A computational investigation of the role of the iridium dihydrogen pincer complex in the formation of the cyclic pentamer (NH 2BH 2) 5

Computational and Theoretical Chemistry

Volumn 992, Issue , 2012, Pages 18-29

  Ghatak, Kamalika ^a   Vanka, Kumar ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Ammonia borane; Hydrogen storage; Iridium pincer ligand catalyst; Mechanistic studies; Oligomerisation cycle

Indexed keywords

EID: 84863097832     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2012.04.020     Document Type: Article

References (63)

1. Eberle U., Felderhoff M., Schueth F. Chemical and physical solutions for hydrogen storage. Angew. Chem., Int. Ed. 2009, 48:6608-6630.
2. Zhang J., Fisher T.S., Ramachandran P.V., Gore J.P., Mudawar I. A review of heat transfer issues in hydrogen storage technologies. J. Heat Trans. 2005, 127:1391-1399.
3. Weitkamp J., Fritz M., Ernst S. Zeolites as media for hydrogen storage. Int. J. Hydrogen Energy 1995, 20:967-970.
4. Dinca M., Long J.R. Hydrogen storage in microporous metal-organic frameworks with exposed metal sites. Angew. Chem., Int. Ed. 2008, 47:6766-6779.
5. Rowsell J.L.C., Yaghi O.M. Strategies for hydrogen storage in metal-organic frameworks. Angew. Chem., Int. Ed. 2005, 44:4670-4679.
6. Sakintuna B., Lamari-Darkrim F., Hirscher M. Metal hydride materials for solid hydrogen storage: a review. Int. J. Hydrogen Energy 2007, 32:1121-1140.
7. Orimo S.-i., Nakamori Y., Eliseo J.R., Zuettel A., Jensen C.M. Complex hydrides for hydrogen storage. Chem. Rev. (Washington, DC, US) 2007, 107:4111-4132.
8. Staubitz A., Robertson A.P.M., Manners I. Ammonia-borane and related compounds as dihydrogen sources. Chem. Rev. (Washington, DC, US) 2010, 110:4079-4124.
9. Smythe N.C., Gordon J.C. Ammonia borane as a hydrogen carrier: dehydrogenation and regeneration. Eur. J. Inorg. Chem. 2010, 509-521.
10. Stephens F.H., Pons V., Baker R.T. Ammonia borane: the hydrogen source par excellence?. Dalton Trans. 2007, 2613-2626.
11. Marder T.B. Will we soon be fueling our automobiles with ammonia-borane?. Angew. Chem., Int. Ed. 2007, 46:8116-8118.
12. Mal S.S., Stephens F.H., Baker R.T. Transition metal catalysed dehydrogenation of amine-borane fuel blends. Chem. Commun. 2011, 47.
13. 2}+ fragment and their relevance to the transition-metal-mediated dehydrocoupling of amine-boranes. Inorg. Chem. 2010, 49:1111-1121.
14. Jaska C.A., Temple K., Lough A.J., Manners I. Rhodium-catalyzed formation of boron-nitrogen bonds: a mild route to cyclic aminoboranes and borazines. Chem. Commun. (Cambridge, UK) 2001, 962-963.
15. Jaska C.A., Temple K., Lough A.J., Manners I. Transition metal-catalyzed formation of boron-nitrogen bonds: catalytic dehydrocoupling of amine-borane adducts to form aminoboranes and borazines. J. Am. Chem. Soc. 2003, 125:9424-9434.
16. Clark T.J., Russell C.A., Manners I. Homogeneous, titanocene-catalyzed dehydrocoupling of amine-borane adducts. J. Am. Chem. Soc. 2006, 128:9582-9583.
17. 2 complexes. Chem. Commun. (Cambridge, UK) 2007, 3297-3299.
18. Forster T.D., Tuononen H.M., Parvez M., Roesler R. Characterization of b-B-agostic isomers in zirconocene amidoborane complexes. J. Am. Chem. Soc. 2009, 131:6689-6691.
19. Keaton R.J., Blacquiere J.M., Baker R.T. Base metal catalyzed dehydrogenation of ammonia borane for chemical hydrogen storage. J. Am. Chem. Soc. 2007, 129:1844-1845.
20. 3 (Cy=cyclohexyl). Inorg. Chem. (Washington, DC, US) 2009, 48:2429-2435.
21. Kaess M., Friedrich A., Drees M., Schneider S. Ruthenium complexes with cooperative PNP ligands: bifunctional catalysts for the dehydrogenation of ammonia-borane. Angew. Chem., Int. Ed. 2009, 48:905-907.
22. Blaquiere N., Diallo-Garcia S., Gorelsky S.I., Black D.A., Fagnou K. Ruthenium-catalyzed dehydrogenation of ammonia boranes. J. Am. Chem. Soc. 2008, 130:14034-14035.
23. Conley B.L., Williams T.J. Dehydrogenation of ammonia-borane by Shvo's catalyst. Chem. Commun. 2010, 46.
24. Conley B.L., Guess D., Williams T.J. A robust, air-stable, reusable ruthenium catalyst for dehydrogenation of ammonia borane. J. Am. Chem. Soc. 2011, 133:14212-14215.
25. Wright W.R.H., Berkeley E.R., Alden L.R., Baker R.T., Sneddon L.G. Transition metal catalysed ammonia-borane dehydrogenation in ionic liquids. Chem. Commun. 2011, 47.
26. 2]OTf. Eur. J. Inorg. Chem. 2009, 3055-3059.
27. Denney M.C., Pons V., Hebden T.J., Heinekey D.M., Goldberg K.I. Efficient catalysis of ammonia borane dehydrogenation. J. Am. Chem. Soc. 2006, 128:12048-12049.
28. Shrestha R.P., Diyabalanage H.V.K., Semelsberger T.A., Ott K.C., Burrell A.K. Catalytic dehydrogenation of ammonia borane in non-aqueous medium. Int. J. Hydrogen Energy 2009, 34:2616-2621.
29. Yang X., Hall M.B. The catalytic dehydrogenation of ammonia-borane involving an unexpected hydrogen transfer to ligated carbene and subsequent carbon-hydrogen activation. J. Am. Chem. Soc. 2008, 130:1798-1799.
30. 2 catalyzed dehydrogenation of ammonia-borane for chemical hydrogen storage. J. Organomet. Chem. 2009, 694:2831-2838.
31. Zimmerman P.M., Paul A., Musgrave C.B. Catalytic dehydrogenation of ammonia borane at ni monocarbene and dicarbene catalysts. Inorg. Chem. (Washington, DC, US) 2009, 48:5418-5433.
32. Zimmerman P.M., Paul A., Zhang Z., Musgrave C.B. The role of free N-heterocyclic carbene (NHC) in the catalytic dehydrogenation of ammonia borane in the nickel NHC system. Angew. Chem., Int. Ed. 2009, 48:2201-2205.
33. Paul A., Musgrave C.B. Catalyzed dehydrogenation of ammonia borane by iridium dihydrogen pincer complex differs from ethane dehydrogenation. Angew. Chem., Int. Ed. 2007, 46:8153-8156.
34. 2 with ammonia-borane. Inorg. Chem. (Washington, DC, US) 2009, 48:1069-1081.
35. Davis B.L., Dixon D.A., Garner E.B., Gordon J.C., Matus M.H., Scott B., Stephens F.H. Efficient regeneration of partially spent ammonia borane fuel. Angew. Chem., Int. Ed. 2009, 48:6812-6816. S6812/6811-S6812/6818.
36. Sutton A.D., Burrell A.K., Dixon D.A., Garner E.B., Gordon J.C., Nakagawa T., Ott K.C., Robinson J.P., Vasiliu M. Regeneration of ammonia borane spent fuel by direct reaction with hydrazine and liquid ammonia. Science 2011, 331:1426-1429.
37. 2 release in metal-catalysed ammonia borane dehydrogenation. Chem. Commun. (Cambridge, UK) 2008, 6597-6599.
38. 2)n. J. Am. Chem. Soc. 1966, 88:4396-4401.
39. Ahlrichs R., Baer M., Haeser M., Horn H., Koelmel C. Electronic structure calculations on workstation computers: the program system TURBOMOLE. Chem. Phys. Lett. 1989, 162:165-169.
40. Becke A.D. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A Gen. Phys. 1988, 38:3098-3100.
41. Perdew J.P. Density-functional approximation for the correlation-energy of the inhomogeneous electron-gas. Phys. Rev. B 1986, 33:8822-8824.
42. Weigend F. A fully direct RI-HF algorithm: Implementation, optimised auxiliary basis sets, demonstration of accuracy and efficiency. Phys. Chem. Chem. Phys. 2002, 4:4285-4291.
43. Weigend F., Ahlrichs R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys. Chem. Chem. Phys. 2005, 7:3297-3305.
44. Schaefer A., Horn H., Ahlrichs R. Fully optimized contracted Gaussian basis sets for atoms lithium to krypton. J. Chem. Phys. 1992, 97:2571-2577.
45. Schaefer A., Huber C., Ahlrichs R. Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr. J. Chem. Phys. 1994, 100:5829-5835.
46. Perdew J.P., Burke K., Ernzerhof M. Generalized gradient approximation made simple. Phys. Rev. Lett. 1996, 77:3865-3868.
47. Eichkorn K., Treutler O., Oehm H., Haeser M., Ahlrichs R. Auxiliary basis sets to approximate Coulomb potentials. Chem. Phys. Lett. 1995, 240:283-290.
48. Sierka M., Hogekamp A., Ahlrichs R. Fast evaluation of the Coulomb potential for electron densities using multipole accelerated resolution of identity approximation. J. Chem. Phys. 2003, 118:9136-9148.
49. Hattig C., Weigend F. CC2 excitation energy calculations on large molecules using the resolution of the identity approximation. J. Chem. Phys. 2000, 113:5154-5161.
50. Klamt A. Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena. J. Phys. Chem. 1995, 99:2224-2235.
51. Mammen M., Shakhnovich E.I., Whitesides G.M. Using a convenient, quantitative model for torsional entropy to establish qualitative trends for molecular processes that restrict conformational freedom. J. Org. Chem. 1998, 63:3168-3175.
52. 2. Angew. Chem., Int. Ed. 2010, 49:918-920. S918/911-S918/914.
53. Dallanegra R., Chaplin A.B., Tsim J., Weller A.S. Amino-borane oligomers bound to a Rh(I) metal fragment. Chem. Commun. (Cambridge, UK) 2010, 46:3092-3094.
54. Dallanegra R., Chaplin A.B., Weller A.S. Bis(s-amine-borane) complexes: an unusual binding mode at a transition-metal center. Angew. Chem., Int. Ed. 2009, 48:6875-6878. S6875/6871-S6875/6815.
55. 3: intermediates and catalysis. Chem. - A Euro. J. 2010, 16:8508-8515.
56. Spielmann J., Jansen G., Bandmann H., Harder S. Calcium amidoborane hydrogen storage materials: crystal structures of decomposition products. Angew. Chem. 2008, 120:6386-6391.
57. Li Z., Zhu G., Lu G., Qiu S., Yao X. Ammonia borane confined by a metal-organic framework for chemical hydrogen storage: enhancing kinetics and eliminating ammonia. J. Am. Chem. Soc. 2010, 132:1490-1491.
58. Shaw W.J., Linehan J.C., Szymczak N.K., Heldebrant D.J., Yonker C., Camaioni D.M., Baker R.T., Autrey T. In situ multinuclear NMR spectroscopic studies of the thermal decomposition of ammonia borane in solution. Angew. Chem., Int. Ed. 2008, 47:7493-7496.
59. 3. J. Phys. Chem. A 2007, 111:679-690.
60. Nutt W.R., McKee M.L. Theoretical study of reaction pathways to borazine. Inorg. Chem. (Washington, DC, US) 2007, 46:7633-7645.
61. Staubitz A., Sloan M.E., Robertson A.P.M., Friedrich A., Schneider S., Gates P.J., Gunne J.r.S.a.d., Manners I. Catalytic dehydrocoupling/dehydrogenation of N-methylamine-borane and ammonia-borane: synthesis and characterization of high molecular weight polyaminoboranes. J. Am. Chem. Soc. 2010, 132:13332-13345.
62. Dietrich B.L., Goldberg K.I., Heinekey D.M., Autrey T., Linehan J.C. Iridium-catalyzed dehydrogenation of substituted amine boranes: kinetics, thermodynamics, and implications for hydrogen storage. Inorg. Chem. (Washington, DC, US) 2008, 47:8583-8585.
63. Reed A.E., Weinstock R.B., Weinhold F. Natural-population analysis. J. Chem. Phys. 1985, 83:735-746.