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Properties and interactions – melting point of tri­bromo­benzene isomers

Single crystals of isomeric 1,2,3-tri­bromo­benzene (123TBB), 1,2,4-tri­bromo­benzene (124TBB) and 1,3,5-tri­bromo­benzene (135TBB) have been grown from different solvents and their structures determined by X-ray diffraction at 100, 200 and 270 K. The melting-point differences of ca 40 K between 135...

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Detalles Bibliográficos
Autores principales: Bujak, Maciej, Podsiadło, Marcin, Katrusiak, Andrzej
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8500239/
http://dx.doi.org/10.1107/S2052520621006399
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author Bujak, Maciej
Podsiadło, Marcin
Katrusiak, Andrzej
author_facet Bujak, Maciej
Podsiadło, Marcin
Katrusiak, Andrzej
author_sort Bujak, Maciej
collection PubMed
description Single crystals of isomeric 1,2,3-tri­bromo­benzene (123TBB), 1,2,4-tri­bromo­benzene (124TBB) and 1,3,5-tri­bromo­benzene (135TBB) have been grown from different solvents and their structures determined by X-ray diffraction at 100, 200 and 270 K. The melting-point differences of ca 40 K between 135TBB, 123TBB and 124TBB have been correlated with the molecular symmetry and packing preferences in the crystal, as well as with the main types of intermolecular halogen interactions, i.e. Br⋯Br, Br⋯C (Br⋯π) and Br⋯H. The relationship between symmetry and melting point in Carnelley’s rule has been extended to the accessibility of terminal atoms for the formation of intermolecular interactions, their occurrences and distribution, and the close packing. The electrostatic potential mapped on molecular surfaces demonstrates that in more symmetric molecules the more evenly distributed substituents are more accessible and form more optimum intermolecular interactions.
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spelling pubmed-85002392021-10-20 Properties and interactions – melting point of tri­bromo­benzene isomers Bujak, Maciej Podsiadło, Marcin Katrusiak, Andrzej Acta Crystallogr B Struct Sci Cryst Eng Mater Research Papers Single crystals of isomeric 1,2,3-tri­bromo­benzene (123TBB), 1,2,4-tri­bromo­benzene (124TBB) and 1,3,5-tri­bromo­benzene (135TBB) have been grown from different solvents and their structures determined by X-ray diffraction at 100, 200 and 270 K. The melting-point differences of ca 40 K between 135TBB, 123TBB and 124TBB have been correlated with the molecular symmetry and packing preferences in the crystal, as well as with the main types of intermolecular halogen interactions, i.e. Br⋯Br, Br⋯C (Br⋯π) and Br⋯H. The relationship between symmetry and melting point in Carnelley’s rule has been extended to the accessibility of terminal atoms for the formation of intermolecular interactions, their occurrences and distribution, and the close packing. The electrostatic potential mapped on molecular surfaces demonstrates that in more symmetric molecules the more evenly distributed substituents are more accessible and form more optimum intermolecular interactions. International Union of Crystallography 2021-07-24 /pmc/articles/PMC8500239/ http://dx.doi.org/10.1107/S2052520621006399 Text en © Maciej Bujak et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Papers
Bujak, Maciej
Podsiadło, Marcin
Katrusiak, Andrzej
Properties and interactions – melting point of tri­bromo­benzene isomers
title Properties and interactions – melting point of tri­bromo­benzene isomers
title_full Properties and interactions – melting point of tri­bromo­benzene isomers
title_fullStr Properties and interactions – melting point of tri­bromo­benzene isomers
title_full_unstemmed Properties and interactions – melting point of tri­bromo­benzene isomers
title_short Properties and interactions – melting point of tri­bromo­benzene isomers
title_sort properties and interactions – melting point of tri­bromo­benzene isomers
topic Research Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8500239/
http://dx.doi.org/10.1107/S2052520621006399
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