Stabilization of hydrogen peroxide by hydrogen bonding in the crystal structure of 2-aminobenzimidazole perhydrate

Andrei V. Churakov; Dmitry A. Grishanov; Alexander G. Medvedev; Alexey A. Mikhaylov; Mikhail V. Vener; Mger A. Navasardyan; Tatiana A. Tripol'Skaya; Ovadia Lev; Petr V. Prikhodchenko

doi:10.1039/d0ce00096e

Stabilization of hydrogen peroxide by hydrogen bonding in the crystal structure of 2-aminobenzimidazole perhydrate

Andrei V. Churakov, Dmitry A. Grishanov, Alexander G. Medvedev, Alexey A. Mikhaylov, Mikhail V. Vener, Mger A. Navasardyan, Tatiana A. Tripol'Skaya, Ovadia Lev^*, Petr V. Prikhodchenko

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

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.

Original language	American English
Pages (from-to)	2866-2872
Number of pages	7
Journal	CrystEngComm
Volume	22
Issue number	16
DOIs	https://doi.org/10.1039/d0ce00096e
State	Published - 28 Apr 2020

Bibliographical note

Funding Information:
The authors acknowledge the Russian Foundation for Basic Research for providing the financial support (grants 17-03-00762, 18-33-20211, 18-29-19119, 18-03-00973 and 18-03-01107). The X-ray diffraction study was performed at the Centre of Shared Equipment of IGIC RAS within the State Assignment on Fundamental Research to the Kurnakov Institute of General and Inorganic Chemistry. AGM thanks the Council on Grants of the President of the Russian Federation (MK-6475.2018.3). OL acknowledges the Israel Science Foundation (grant number 1215/19).

Publisher Copyright:
This journal is © The Royal Society of Chemistry.

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@article{386789fd55284b3eb8845275ca1a8b79,

title = "Stabilization of hydrogen peroxide by hydrogen bonding in the crystal structure of 2-aminobenzimidazole perhydrate",

abstract = "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.",

author = "Churakov, {Andrei V.} and Grishanov, {Dmitry A.} and Medvedev, {Alexander G.} and Mikhaylov, {Alexey A.} and Vener, {Mikhail V.} and Navasardyan, {Mger A.} and Tripol'Skaya, {Tatiana A.} and Ovadia Lev and Prikhodchenko, {Petr V.}",

note = "Funding Information: The authors acknowledge the Russian Foundation for Basic Research for providing the financial support (grants 17-03-00762, 18-33-20211, 18-29-19119, 18-03-00973 and 18-03-01107). The X-ray diffraction study was performed at the Centre of Shared Equipment of IGIC RAS within the State Assignment on Fundamental Research to the Kurnakov Institute of General and Inorganic Chemistry. AGM thanks the Council on Grants of the President of the Russian Federation (MK-6475.2018.3). OL acknowledges the Israel Science Foundation (grant number 1215/19). Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

month = apr,

day = "28",

doi = "10.1039/d0ce00096e",

language = "American English",

volume = "22",

pages = "2866--2872",

journal = "CrystEngComm",

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publisher = "Royal Society of Chemistry",

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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 - Funding Information: The authors acknowledge the Russian Foundation for Basic Research for providing the financial support (grants 17-03-00762, 18-33-20211, 18-29-19119, 18-03-00973 and 18-03-01107). The X-ray diffraction study was performed at the Centre of Shared Equipment of IGIC RAS within the State Assignment on Fundamental Research to the Kurnakov Institute of General and Inorganic Chemistry. AGM thanks the Council on Grants of the President of the Russian Federation (MK-6475.2018.3). OL acknowledges the Israel Science Foundation (grant number 1215/19). 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.

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U2 - 10.1039/d0ce00096e

DO - 10.1039/d0ce00096e

M3 - Article

AN - SCOPUS:85084116631

SN - 1466-8033

VL - 22

SP - 2866

EP - 2872

JO - CrystEngComm

JF - CrystEngComm

IS - 16

ER -

Stabilization of hydrogen peroxide by hydrogen bonding in the crystal structure of 2-aminobenzimidazole perhydrate

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