A Comparison of Hydrogen Release Kinetics from 5- and 6-membered 1,2-BN-cycloalkanes

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 2

PMID 35497319

Authors

Zachary X Giustra

Gang Chen

Monica Vasiliu

Abhijeet Karkamkar

Tom Autrey

David A Dixon

Shih-Yuan Liu

Affiliations

Soon will be listed here.

Abstract

The reaction order and Arrhenius activation parameters for spontaneous hydrogen release from cyclic amine boranes, , BN-cycloalkanes, were determined for 1,2-BN-cyclohexane (1) and 3-methyl-1,2-BN-cyclopentane (2) in tetraglyme. Computational analysis identified a mechanism involving catalytic substrate activation by a ring-opened form of 1 or 2 as being consistent with experimental observations.

References

Chen G, Zakharov L, Bowden M, Karkamkar A, Whittemore S, Garner 3rd E . Bis-BN cyclohexane: a remarkably kinetically stable chemical hydrogen storage material. J Am Chem Soc. 2014; 137(1):134-7. DOI: 10.1021/ja511766p. View

Staubitz A, Besora M, Harvey J, Manners I . Computational analysis of amine-borane adducts as potential hydrogen storage materials with reversible hydrogen uptake. Inorg Chem. 2008; 47(13):5910-8. DOI: 10.1021/ic800344h. View

Wright W, Berkeley E, Alden L, Baker R, Sneddon L . Transition metal catalysed ammonia-borane dehydrogenation in ionic liquids. Chem Commun (Camb). 2011; 47(11):3177-9. DOI: 10.1039/c0cc05408a. View

Luo W, Zakharov L, Liu S . 1,2-BN cyclohexane: synthesis, structure, dynamics, and reactivity. J Am Chem Soc. 2011; 133(33):13006-9. DOI: 10.1021/ja206497x. View

Nguyen M, Nguyen V, Matus M, Gopakumar G, Dixon D . Molecular mechanism for H2 release from BH3NH3, including the catalytic role of the Lewis acid BH3. J Phys Chem A. 2007; 111(4):679-90. DOI: 10.1021/jp066175y. View

Staubitz A, Robertson A, Manners I . Ammonia-borane and related compounds as dihydrogen sources. Chem Rev. 2010; 110(7):4079-124. DOI: 10.1021/cr100088b. View

Kumar R, Karkamkar A, Bowden M, Autrey T . Solid-state hydrogen rich boron-nitrogen compounds for energy storage. Chem Soc Rev. 2019; 48(21):5350-5380. DOI: 10.1039/c9cs00442d. View

Hamilton C, Baker R, Staubitz A, Manners I . B-N compounds for chemical hydrogen storage. Chem Soc Rev. 2008; 38(1):279-93. DOI: 10.1039/b800312m. View

Kumar A, Ishibashi J, Hooper T, Mikulas T, Dixon D, Liu S . The Synthesis, Characterization and Dehydrogenation of Sigma-Complexes of BN-Cyclohexanes. Chemistry. 2015; 22(1):310-22. PMC: 4818983. DOI: 10.1002/chem.201502986. View

10.

Keaton R, Blacquiere J, Baker R . Base metal catalyzed dehydrogenation of ammonia-borane for chemical hydrogen storage. J Am Chem Soc. 2007; 129(7):1844-5. DOI: 10.1021/ja066860i. View

11.

Gutowska A, Li L, Shin Y, Wang C, Li X, Linehan J . Nanoscaffold mediates hydrogen release and the reactivity of ammonia borane. Angew Chem Int Ed Engl. 2005; 44(23):3578-82. DOI: 10.1002/anie.200462602. View

12.

Matus M, Liu S, Dixon D . Dehydrogenation reactions of cyclic C(2)B(2)N(2)H(12) and C(4)BNH(12) isomers. J Phys Chem A. 2010; 114(7):2644-54. DOI: 10.1021/jp9102838. View

13.

Semelsberger T, Graetz J, Sutton A, Ronnebro E . Engineering Challenges of Solution and Slurry-Phase Chemical Hydrogen Storage Materials for Automotive Fuel Cell Applications. Molecules. 2021; 26(6). PMC: 8003490. DOI: 10.3390/molecules26061722. View

14.

Luo W, Neiner D, Karkamkar A, Parab K, Garner 3rd E, Dixon D . 3-Methyl-1,2-BN-cyclopentane: a promising H2 storage material?. Dalton Trans. 2012; 42(3):611-4. DOI: 10.1039/c2dt31617j. View

15.

Shaw W, Linehan J, Szymczak N, Heldebrant D, Yonker C, Camaioni D . In situ multinuclear NMR spectroscopic studies of the thermal decomposition of ammonia borane in solution. Angew Chem Int Ed Engl. 2008; 47(39):7493-6. DOI: 10.1002/anie.200802100. View

16.

Marder T . Will we soon be fueling our automobiles with ammonia-borane?. Angew Chem Int Ed Engl. 2007; 46(43):8116-8. DOI: 10.1002/anie.200703150. View

17.

Harlow G, Zakharov L, Wu G, Liu S . Thermodynamically Controlled, Dynamic Binding of Diols to a 1,2-BN Cyclohexane Derivative. Organometallics. 2015; 32(22):6650-6653. PMC: 4364440. DOI: 10.1021/om400697r. View

18.

Campbell P, Zakharov L, Grant D, Dixon D, Liu S . Hydrogen storage by boron-nitrogen heterocycles: a simple route for spent fuel regeneration. J Am Chem Soc. 2010; 132(10):3289-91. DOI: 10.1021/ja9106622. View

19.

Rossin A, Peruzzini M . Ammonia-Borane and Amine-Borane Dehydrogenation Mediated by Complex Metal Hydrides. Chem Rev. 2016; 116(15):8848-72. DOI: 10.1021/acs.chemrev.6b00043. View

20.

Stubbs N, Schafer A, Robertson A, Leitao E, Jurca T, Sparkes H . B-Methylated Amine-Boranes: Substituent Redistribution, Catalytic Dehydrogenation, and Facile Metal-Free Hydrogen Transfer Reactions. Inorg Chem. 2015; 54(22):10878-89. DOI: 10.1021/acs.inorgchem.5b01946. View