S., Ito, S., Yoshifuji, M., and Veszprémi, T. J. Org. Chem. 2003, 68, 6820-6823
28. Hendricksen, D. K. and Harmony, M. D. J. Chem. Phys. 1969, 51, 700-705
29. Kimura, K., Katsumata, S., Achiba, Y., Yamazaki, T., and Iwata, S. Handbook of HeI Photoelectron Spectra of Fundamental Organic Molecules; Japan Scientific Societies Press: Tokyo; Halsted Press: New York, 1981.
30. Yamakado, H., Ogawa, T., and Ohno, K. J. Phys. Chem. A 1997, 101, 3887-3894
31. Dinsmore, L. A., Britt, C. O., and Boggs, J. E. J. Chem. Phys. 1971, 54, 915-918
32. Pelissier, M., Leibovici, C., and Labarre, J.-F. Tetrahedron 1972, 28, 4825-4833
33. Clark, T., Spitznagel, G. W., Klose, R., and Schleyer, P. v. R. J. Am. Chem. Soc. 1984, 106, 4412-4419
34. Cremer, D. and Kraka, E. J. Am. Chem. Soc. 1985, 107, 3811-3819
35. Wiberg, K. B. and Laidig, K. E. J. Org. Chem. 1992, 57, 5092-5101
36. Rademacher, P., Kowski, K., de Meijere, A., and Chaplinski, V. J. Mol. Struct. 1994, 323, 135-138
37. Plant, C., Spencer, K., and Macdonald, J. N. J. Chem. Soc., Faraday Trans. 2 1987, 83 (8) 1411-1425
38. Khater, B., Guillemin, J.-C., Bajor, G., and Veszprémi, T. Inorg. Chem. 2008, 47, 1502-1511
39. Wystrach, V. P., Kaiser, D. W., and Schaefer, F. C. J. Am. Chem. Soc. 1955, 77, 5915-5918
40. Wagner, R. I., LeVern, D. F., Goldwhite, H., and Rowsell, D. G. J. Am. Chem. Soc. 1967, 89, 1102-1104
41. Cole, G. C., Mllendal, H., and Guillemin, J.-C. J. Phys. Chem. A 2005, 109, 7134-7139
42. Burg, A. B. and Good, C. D. J. Inorg. Nucl. Chem. 1956, 2, 237-245
43. Johnson, K. M., Kirwan, J. N., and Roberts, B. P. J. Chem. Soc. Perkin Trans 2 1990, 1125-1132
44. Hurtado, M., Yánez, M., Herrero, R., Guerrero, A., Dávalos, J. Z., Abboud, J.-L. M., Khater, B., and Guillemin, J.-C. Chem. Eur. J. 2009, 15, 4622-4629
45. Pasumansky, L., Haddenham, D., Clary, J. W., Fisher, G. B., Goralski, C. T., and Singaram, B. J. Org. Chem. 2008, 73, 1898-1905
46. Reed, A. E., Weinstock, R. B., and Weinhold, F. J. Chem. Phys. 1985, 83, 735-746
47. Wiberg, K. Tetrahedron 1968, 24, 1083-1096
48. Simon, S., Duran, M., and Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024-11031
49. Boys, S. F. and Bernardi, F. Mol. Phys. 1970, 19, 553-566
50. Marstokk, K.-M. and Mllendal, H. Acta Chem. Scand. A 1984, 38, 387-398
51. Cole, G. C., Mllendal, H., and Guillemin, J.-C. J. Phys. Chem. A 2005, 109, 7134-7139
52. Haaland, A. Angew. Chem., Int. Ed. 1989, 28, 992-1007
53. Staubitz, A., Besora, M., Harvey, N. J., and Manners, I. Inorg. Chem. 2008, 47, 5910-5918
54. Pokon, E. K., Liptak, M. D., Feldgus, S., and Shields, G. C. J. Phys. Chem. A 2001, 105, 10483-10487
55. Matus, M. H., Anderson, K., Camaioni, D. M., Autrey, S. T., and Dixon, D. A. J. Phys. Chem A. 2007, 111, 4411-4421
56. Merrick, J. P., Moran, D., and Radom, L. J. Phys. Chem. A 2007, 111, 11683-11700
57. Baitalow, F., Baumann, J., Wolf, G., Jaenicke-Rossler, K., and Leitner, G. Thermochim. Acta 2002, 391, 159-168
58. Burg, A. B. and Randolph, C. L., Jr. J. Am. Chem. Soc. 1949, 71, 3451-3455
59. Jaska, C. A., Temple, K., Lough, A., and Manners, I J. Am. Chem. Soc. 2003, 125, 9424-9434
60. Chen, Y., Fulton, J. L., Linehan, J. C., and Autrey, T. J. Am. Chem. Soc. 2005, 127, 3254-3255
61. Luo, Y. and Ohno, K. Organometallics 2007, 26, 3597-3600
62. Friedlich, A., Drees, M., and Schneider, S. Chem. Eur. J. 2009, 15, 10339-10342
63. Douglas, T. M., Chaplin, A. B., Weller, A. S., Áyand, X., and Hall, M. B. J. Am. Chem. Soc. 2009, 131, 15440-15456
64. Chapin, A. B. and Weller, A. S. Inorg. Chem. 2010, 49, 1111-1121
65. Basch, H., Robin, M. B., and Kuebler, N. A. J. Chem. Phys. 1969, 51, 52-66
66. Aue, D. H., Webb, H. M., Davidson, W. R., Vidal, M., Bowers, M. T., Goldwhite, H., Vertal, L. E., Douglas, J. E., Kollman, P. A., and Kenyon, G. L. J. Am. Chem. Soc. 1980, 102, 5151-5157
67. Ortiz, J. V., Zakrzewski, V. G., and Dolgounircheva, O. In Conceptual Perspectives in Quantum Chemistry; Calais, J.-L. and Kryachko, E., Eds.; Kluwer Academic: Norwell, MA, 1997; pp 465-517.
68. Cowley, A. H., Kemp, R. A., Lattman, M., and McKee, M. L. Inorg. Chem. 1982, 21, 85-88
69. Katrib, A. and Rabalais, J. W. J. Phys. Chem. 1973, 77, 2358-2363
70. Le Serre, S., Guillemin, J.-C., Kárpáti, T., Soos, L., Nyulászi, L., and Veszprémi, T. J. Org. Chem. 1998, 63, 59-68
71. Mllendal, H., Konovalov, A., and Guillemin, J.-C. J. Phys. Chem. A, 2009, 113, 12904-12910. DOI: 10.1021/jp907.
72. Zafrani, Y., Chen, R., Ashkenazi, N., and Segall, Y. Synth. Commun. 2008, 38, 848-857
73. Kövér, L., Kövér, Á., Cserny, I., Veszprémi, T., and Zsombok, Gy. Surf. Interface Anal. 1986, 9, 69
74. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
75. Lee, C., Yang, W., and Parr, R. G. Phys. Rev. B 1988, 37, 785-789
76. Singh, R. K. and Mishra, M. K. J. Phys. Chem. A 2009, 113, 14150-14155
77. 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., Bakken, V., 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, revision C.02; Gaussian, Inc. L Wallingford, CT, 2004.
78. Only theoretical studies have been performed on this compound: Solling, T. I., Wild, S. B., and Radom, L. J. Organomet. Chem. 1999, 580, 320-327