This article was published as part of the 2009 Renewable Energy issue Reviewing the latest developments in renewable energy research Guest Editors Professor Daniel Nocera and Professor Dirk Guldi Please take a look at the issue 1 table of contents to access the other reviews. Downloaded on 10 April 2012 Published on 26 November 2008 on http://pubs.rsc.org | doi:10.1039/B800312M View Online / Journal Homepage / Table of Contents for this issue
This document is posted to help you gain knowledge. Please leave a comment to let me know what you think about it! Share it to your friends and learn new things together.
Transcript
This article was published as part of the
2009 Renewable Energy issueReviewing the latest developments in renewable
energy research Guest Editors Professor Daniel Nocera and Professor Dirk Guldi
Please take a look at the issue 1 table of contents to access the other reviews.
Dow
nloa
ded
on 1
0 A
pril
2012
Publ
ishe
d on
26
Nov
embe
r 20
08 o
n ht
tp://
pubs
.rsc
.org
| do
i:10.
1039
/B80
0312
MView Online / Journal Homepage / Table of Contents for this issue
B–N compounds for chemical hydrogen storagewzCharles W. Hamilton,
aR. Tom Baker,*
bAnne Staubitz
cand Ian Manners*
c
Received 22nd September 2008
First published as an Advance Article on the web 26th November 2008
DOI: 10.1039/b800312m
Hydrogen storage for transportation applications requires high volumetric and gravimetric
storage capacity. B–N compounds are well suited as storage materials due to their light weight
and propensity for bearing multiple protic (N–H) and hydridic (B–H) hydrogens. This critical
review briefly covers the various methods of hydrogen storage, and then concentrates on chemical
hydrogen storage using B–N compounds. The simplest B–N compound, ammonia borane
(H3NBH3), which has a potential 19.6 wt% hydrogen storage capacity, will be emphasised
(127 references).
Introduction
An abundant, inexpensive energy supply is an essential com-
ponent to boost developing economies as well as maintain
status quo for established economies. Current energy con-
sumption is based on combustion of carbon-based fuels to
water and carbon dioxide (as well as environmentally harmful
carbon particulates and sulfur and nitrogen oxides). For many
years, climate modelling has shown that increased carbon
dioxide concentration in the atmosphere will lead to detri-
mental environmental effects (recently reiterated in the fourth
IPCC report).1 Thus it is vitally important to institute a shift
away from carbon-based fuels and toward environmentally-
friendly replacements.
The transportation sector represented 31(28)% of the
EU(US) energy use in 2005(2006) and accounted for
21(34)% of CO2 emissions.2,3 For stationary energy applica-
tions, CO2 can be potentially sequestered.4 For portable
energy, however, this is impractical and an alternative energy
carrier must be used.
Hydrogen has the potential to be a clean, source-independent,
energy carrier.5 It has a high energy content per mass
compared to petroleum (120 MJ kg�1 for hydrogen versus
44 MJ kg�1 for petroleum). Also, hydrogen can be readily used
to run a fuel cell, which greatly increases efficiency over internal
combustion engines (B32% efficiency for diesel-electric; 90%
potential efficiency for fuel cell with heat capture, 85% for
electric motor, 77% overall efficiency) while eliminating for-
mation of carbon particulates and sulfur and nitrogen oxides.6
a Los Alamos National Laboratory, Inorganic, Isotope, and ActinideChemistry, MS J582, Los Alamos, NM 87545, USA.E-mail: [email protected]; Fax: +1 505-667-3502;Tel: +1 505-665-4636
bDepartment of Chemistry, University of Ottawa, 10 Marie Curie,Ottawa, Ontario, Canada K1N 6N5. E-mail: [email protected];Tel: +1 613-562-5800 ext. 5698; +1 613-562-5800 ext. 5613
cUniversity of Bristol, School of Chemistry, Cantock’s Close, Bristol,UK BS8 1TS. E-mail: [email protected];Fax: +44 (0)117 929 0509w Part of the renewable energy theme issue.z Dedicated to Prof. M. Frederick Hawthorne on the occasion of his80th birthday.
Charles W. Hamilton
Charles Wayne Hamilton wasborn in Houston, Texas, USA.He received his BS in Chem-istry from Texas A&M Uni-versity in May of 2001.During his undergrad, he stu-died nuclear chemistry at theCyclotron Institute under thedirection of Prof. Joseph Na-towitz. He then joined the la-boratory of Prof. JosephSadighi at the MassachusettsInstitute of Technology wherehe studied oxidation catalysis.He received his PhD in 2007,and subsequently accepted a
post-doctoral position at Los Alamos National Laboratorywhere he currently resides. His current research interests includethe formation of molecular catalysts for amine borane dehydro-genation.
R. Tom Baker
R. Tom Baker received hisBSc degree from UBC in1975 and his PhD from UCLAin 1980 with M. FrederickHawthorne. After a postdoc-toral stint with Philip S. Skellat Penn State, he joined Du-Pont Central Research in Wil-mington, DE, where he appliedinorganic and organometallicchemistry and homogeneouscatalysis to the nylon, fluoro-products, and titanium dioxidebusinesses. He joined theChemistry Division at LosAlamos National Laboratory
in 1996 and worked on multifunctional catalysis approaches tolow-temperature hydrocarbon functionalization and chemicalhydrogen storage. In 2008, he became a chemistry professor atUniversity of Ottawa and the director of the Centre for Cata-lysis Research and Innovation.
This journal is �c The Royal Society of Chemistry 2009 Chem. Soc. Rev., 2009, 38, 279–293 | 279
CRITICAL REVIEW www.rsc.org/csr | Chemical Society Reviews
2 Annual Energy Outlook 2008 (Revised Early Release) http://www.eia.doe.gov/oiaf/aeo/index.html.
3 Eurostat: Energy, transport and environment indicators http://epp.eurostat.ec.europa.eu/.
4 F. X. Han, J. S. Lindner and C. Wang,Naturwissenschaften, 2007,94, 170; A. Yamasaki, J. Chem. Eng. Jpn., 2003, 36, 361.
5 S. Satyapal, J. Petrovic, C. Read, G. Thomas and G. Ordaz,Catal. Today, 2007, 120, 246.
6 A. Boudghene Stambouli and E. Traversa, Renewable SustainableEnergy Rev., 2002, 6, 297.
7 F. H. Stephens, V. Pons and R. T. Baker, Dalton Trans., 2007,2613; T. B. Marder, Angew. Chem., Int. Ed., 2007, 46, 8116;H. W. Langmi and G. S. McGrady,Coord. Chem. Rev., 2007, 251,925.
8 http://www.gm.com/explore/technology/news/2007/fuel_cells/.9 http://automobiles.honda.com/fcx-clarity/.10 A. W. C. van den Berg and C. O. Arean, Chem. Commun., 2008,
668.11 G. G. Tibbetts, G. P. Meisner and C. H. Olk, Carbon, 2001, 39,
2291.12 J. Dong, X. Wang, H. Xu, Q. Zhao and J. Li, Int. J. Hydrogen
Energy, 2007, 32, 4998.13 Z. Yang, Y. Xia and R. Mokaya, J. Am. Chem. Soc., 2007, 129,
1673.14 P. M. Budd, A. Butler, J. Selbie, K. Mahmood, N. B. McKeown,
B. Ghanem, K. Msayib, D. Book and A. Walton, Phys. Chem.Chem. Phys., 2007, 9, 1802; N. B. McKeown and P. M. Budd,Chem. Soc. Rev., 2006, 35, 675.
15 J.-Y. Lee, C. D. Wood, D. Bradshaw, M. J. Rosseinsky andA. I. Cooper, Chem. Commun., 2006, 2670.
16 Two recent reviews: J. L. C. Rowsell and O. M. Yaghi, Angew.Chem., Int. Ed., 2005, 44, 4670; D. J. Collins and H.-C. Zhou,J. Mater. Chem., 2007, 17, 3154.
17 A. C. Sudik, A. R. Millward, N. W. Ockwig, A. P. Cote, J. Kimand O. M. Yaghi, J. Am. Chem. Soc., 2005, 127, 7110.
18 Y. Li and R. T. Yang, J. Phys. Chem. B, 2006, 110, 17175.
19 Y. Li and R. T. Yang, J. Am. Chem. Soc., 2006, 128, 726.20 A. D. Lueking and R. T. Yang, Appl. Catal., A, 2004, 265, 259.21 S. Orimo, Y. Nakamori, J. R. Eliseo, A. Zuttel and C. M. Jensen,
Chem. Rev., 2007, 107, 4111.22 P. Chen, Z. Xiong, J. Luo, J. Lin and K. L. Tan, Nature, 2002,
420, 302.23 E. Ronnebro and E. H. Majzoub, J. Phys. Chem. B, 2007, 111,
12045.24 J. Yang, A. Sudik, D. J. Siegel, D. Halliday, A. Drews,
R. O. Carter, III, C. Wolverton, G. J. Lewis, J. W. A. Sachtler,J. J. Low, S. A. Faheem, D. A. Lesch and V. Ozolins, Angew.Chem., Int. Ed., 2008, 47, 882; A. Sudik, J. Yang, D. Halliday andC. Wolverton, J. Phys. Chem. C, 2008, 112, 4384.
25 G. Soloveichik, J.-H. Her, P. W. Stephens, Y. Gao,J. Rijssenbeek, M. Andrus and J.-C. Zhao, Inorg. Chem., 2008,47, 4290.
26 Some representative publications: Z. L. Xiao, R. H. Hauge andJ. L. Margrave, Inorg. Chem., 1993, 32, 642; H.-J. Himmel,L. Manceron, A. J. Downs and P. Pullumbi, Angew. Chem., Int.Ed., 2002, 41, 796; H.-J. Himmel, L. Manceron, A. J. Downs andP. Pullumbi, J. Am. Chem. Soc., 2002, 124, 4448; A. Kohn,H.-J. Himmel and B. Gaertner, Chem.–Eur. J., 2003, 9, 3909.
27 G. H. Spikes, J. C. Fettinger and P. P. Power, J. Am. Chem. Soc.,2005, 127, 12232; Y. Peng, B. D. Ellis, X. Wang and P. P. Power,J. Am. Chem. Soc., 2008, 130, 12268.
28 O. Ciobanu, P. Roquette, S. Leingang, H. Wadepohl, J. Mautzand H.-J. Himmel, Eur. J. Inorg. Chem., 2007, 4530.
29 G. D. Frey, V. Lavallo, B. Donnadieu, W. W. Schoeller andG. Bertrand, Science, 2007, 316, 439.
30 G. C. Welch, R. R. San Juan, J. D. Masuda and D. W. Stephan,Science, 2006, 314, 1124; Y. Guo and S. Li, Inorg. Chem., 2008,47, 6212.
31 G. C. Welch and D. W. Stephan, J. Am. Chem. Soc., 2007, 129,1880; P. A. Chase and D. W. Stephan, Angew. Chem., Int. Ed., 2008,47, 7433; S. J. Geier, T. M. Gilbert and D. W. Stephan, J. Am.Chem. Soc., 2008, 130, 12632; T. A. Rokob, A. Hamza, A. Stirling,T. Soos and I. Papai, Angew. Chem., Int. Ed., 2008, 47, 2435.
32 D. Holschumacher, T. Bannenberg, C. G. Hrib, P. G. Jones andM. Tamm, Angew. Chem., Int. Ed., 2008, 47, 7428.
33 V. Sumerin, F. Schulz, M. Nieger, M. Leskela, T. Repo andB. Rieger, Angew. Chem., Int. Ed., 2008, 47, 6001; V. Sumerin,F. Schulz, M. Atsumi, C. Wang, M. Nieger, M. Leskela, T. Repo,P. Pyykko and B. Rieger, J. Am. Chem. Soc., 2008, 130, 14117.
34 S. Hodoshima, H. Arai, S. Takaiwa and Y. Saito, Int. J. Hydro-gen Energy, 2003, 28, 1255.
35 G. P. Pez, A. R. Scott, A. C. Cooper and H. Cheng, US Pat., 7101 530, 2006; G. P. Pez, A. R. Scott, A. C. Cooper, H. Cheng,F. C. Wilhelm and A. H. Abdourazak, US Pat., 7 351 395, 2008;A. Moores, M. Poyatos, Y. Luo and R. H. Crabtree, New J.Chem., 2006, 30, 1675; E. Clot, O. Eisenstein and R. H. Crabtree,Chem. Commun., 2007, 2231.
36 M.-H. Grosjean, M. Zidoune, L. Roue and J.-Y. Huot, Int. J.Hydrogen Energy, 2006, 31, 109.
37 D. E. Schwarz, T. M. Cameron, P. J. Hay, B. L. Scott, W. Tumasand D. L. Thorn, Chem. Commun., 2005, 5919.
38 S. C. Amendola, M. Binder, S. L. Sharp-Goldman, M. T. Kellyand P. J. Petillo, US Pat., 6 534 033, 2003.
39 Estimated $380 million for 1.41 million vehicles in California,USA alone: J. M. Ogden, Int. J. Hydrogen Energy, 1999, 24, 709.
40 While one valence bond structure for ammonia borane wouldplace a formal negative charge on B and a formal positive chargeon N, in spite of charge transfer from N to B, the nitrogenactually carries a net negative charge due to the electronegativitydifference between N and B. R. Hoffmann, J. Chem. Phys., 1964,40, 2474.
41 L. R. Grant and J. E. Flanagan, US Pat., 4 381 206, 1983.42 F. C. Gunderloy, Jr, B. Spielvogel and R. W. Parry, Inorg. Synth.,
1967, 9, 13.43 H. J. Emeleus and F. G. A. Stone, J. Chem. Soc., 1951, 840.44 G. Kodama, R. W. Parry and J. C. Carter, J. Am. Chem. Soc.,
1959, 81, 3534.45 K. C. Nainan and G. E. Ryschkewitsch, Inorg. Nucl. Chem. Lett.,
1970, 6, 765; G. E. Ryschkewitsch, K. C. Nainan, S. R. Miller,L. J. Todd, W. J. Dewkett, M. Grace, H. Beall, M. F. Hawthorneand R. Leyden, Inorg. Synth., 1974, 15, 113.
Scheme 17 Calculated energy of dehydrogenation for 1,2-azabora-
cyclohexane.
This journal is �c The Royal Society of Chemistry 2009 Chem. Soc. Rev., 2009, 38, 279–293 | 291
46 C. W. Yoon and L. G. Sneddon, J. Am. Chem. Soc., 2006, 128,13992.
47 C. E. Nordman and C. Reimann, J. Am. Chem. Soc., 1959, 81,3538.
48 W. V. Hough and J. M. Makhlouf, US Pat., 3 313 603, 1967.49 R. W. Parry, D. R. Schultz and P. R. Girardot, J. Am. Chem.
Soc., 1958, 80, 1.50 J. E. Flanagan, US Pat., 4 166 843, 1979.51 In the original figure of this patent, (6 + n) H2 should be (6 � n)
H2.52 L. V. Titov, M. D. Levicheva and G. N. Dubikhina, Izv. Akad.
Nauk SSSR, Ser. Khim., 1976, 8, 1856.53 D. A. L. Carvalho and N. W. Shust, US Pat., 3 564 561, 1971.54 R. H. Toenikoetter, PhD Thesis, St. Louis Univ., Missouri, 1959;
J. Williams, R. L. Williams and J. C. Wright, J. Chem. Soc., 1963,5816.
55 M. F. Hawthorne, A. R. Pitochelli, R. D. Strahm and J. J. Miller,J. Am. Chem. Soc., 1960, 82, 1825; B. M. Graybill,A. R. Pitochelli andM. F. Hawthorne, Inorg. Chem., 1962, 1, 622.
56 T. Yogo and S. Naka, J. Mater. Sci., 1990, 25, 374.57 M. T. Nguyen, M. H. Matus and D. A. Dixon, Inorg. Chem.,
2007, 46, 7561.58 M. F. Hawthorne, S. S. Jalisatgi and A. Safronov, University of
Missouri-Columbia’s Progress Towards Chemical Hydrogen Sto-rage Using Polyhedral Borane Anion Salts, DoE Hydrogen AnnualProgress Report, 2007 (http://www.hydrogen.energy.gov/pdfs/progress07/iv_b_5d_hawthorne.pdf).
59 H. Noth and H. Beyer, Chem. Ber., 1960, 93, 928.60 For a general review on amine borane synthesis and properties
see: B. Carboni and L. Monnier, Tetrahedron, 1999, 55, 1197.61 M. F. Hawthorne, J. Am. Chem. Soc., 1961, 83, 831.62 M. F. Hawthorne, J. Am. Chem. Soc., 1961, 83, 833.63 A. Staubitz, M. Besora, J. N. Harvey and I. Manners, Inorg.
Chem., 2008, 47, 5910.64 A. R. Siedle, in Annual Reports on NMR Spectroscopy, ed.
G. A. Webb, Academic Press, London, 1988, vol. 20, ch. 2,pp. 205–306; H. Noth, in NMR: Basic Principles and Progress,ed. P. Diehl, E. Fluck and R. Kosfeld, Springer-Verlag, Berlin,1978, vol. 14.
65 E. Framery and M. Vaultier, Heteroat. Chem., 2000, 11, 218.66 H. Beall and C. H. Bushweller, Chem. Rev., 1973, 73, 465;
A. Jerschow, Prog. Nucl. Magn. Reson. Spectrosc., 2005, 46, 63.67 P. A. Storozhenko, R. A. Svitsyn, V. A. Ketsko, A. K. Buryak
and A. V. Ul’yanov, Russ. J. Inorg. Chem. (Transl. of Zh. Neorg.Khim.), 2005, 50, 980.
68 M. Diwan, V. Diakov, E. Shafirovich and A. Varma, Int. J.Hydrogen Energy, 2008, 33, 1135.
69 H. C. Kelly, F. R. Marchelli and M. B. Giutso, Inorg. Chem.,1964, 3, 431; G. E. Ryschkewitsch, J. Am. Chem. Soc., 1960, 82,3290; G. E. Ryschkewitsch and E. R. Birnbaum, J. Phys. Chem.,1961, 65, 1087; G. E. Ryschkewitsch and E. R. Birnbaum, Inorg.Chem., 1965, 4, 575; H. C. Kelly and V. B. Marriott, Inorg.Chem., 1979, 18, 2875; A. D’Ulivo, M. Onor and E. Pitzalis, Anal.Chem., 2004, 76, 6342.
70 M. Chandra and Q. Xu, J. Power Sources, 2006, 159, 855.71 M. Couturier, B. M. Andresen, J. L. Tucker, P. Dube,
S. J. Brenek and J. T. Negri, Tetrahedron Lett., 2001, 42, 2763.72 M. Couturier, J. L. Tucker, B. M. Andresen, P. Dube,
S. J. Brenek and J. T. Negri, Tetrahedron Lett., 2001, 42, 2285.73 M. Couturier, J. L. Tucker, B. M. Andresen, P. Dube and
J. T. Negri, Org. Lett., 2001, 3, 465; M. Couturier,B. M. Andresen, J. B. Jorgensen, J. L. Tucker, F. R. Busch,S. J. Brenek, P. Dube, D. J. am Ende and J. T. Negri,Org. ProcessRes. Dev., 2002, 6, 42.
74 M. Chandra and Q. Xu, J. Power Sources, 2006, 156, 190.75 Q. Xu and M. Chandra, J. Power Sources, 2006, 163, 364.76 T. J. Clark, G. R. Whittell and I. Manners, Inorg. Chem., 2007,
46, 7522.77 P. V. Ramachandran and P. D. Gagare, Inorg. Chem., 2007, 46,
7810.78 S. B. Kalidindi, M. Indirani and B. R. Jagirdar, Inorg. Chem.,
2008, 47, 7424.79 F. Cheng, H. Ma, Y. Li and J. Chen, Inorg. Chem., 2007, 46, 788.80 J.-M. Yan, X.-B. Zhang, S. Han, H. Shioyama and Q. Xu, Angew.
Chem., Int. Ed., 2008, 47, 2287.
81 D. A. Dixon and M. Gutowski, J. Phys. Chem. A, 2005, 109,5129.
82 J. Zhang, S. Zhang and Q. S. Li, J. Mol. Struct. (THEOCHEM),2005, 717, 33; Q. S. Li, J. Zhang and S. Zhang, Chem. Phys. Lett.,2005, 404, 100.
83 M. T. Nguyen, V. S. Nguyen, M. H. Matus, G. Gopakumar andD. A. Dixon, J. Phys. Chem. A, 2007, 111, 679.
84 J. Li, S. M. Kathmann, G. K. Schenter and M. Gutowski,J. Phys. Chem. C, 2007, 111, 3294; D. Jacquemin,E. A. Perpete, V. Wathelet and J.-M. Andre, J. Phys. Chem. A,2004, 108, 9616.
85 M. H.Matus, K. D. Anderson, D. M. Camaioni, S. T. Autrey andD. A. Dixon, J. Phys. Chem. A, 2007, 111, 4411.
86 C. R. Miranda and G. Ceder, J. Chem. Phys., 2007, 126,184703.
87 M. P. Brown, R. W. Heseltine and L. H. Sutcliffe, J. Chem. Soc.A, 1968, 612.
88 O. T. Beachley, Inorg. Chem., 1967, 6, 870; M. E. Bowden, I. W.M. Brown, G. J. Gainsford and H. Wong, Inorg. Chim. Acta,2008, 361, 2147.
89 M. G. Hu, R. A. Geanangel and W. W. Wendlandt, Thermochim.Acta, 1978, 23, 249; R. A. Geanangel and W. W. Wendlandt,Thermochim. Acta, 1985, 86, 375; V. Sit, R. A. Geanangel andW. W. Wendlandt, Thermochim. Acta, 1987, 113, 379; G. Wolf,J. Baumann, F. Baitalow and F. P. Hoffmann, Thermochim. Acta,2000, 343, 19; F. Baitalow, J. Baumann, G. Wolf, K. Jaenicke-Roßler and G. Leitner, Thermochim. Acta, 2002, 391, 159;J. Baumann, F. Baitalow and G. Wolf, Thermochim. Acta,2005, 430, 9.
90 A good indication of whether pure boron nitride has beenobtained is the IR spectrum: often, authors cite WAXS data asproof, where BN can indeed be identified, but some N–H bondsremain, which can be identified by a prominent N–H stretch bandaround 3600 cm�1.
91 Both compounds were confirmed as volatile products in matrixisolation studies: J. D. Carpenter and B. S. Ault, Chem. Phys.Lett., 1992, 197, 171.
92 P. M. Kuznesof, D. F. Shriver and F. E. Stafford, J. Am. Chem.Soc., 1968, 90, 2557.
93 A. C. Stowe, W. J. Shaw, J. C. Linehan, B. Schmid and T. Autrey,Phys. Chem. Chem. Phys., 2007, 9, 1831; M. Bowden, T. Autrey,I. Brown and M. Ryan, Curr. Appl. Phys., 2008, 8, 498.
94 The thermal dehydrogenation of borazine to form boron nitridehas elicited considerable interest due to the material properties ofboron nitride. While this expands the chemical knowledge offormally the third dehydrogenation step of ammonia borane, thisis of no interest for hydrogen storage purposes, as firstly, borazineis a fuel cell poison and secondly, formation of boron nitrideas a thermodynamically extremely stable product makesrecycling difficult. Readers who are interested in this aspect ofammonia borane chemistry are referred to, for example:A. W. Laubengayer, P. C. Moews, Jr and R. F. Porter, J. Am.Chem. Soc., 1961, 83, 1337; P. J. Fazen, J. S. Beck, A. T. Lynch,E. E. Remsen and L. G. Sneddon, Chem. Mater., 1990, 2, 96;P. J. Fazen, E. E. Remsen, J. S. Beck, P. J. Carroll, A. R. McGhieand L. G. Sneddon, Chem. Mater., 1995, 7, 1942; D.-P. Kim,K.-T. Moon, J.-G. Kho, J. Economy, C. Gervais andF. Babonneau, Polym. Adv. Technol., 1999, 10, 702.
95 S. De Benedetto, M. Carewska, C. Cento, P. Gislon, M.Pasquali, S. Scaccia and P. P. Prosini, Thermochim. Acta, 2006,441, 184.
96 A. Gutowska, L. Li, Y. Shin, C. M. Wang, X. S. Li, J. C. Linehan,R. S. Smith, B. D. Kay, B. Schmid, W. Shaw, M. Gutowski andT. Autrey, Angew. Chem., Int. Ed., 2005, 44, 3578.
97 A. M. Feaver, S. Sepehri, P. J. Shamberger, A. C. Stowe,T. Autrey and G. Cao, J. Phys. Chem. B, 2007, 111, 7469.
98 J. S. Wang and R. A. Geanangel, Inorg. Chim. Acta, 1988, 148,185; W. J. Shaw, J. C. Linehan, N. K. Szymczak,D. J. Heldenbrandt, C. Yonker, D. M. Camaioni, R. T. Bakerand T. Autrey, Angew. Chem., Int. Ed., 2008, 47, 7493.
99 M. E. Bluhm, M. G. Bradley, R. Butterick III, U. Kusari andL. G. Sneddon, J. Am. Chem. Soc., 2006, 128, 7748.
100 F. H. Stephens, R. T. Baker, M. Hernandez-Matus, D. J. Grantand D. A. Dixon, Prepr. Pap. - Am. Chem. Soc., Div. Fuel Chem.,2006, 51, 573.
292 | Chem. Soc. Rev., 2009, 38, 279–293 This journal is �c The Royal Society of Chemistry 2009
101 L. G. Sneddon, Amineborane Hydrogen Storage - New Methodsfor Promoting Amineborane Dehydrogenation/Regeneration Reac-tions, DoE Hydrogen Annual Progress Report, 2007 (http://www.hydrogen.energy.gov/pdfs/progress07/iv_b_5e_sneddon.pdf).
102 L. G. Sneddon, Amineborane Based Chemical Hydrogen Storage,DoE Hydrogen Annual Merit Review, 2007 (http://www.hydrogen.energy.gov/pdfs/review07/st_27_sneddon.pdf).
103 Y. D. Blum and R. M. Laine, US Pat., 4 801 439, 1989.104 I. G. Green, K. M. Johnson and B. P. Roberts, J. Chem. Soc.,
Perkin Trans. 2, 1989, 1963.105 Y. Jiang and H. Berke, Chem. Commun., 2007, 3571.106 C. A. Jaska, K. Temple, A. J. Lough and I. Manners, Chem.
Commun., 2001, 962; C. A. Jaska, K. Temple, A. J. Lough andI. Manners, J. Am. Chem. Soc., 2003, 125, 9424; C. A. Jaska andI. Manners, J. Am. Chem. Soc., 2004, 126, 9776.
107 Y. Chen, J. L. Fulton, J. C. Linehan and T. Autrey, J. Am. Chem.Soc., 2005, 127, 3254; J. L. Fulton, J. C. Linehan, T. Autrey,M. Balasubramanian, Y. Chen and N. K. Szymczak, J. Am.Chem. Soc., 2007, 129, 11936.
108 R. J. Keaton, J. M. Blacquiere and R. T. Baker, J. Am. Chem.Soc., 2007, 129, 1844.
110 T. J. Clark, C. A. Russell and I. Manners, J. Am. Chem. Soc.,2006, 128, 9582.
111 D. Pun, E. Lobkovsky and P. J. Chirik, Chem. Commun., 2007,3297.
112 POCOP is k3-2,6-[OP(t-Bu)2]2C6H3.113 M. C. Denney, V. Pons, T. J. Hebden, D. M. Heinekey and
K. I. Goldberg, J. Am. Chem. Soc., 2006, 128, 12048.114 K. W. Boddeker, S. G. Shore and R. K. Bunting, J. Am. Chem.
Soc., 1966, 88, 4396.115 A. Staubitz, A. P. Soto and I. Manners, Angew. Chem., Int. Ed.,
2008, 47, 6212.
116 Y. Luo and K. Ohno, Organometallics, 2007, 26, 3597.117 A. Paul and C. B. Musgrave, Angew. Chem., Int. Ed., 2007, 46,
8153.118 X. Yang and M. B. Hall, J. Am. Chem. Soc., 2008, 130, 1798.119 S. Hausdorf, F. Baitalow, G. Wolf and F. O. R. L. Mertens, Int.
J. Hydrogen Energy, 2008, 33, 608.120 F. M. Taylor and J. Dewing, US Pat., 3 103 417, 1963.121 K. C. Ott, R. T. Baker, A. K. Burrell, B. L. Davis, H. V.
K. Diyabalanage, J. C. Gordon, C. W. Hamilton, M. Inbody,K. K. Jonietz, R. J. Keaton, V. Pons, T. A. Semelsberger,R. Shrestha, F. H. Stephens, D. L. Thorn and W. Tumas,Chemical Hydrogen Storage Research at Los Alamos NationalLaboratory, DoE Hydrogen Annual Progress Report, 2007 (http://www.hydrogen.energy.gov/pdfs/progress07/iv_b_5g_ott.pdf).
122 Z. Xiong, C. K. Yong, G. Wu, P. Chen, W. Shaw, A. Karkamkar,T. Autrey, M. O. Jones, S. R. Johnson, P. P. Edwards and W. I.F. David, Nat. Mater., 2008, 7, 138.
123 A shorter bond distance on its own cannot per se serve as prooffor a stronger bond. For a discussion see for example: F. Bessacand G. Frenking, Inorg. Chem., 2006, 45, 6956.
124 H. V. K. Diyabalanage, R. P. Shrestha, T. A. Semelsberger,B. L. Scott, M. E. Bowden, B. L. Davis and A. K. Burrell, Angew.Chem., Int. Ed., 2007, 46, 8995.
125 A. J. Arduengo and D. A. Dixon,Main Group Element and OrganicChemistry for Hydrogen Storage and Activation, DoE HydrogenProgram Review, 2008 (http://www.hydrogen.energy.gov/pdfs/review08/st_9_dixon.pdf); K. Goldberg and M. Heinekey, Solutionsfor Chemical Hydrogen Storage: Dehydrogenation of B–N Bonds,DoE Hydrogen Program Review, 2008 (http://www.hydrogen.energy.gov/pdfs/review08/st_10_goldberg.pdf).
126 E. R. Abbey, L. N. Zakharov and S.-Y. Liu, J. Am. Chem. Soc.,2008, 130, 7250; E. R. Abbey, J. T. Jenkins, L. N. Zakharov andS.-Y. Liu,Org. Lett., 2007, 9, 4905; M. Scheideman, G. Wang andE. Vedejs, J. Am. Chem. Soc., 2008, 130, 8669.
127 C. A. Jaska and I. Manners, J. Am. Chem. Soc., 2004, 126, 2698;D. Chen and J. Klankermayer, Chem. Commun., 2008, 2130.
This journal is �c The Royal Society of Chemistry 2009 Chem. Soc. Rev., 2009, 38, 279–293 | 293