Abstract
Liquid Organic Hydrogen Carriers are substances that store hydrogen by reversible hydrogenation of aromatic compounds. A major advantage is the fact that they enable the safe and dense storage of large amounts of hydrogen. Nitrogen-containing heterocycles, particularly with five-membered rings, have demonstrated the advantage of lower heats of reaction for dehydrogenation compared to homocyclic systems. In this work, 6,7-benzindole and its hydrogenated form, dodecahydro-6,7–benzindole, have been analyzed regarding their thermodynamic properties. The results have been obtained via high-precision combustion calorimetry and accompanied by quantum-chemical calculations to validate the results. The enthalpy of reaction for dehydrogenation has been determined as ΔrHmo(gas) = +348.9 ± 3.5 kJ·mol−1 in the gas phase and ΔrHmo(liq) = +325.7 ± 3.7 kJ·mol−1 in the liquid phase (ΔrHmo(gas) = +58.2 ± 0.6 kJ·molH2–1 and ΔrHmo(liq) = +54.3 ± 0.6 kJ·molH2–1, respectively). This reaction enthalpy is similar to values for other heterocyclic systems like indole and about 11 kJ·molH2–1 lower than that of homocyclic systems, such as perhydro dibenzyl toluene. As a consequence, it can be expected that the temperature needed thermodynamically to enable hydrogen release from dodecahydro-6,7–benzindole will be lower than for the dehydrogenation of perhydro dibenzyl toluene.
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