Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes

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Crystal structures are presented for two members of the homologous series of 1,2-dibromo-4,5-dialkoxybenzenes, viz. those with decyloxy and hexadecyloxy substituents, namely 1,2-dibromo-4,5-bis(decyloxy)benzene, C26H44Br2O2, (II), and 1,2-dibromo-4,5-bis(hexadecyloxy)benzene, C38H68Br2O2, (III). The...

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Autores principales: Fonrouge, A., Cecchi, F., Alborés, P., Baggio, R., Cukiernik, F.D.
Formato: Artículo publishedVersion
Lenguaje:Inglés
Publicado: 2013
Materias:
Aliphatic chains
Crystal stability
Dimethoxybenzene
Halogen bonding
Homologous series
Non-covalent interaction
Van der Waals contacts
Van Der Waals interactions
Benzene
Iodine
Ions
Melting point
Van der Waals forces
Bromine
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_01082701_v69_n2_p204_Fonrouge
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling paperaa:paper_01082701_v69_n2_p204_Fonrouge2023-06-12T16:46:36Z Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes Acta Crystallogr Sect C Cryst Struct Commun 2013;69(2):204-208 Fonrouge, A. Cecchi, F. Alborés, P. Baggio, R. Cukiernik, F.D. Aliphatic chains Crystal stability Dimethoxybenzene Halogen bonding Homologous series Non-covalent interaction Van der Waals contacts Van Der Waals interactions Benzene Iodine Ions Melting point Van der Waals forces Bromine Crystal structures are presented for two members of the homologous series of 1,2-dibromo-4,5-dialkoxybenzenes, viz. those with decyloxy and hexadecyloxy substituents, namely 1,2-dibromo-4,5-bis(decyloxy)benzene, C26H44Br2O2, (II), and 1,2-dibromo-4,5-bis(hexadecyloxy)benzene, C38H68Br2O2, (III). The relative influences which halogen bonding, π- π stacking and van der Waals interactions have on these structures are analysed and the results compared with those already found for the lightest homologue, 1,2-dibromo-4,5- dimethoxybenzene, (I) [Cukiernik, Zelcer, Garland & Baggio (2008). Acta Cryst. C64, o604-o608]. The results confirm that the prevalent interactions stabilizing the structures of (II) and (III) are van der Waals contacts between the aliphatic chains. In the case of (II), weak halogen C - Br ⋯(Br - C) ′ interactions are also present and contribute to the stability of the structure. In the case of (III), van der Waals interactions between the aliphatic chains are almost exclusive, weaker C - Br ⋯ π interactions being the only additional interactions detected. The results are in line with commonly accepted models concerning trends in crystal stability along a homologous series (as measured by their melting points), but the earlier report for n = 1, and the present report for n = 10 and 16, are among the few providing single-crystal information validating the hypothesis. Fil:Cecchi, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Alborés, P. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cukiernik, F.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2013 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion application/pdf eng info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_01082701_v69_n2_p204_Fonrouge
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
language Inglés
orig_language_str_mv eng
topic Aliphatic chains
Crystal stability
Dimethoxybenzene
Halogen bonding
Homologous series
Non-covalent interaction
Van der Waals contacts
Van Der Waals interactions
Benzene
Iodine
Ions
Melting point
Van der Waals forces
Bromine
spellingShingle Aliphatic chains
Crystal stability
Dimethoxybenzene
Halogen bonding
Homologous series
Non-covalent interaction
Van der Waals contacts
Van Der Waals interactions
Benzene
Iodine
Ions
Melting point
Van der Waals forces
Bromine
Fonrouge, A.
Cecchi, F.
Alborés, P.
Baggio, R.
Cukiernik, F.D.
Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
topic_facet Aliphatic chains
Crystal stability
Dimethoxybenzene
Halogen bonding
Homologous series
Non-covalent interaction
Van der Waals contacts
Van Der Waals interactions
Benzene
Iodine
Ions
Melting point
Van der Waals forces
Bromine
description Crystal structures are presented for two members of the homologous series of 1,2-dibromo-4,5-dialkoxybenzenes, viz. those with decyloxy and hexadecyloxy substituents, namely 1,2-dibromo-4,5-bis(decyloxy)benzene, C26H44Br2O2, (II), and 1,2-dibromo-4,5-bis(hexadecyloxy)benzene, C38H68Br2O2, (III). The relative influences which halogen bonding, π- π stacking and van der Waals interactions have on these structures are analysed and the results compared with those already found for the lightest homologue, 1,2-dibromo-4,5- dimethoxybenzene, (I) [Cukiernik, Zelcer, Garland & Baggio (2008). Acta Cryst. C64, o604-o608]. The results confirm that the prevalent interactions stabilizing the structures of (II) and (III) are van der Waals contacts between the aliphatic chains. In the case of (II), weak halogen C - Br ⋯(Br - C) ′ interactions are also present and contribute to the stability of the structure. In the case of (III), van der Waals interactions between the aliphatic chains are almost exclusive, weaker C - Br ⋯ π interactions being the only additional interactions detected. The results are in line with commonly accepted models concerning trends in crystal stability along a homologous series (as measured by their melting points), but the earlier report for n = 1, and the present report for n = 10 and 16, are among the few providing single-crystal information validating the hypothesis.
format Artículo
Artículo
publishedVersion
author Fonrouge, A.
Cecchi, F.
Alborés, P.
Baggio, R.
Cukiernik, F.D.
author_facet Fonrouge, A.
Cecchi, F.
Alborés, P.
Baggio, R.
Cukiernik, F.D.
author_sort Fonrouge, A.
title Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
title_short Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
title_full Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
title_fullStr Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
title_full_unstemmed Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
title_sort relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
publishDate 2013
url http://hdl.handle.net/20.500.12110/paper_01082701_v69_n2_p204_Fonrouge
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