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Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide

1
Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, Saint Petersburg 199034, Russia
2
Center for X-ray Diffraction Studies, Saint Petersburg State University, Universitetskii Pr., 26, Saint Petersburg 198504, Russia
*
Authors to whom correspondence should be addressed.
Symmetry 2020, 12(4), 637; https://doi.org/10.3390/sym12040637
Received: 31 March 2020 / Revised: 12 April 2020 / Accepted: 14 April 2020 / Published: 17 April 2020
(This article belongs to the Special Issue Symmetry in Quantum and Computational Chemistry)
4-Bromobenzamidrazone reacts with cyclopentanone giving 3-(4-bromophenyl)-5-(4-peroxobutyl)-1,2,4-triazole, which precipitated as pale-yellow crystals during the reaction. The intermolecular noncovalent interactions Br···Br in the single-crystal XRD structure of the peroxo compound were studied theoretically using quantum chemical calculations (ωB97XD/x2c-TZVPPall) and quantum theory of atoms in molecules (QTAIM) analysis. These attractive intermolecular noncovalent interactions Br···Br is type I halogen···halogen contacts and their estimated energy is 2.2–2.5 kcal/mol. These weak interactions are suggested to be one of the driving forces (albeit surely not the main one) for crystallization of the peroxo compound during the reaction and thus its stabilization in the solid state. View Full-Text
Keywords: organic peroxide; triazole; DFT; QTAIM; noncovalent interactions; halogen bonding organic peroxide; triazole; DFT; QTAIM; noncovalent interactions; halogen bonding
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MDPI and ACS Style

Bolotin, D.S.; Il’in, M.V.; Suslonov, V.V.; Novikov, A.S. Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide. Symmetry 2020, 12, 637. https://doi.org/10.3390/sym12040637

AMA Style

Bolotin DS, Il’in MV, Suslonov VV, Novikov AS. Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide. Symmetry. 2020; 12(4):637. https://doi.org/10.3390/sym12040637

Chicago/Turabian Style

Bolotin, Dmitrii S., Mikhail V. Il’in, Vitalii V. Suslonov, and Alexander S. Novikov 2020. "Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide" Symmetry 12, no. 4: 637. https://doi.org/10.3390/sym12040637

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