Rhodium complexes of 1,3-diaryltriazenes: Usual coordination, N-H bond activation and, N-N and C-N bond cleavage

Journal of Organometallic Chemistry

Volumn 693, Issue 26, 2008, Pages 3923-3931

  GuhaRoy, Chhandasi ^a   Butcher, Ray J ^b   Bhattacharya, Samaresh ^a  

^a JADAVPUR UNIVERSITY   (India)

^b HOWARD UNIVERSITY   (United States)

Author keywords

1 Aryl complexes; 1,3 Diaryltriazenes; N H bond activation; N N and C N bond cleavage; Rhodium

Indexed keywords

CHEMICAL OXYGEN DEMAND; COORDINATION REACTIONS; CRYSTALLOGRAPHY; CYCLIC VOLTAMMETRY; ETHANOL; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REACTION KINETICS; RHODIUM; TOLUENE; VANADIUM COMPOUNDS; X RAY CRYSTALLOGRAPHY;

1,3-DIARYLTRIAZENES; AMBIENT CONDITIONS; BOND CLEAVAGES; DOUBLE BONDS; H BONDS; IRREVERSIBLE REDUCTIONS; N-H BOND ACTIVATION; N-N AND C-N BOND CLEAVAGE; NMR SIGNALS; PARA POSITIONS; PROTONATED; RHODIUM COMPLEXES; TRIAZENES; VISIBLE REGIONS; X-RAY CRYSTALLOGRAPHIES;

RHODIUM COMPOUNDS;

EID: 56349150397     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.10.006     Document Type: Article

References (113)

1. Jardine F.H. Prog. Inorg. Chem. 28 (1981) 63
2. Baksi S., Acharyya R., Basuli F., Peng S.M., Lee G.H., Nethaji M., and Bhattacharya S. Organometallics 26 (2007) 6596
3. Baksi S., Acharyya R., Dutta S., Blake A.J., Drew M.G.B., and Bhattacharya S. J. Organomet. Chem. 692 (2007) 1025
4. Basu S., Dutta S., Drew M.G.B., and Bhattacharya S. J. Organomet. Chem. 691 (2006) 3581
5. Acharyya R., Dutta S., Basuli F., Peng S.M., Lee G.H., Falvello L.R., and Bhattacharya S. Inorg. Chem. 45 (2006) 1252
6. Basu S., Pal I., Butcher R.J., Rosair G., and Bhattacharya S. J. Chem. Sci. 117 (2005) 167
7. Basu S., Peng S.M., Lee G.H., and Bhattacharya S. Polyhedron 24 (2005) 157
8. Acharyya R., Basuli F., Rosair G., and Bhattacharya S. New J. Chem. 28 (2004) 115
9. Pal I., Dutta S., Basuli F., Goverdhan S., Peng S.M., Lee G.H., and Bhattacharya S. Inorg. Chem. 42 (2003) 4338
10. Dutta S., Basuli F., Peng S.M., Lee G.H., and Bhattacharya S. New J. Chem. 26 (2002) 1607
11. Das A., Basuli F., Peng S.M., and Bhattacharya S. Inorg. Chem. 41 (2002) 440
12. Dutta S., Peng S.M., and Bhattacharya S. J. Chem. Soc., Dalton Trans. (2000) 4623
13. Dutta S., Peng S.M., and Bhattacharya S. Inorg. Chem. 39 (2000) 2231
14. Nimitsiriwat N., Gibson V.C., Marshall E.L., Takolpuckdee P., K Tomov A., White A.J.P., Williams D.J., Elsegood M.R.J., and Dale S.H. Inorg. Chem. 46 (2007) 9988
15. Albertin G., Antoniutti S., Bedin M., Castro J., and Garcia-Fontan S. Inorg. Chem. 45 (2006) 3816
16. Clark T., Cochrane J., Colson S.F., Malik K.Z., Robinson S.T., and Steed J.W. Polyhedron 20 (2001) 1875
17. Pfeiffer D., Guzei I.A., Liable-Sands L.M., Heeg M.J., Rheingold A.L., and Winter C.H. J. Organomet. Chem. 588 (1999) 167
18. Westhusin S., Gantzel P., and Walsh P.J. Inorg. Chem. 37 (1998) 5956
19. Menon M., Pramanik A., Chattopadhyay S., Bag N., and Chakravorty A. Inorg. Chem. 34 (1995) 1361
20. Leman J.T., Braddock-Wilking J., Coolong A.J., and Barron A.R. Inorg. Chem. 32 (1993) 4324
21. Colson S.F., and Robinson S.D. Polyhedron 9 (1990) 1737
22. Carriedo C., Connelly N.G., Hettrich R., Orpen A.G., and White A.M.J. J. Chem. Soc., Dalton Trans. (1989) 745
23. Hillhouse G.L., and Haymore B.L. Inorg. Chem. 26 (1987) 1876
24. Queiros M.A.M., Simao J.E.J., and Dias A.R. J. Organomet. Chem. 329 (1987) 85
25. Creswell C.J., Queiros M.A.M., and Robinson S.D. Inorg. Chim. Acta 60 (1982) 157
26. Immirzi A., Porzio W., Bombieri G., and Toniolo L. J. Chem. Soc., Dalton Trans. (1980) 1098
27. Brown L.D., and Ibers J.A. J. Am. Chem. Soc. 98 (1976) 1597
28. Nuricumbo-Escobar J.J., Campos-Alvarado C., Rios-Moreno G., Morales-Morales D., Walsh P.J., and Parra-Hake M. Inorg. Chem. 46 (2007) 6182
29. Adams C.J., Baber R.A., Connelly N.O., Hardeng P., Hayward O.D., Kandiah M., and Orpen A.G. J. Chem. Soc., Dalton Trans. 13 (2007) 1325
30. Tejel C., Ciriano M.A., Rios-Moreno G., Dobrinovitch I.T., Lahoz F.J., Oro L.A., and Parra-Hake M. Inorg. Chem. 43 (2004) 4719
31. Connelly N.G., Hayward O.D., Klangsinsirikul P., and Orpen A.G. J. Chem. Soc., Dalton Trans. (2002) 305
32. Ruiz J., Lopez G.F.J., Rodriguez V., Perez J., Ramirez de Arellano M.C., and Lopez G. J. Chem. Soc., Dalton Trans. (2001) 2683
33. Gantzel P., and Walsh P.J. Inorg. Chem. 37 (1998) 3450
34. Ang H.G., Koh L.L., and Yang G.Y. J. Chem. Soc., Dalton Trans. 8 (1996) 1573
35. Connelly N.G., Einig T., Garcia G., Herbosa G., Hopkins P.M., Mealli C., Orpen A.G., Rosair G.M., and Viguri F. J. Chem. Soc., Dalton Trans. (1994) 2025
36. Hursthouse M.B., Mazid M.A., Clark T., and Robinson D. Polyhedron 12 (1993) 563
37. Connelly N.G., and Garcia G. J. Chem. Soc., Dalton Trans. (1987) 2737
38. Smith M.B.K., Taneyhill L.A., Michejda C.J., and Smith Jr. R.H. Chem. Res. Toxicol. 9 (1996) 341
39. McConnaughie A.M., and Jenkins T.C. J. Med. Chem. 38 (1995) 3488
40. Smith Jr. R.H., Scudiero D.A., and Michejda C.J. J. Med. Chem. 33 (1990) 2579
41. 3).
42. 2 complex is yellowish orange.
43. Cavaglioni A., and Cini R. J. Chem. Soc., Dalton Trans. (1997) 1149
44. Cini R., Giorgi G., and Pasquini L. Inorg. Chim. Acta 196 (1992) 7
45. Hartwig J.F., Bergman R.G., and Andersen R.A. J. Am. Chem. Soc. 113 (1991) 3404
46. Calhorda M.J. Chem. Commun. (2000) 801
47. Janiak C., Temizdemir S., and Dechert S. Inorg. Chem. Commun. 3 (2000) 271
48. Janiak C., Temizdemir S., Dechert S., Deck W., Girgsdies F., Heinze J., Kolm M.J., Scarmann T.G., and Zipffel O.M. Eur. J. Inorg. Chem. (2000) 1229
49. Desiraju G.R., and Steiner T. The Weak hydrogen Bond (IUCr Monograph on Crystallography 9) (1999), Oxford Science Pub.
50. Hannon M.J., Painting C.L., and Alcock N.W. Chem. Commun. (1999) 2023
51. Mcnelis B.J., Nathan L.C., and Clark C.J. J. Chem. Soc., Dalton Trans. (1999) 1831
52. Biradha K., Seward C., and Zaworotko M.J. Angew. Chem., Int. Ed. 38 (1999) 492
53. Burley S.K., and Petsko G.A. Adv. Protein Chem. 39 (1998) 125
54. Nishio M., Hirota M., and Umezawa Y. The CH⋯π Interactions (Evidence, Nature and Consequences) (1998), Wiley-VCH, New York
55. Umezawa Y., Tsuboyama S., Honda K., Uzawa J., and Nishio M. Bull. Chem. Soc. Jpn. 71 (1998) 1207
56. Madhavi N.N.L., Katz A.K., Carrell H.L., Nangia A., and Desiraju G.R. Chem. Commun. (1997) 1953
57. Weiss H.C., Blaser D., Boese R., Doughan B.M., and Haley M.M. Chem. Commun. (1997) 1703
58. Kilah N.L., Patrie S., Stranger R., Wielandt J.W., Willis A.C., and Wild S.B. Organometallics 26 (2007) 6106
59. Roy A.H., Lenges C.P., and Brookhart M. J. Am. Chem. Soc. 129 (2007) 2082
60. Zhao P., Incarvito C.D., and Hartwig J.F. J. Am. Chem. Soc. 129 (2007) 1876
61. Diez V., Espino G., Jalon F.A., Manzano B.R., and Perez-Manrique M. J. Organomet. Chem. 692 (2007) 1482
62. Mochida K., Fukushima T., Suzuki M., Hatanaka W., Takayama M., Usui Y., Nanjo M., Akasaka K., Kudo T., and Komiya S. J. Organomet. Chem. 692 (2007) 395
63. Hoseini S.J., Mohamadikish M., Kamali K., Heinemann F.W., and Rashidi M. J. Chem. Soc., Dalton Trans. (2007) 1697
64. Nilson P., Puxty G., and Wendt O.F. Organometallics 25 (2006) 1285
65. Vicente J., Arcas A., Galvez-Lopez M.-D., and Jones P.G. Organometallics 25 (2006) 4247
66. Adamo C., Amatore C., Ciofini I., Jutland A., and Lakmini H. J. Am. Chem. Soc. 128 (2006) 6829
67. Zhao P., Incarvito C.D., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 3124
68. Yahav A., Goldberg I., and Vigalok A. Inorg. Chem. 44 (2005) 1547
69. Wang X., Lane B.S., and Sames D. J. Am. Chem. Soc. 127 (2005) 4996
70. Zhao P., and Hartwig J.F. J. Am. Chem. Soc. 127 (2005) 11618
71. Casares J.A., Espinet P., Martin-Alvarez J.M., Martinez-Ilarduya J.M., and Salas G. Eu. J. Inorg. Chem. (2005) 3825
72. Taw F.L., Mueller A.H., Bergman R.G., and Brookhart M. J. Am. Chem. Soc. 125 (2003) 9808
73. Taw F.L., White P.S., Bergman R.G., and Brookhart M. J. Am. Chem. Soc. 124 (2002) 4192
74. Cotton F.A., Daniels L.M., Murillo CA., and Wang X. Inorg. Chem. 36 (1997) 896
75. Cotton F.A., Matonic J.H., Murillo C.A., and Wang X. Bull. Soc. Chim. Fr. 133 (1996) 711
76. Proulx G., and Bergman R.G. J. Am. Chem. Soc. 116 (1994) 7953
77. Cummins C.C., Shrock R.R., and Davis W.M. Inorg. Chem. 33 (1994) 1448
78. Agadorn J.R., and Arnold J. Organometallics 13 (1994) 4670
79. Atagi L.M., Over D.E., McAlister D.R., and Mayer J.M. J. Am. Chem. Soc. 113 (1991) 870
80. Ueno S., Chatani N., and Kakiuchi F. J. Am. Chem. Soc. 129 (2007) 6098
81. Saeki T., Son E.-C., and Tamao K. Org. Lett. 7 (2004) 617
82. Ozerov O.V., Guo C., Papkov V.A., and Foxman B.M. J. Am. Chem. Soc. 126 (2004) 4792
83. Hu C., Chin R.M., Nguyen T.D., Nguyen K.T., and Wagenknecht P.S. Inorg. Chem. 42 (2003) 7602
84. Cameron T.M., Abboud K.A., and Boncella M.J. Chem. Commun. (2001) 1224
85. Werner H., Horlin G., and Jones W.D. J. Organomet. Chem. 562 (1998) 45
86. Kleckley T.S., Bennett J.L., Wolczanski P.T., and Lobkovsky E.B. J. Am. Chem. Soc. 119 (1997) 247
87. Rodriguez M.-C., Lambert F., and Morgenstern-Badarau I. Inorg. Chem. 36 (1997) 3525
88. Cotton F.A., Daniela L.M., Murillo C.A., and Wang X. Inorg. Chem. 36 (1997) 896
89. Hagadorn J.H., and Arnold J. Organometallics 13 (1994) 4670
90. CelenligilCetin R., Watson L.A., Guo C., Foxman B.M., and Ozerov O.V. Organometallics 24 (2005) 186
91. Li T., Churlaud R., Lough A.J., Abdur-Rashid K., and Morris R.H. Organometallics 23 (2004) 6239
92. Yi C.S., Yun S.Y., and Guzei I.A. Organometallics 23 (2004) 5392
93. The evolved gas could not be detected.
94. Laing K.R., Robinson S.D., and Uttley M.F. J. Chem. Soc., Dalton Trans. (1974) 1205
95. 3); 6.99 (d, 12H, J = 8.6); 7.16 (d, 12H, J = 8.1)].
96. Mealli C., and Proserpio D.M. J. Chem. Educ. 67 (1990) 399
97. In the 1-R and 2-R complexes the phenyl rings of the triphenylphosphines have been replaced by hydrogens.
98. 2 fragments.
99. 2 complexes.
100. Cook M.J., Lewis A.P., Thomson G.S.J., Glasper J.L., and Robbins D.J. J. Chem. Soc., Perkin Trans. (1984) 293
101. Crosby G.A., and Elfring Jr. W.H. J. Phys. Chem. 80 (1976) 2206
102. A little dichloromethane was necessary to take the complex into solution. Addition of large excess of acetonitrile was necessary to record the redox responses in proper shape.
103. 2 complexes only one oxidation have been observed, probably because the other oxidation occurs beyond the voltage window.
104. 1-bound aryl fragment was also assumed to have the same σ-value as the other four substituents on the two coordinated triazene ligands.
105. Hammett L.P. Physical Organic Chemistry. second ed. (1970), McGraw Hill, New York
106. Mukherjee R.N., Rajan O.A., and Chakravorty A. Inorg. Chem. 21 (1982) 785
107. Osborn J.A., and Wilkinson G. Inorg. Synth. 10 (1967) 67
108. Hartman W.W., and Dickey J.B. Org. Synth. 2 (1943) 163
109. Sawyer D.T., and Roberts Jr. J.L. Experimental Electrochemistry for Chemists (1974), Wiley, New York pp. 167-215
110. Walter M., and Ramaley L. Anal. Chem. 45 (1973) 165
111. Chemical shifts are given in ppm and multiplicity of the signals along with the associated coupling constants (J in Hz) are given in parentheses. Overlapping signals are marked with an asterisk.
112. The 2-R complexes are also obtained in similar yield in the absence of any base.
113. Sheldrick G.M. shelxs-97 and shelxl-97, Fortran Programs for Crystal Structure Solution and Refinement (1997), University of Gottingen, Gottingen, Germany