TY - JOUR
T1 - Stabilization of hydrogen peroxide by hydrogen bonding in the crystal structure of 2-aminobenzimidazole perhydrate
AU - Churakov, Andrei V.
AU - Grishanov, Dmitry A.
AU - Medvedev, Alexander G.
AU - Mikhaylov, Alexey A.
AU - Vener, Mikhail V.
AU - Navasardyan, Mger A.
AU - Tripol'Skaya, Tatiana A.
AU - Lev, Ovadia
AU - Prikhodchenko, Petr V.
N1 - Publisher Copyright:
This journal is © The Royal Society of Chemistry.
PY - 2020/4/28
Y1 - 2020/4/28
N2 - 2-Aminobenzimidazole hemiperoxosolvate 2(C7H7N3)·H2O2 was synthesized and studied by single crystal X-ray analysis and periodic (solid-state) DFT calculations. The obtained compound, after urea and melamine peroxosolvates, is the third example of an H2O2 crystalline adduct stabilized with the maximum possible number of hydrogen bonds formed by one hydrogen peroxide molecule-2 H-bonds as proton donors and 4 as acceptors. Due to the small size of the hydrogen peroxide molecule, its hydrogen bonding energy contributes the maximal impact and determines the relative value of the hydrogen bonding energy of the peroxosolvate crystal and can be suggested as an energetic criterion of perhydrate stability. The total energy of the 6 hydrogen bonds formed by one hydrogen peroxide molecule in all three compounds (∼140-∼170 kJ mol-1) was calculated and compared to the corresponding values for crystalline hydrogen peroxide and l-serine peroxosolvate. The total energy of the 4 hydrogen bonds of hydrogen peroxide molecule in crystalline H2O2 and l-serine peroxosolvate (150 and 113 kJ mol-1, respectively) was evaluated by solid-state DFT calculations.
AB - 2-Aminobenzimidazole hemiperoxosolvate 2(C7H7N3)·H2O2 was synthesized and studied by single crystal X-ray analysis and periodic (solid-state) DFT calculations. The obtained compound, after urea and melamine peroxosolvates, is the third example of an H2O2 crystalline adduct stabilized with the maximum possible number of hydrogen bonds formed by one hydrogen peroxide molecule-2 H-bonds as proton donors and 4 as acceptors. Due to the small size of the hydrogen peroxide molecule, its hydrogen bonding energy contributes the maximal impact and determines the relative value of the hydrogen bonding energy of the peroxosolvate crystal and can be suggested as an energetic criterion of perhydrate stability. The total energy of the 6 hydrogen bonds formed by one hydrogen peroxide molecule in all three compounds (∼140-∼170 kJ mol-1) was calculated and compared to the corresponding values for crystalline hydrogen peroxide and l-serine peroxosolvate. The total energy of the 4 hydrogen bonds of hydrogen peroxide molecule in crystalline H2O2 and l-serine peroxosolvate (150 and 113 kJ mol-1, respectively) was evaluated by solid-state DFT calculations.
UR - http://www.scopus.com/inward/record.url?scp=85084116631&partnerID=8YFLogxK
U2 - 10.1039/d0ce00096e
DO - 10.1039/d0ce00096e
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AN - SCOPUS:85084116631
SN - 1466-8033
VL - 22
SP - 2866
EP - 2872
JO - CrystEngComm
JF - CrystEngComm
IS - 16
ER -