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

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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Detalles Bibliográficos
Autores: Fonrouge, A., Cecchi, F., Alborés, P., Baggio, R., Cukiernik, F.D.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2013
País:Argentina
Institución:Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
Repositorio:Biblioteca Digital (UBA-FCEN)
Idioma:inglés
OAI Identifier:paperaa:paper_01082701_v69_n2_p204_Fonrouge
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_01082701_v69_n2_p204_Fonrouge
Access Level:acceso abierto
Palabra clave: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
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spelling Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenesFonrouge, A.Cecchi, F.Alborés, P.Baggio, R.Cukiernik, F.D.Aliphatic chainsCrystal stabilityDimethoxybenzeneHalogen bondingHomologous seriesNon-covalent interactionVan der Waals contactsVan Der Waals interactionsBenzeneIodineIonsMelting pointVan der Waals forcesBromineCrystal 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.2013info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttp://hdl.handle.net/20.500.12110/paper_01082701_v69_n2_p204_FonrougeActa Crystallogr Sect C Cryst Struct Commun 2013;69(2):204-208reponame:Biblioteca Digital (UBA-FCEN)instname:Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturalesinstacron:UBA-FCENenginfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/2.5/ar2024-05-10T10:42:44Zpaperaa:paper_01082701_v69_n2_p204_FonrougeInstitucionalhttps://digital.bl.fcen.uba.ar/Universidad públicaNo correspondehttps://digital.bl.fcen.uba.ar/cgi-bin/oaiserver.cgiana@bl.fcen.uba.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:18962024-05-10 10:42:45.4Biblioteca Digital (UBA-FCEN) - Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturalesfalse
dc.title.none.fl_str_mv Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
title Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
spellingShingle Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes
Fonrouge, A.
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
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
dc.creator.none.fl_str_mv Fonrouge, A.
Cecchi, F.
Alborés, P.
Baggio, R.
Cukiernik, F.D.
author Fonrouge, A.
author_facet Fonrouge, A.
Cecchi, F.
Alborés, P.
Baggio, R.
Cukiernik, F.D.
author_role author
author2 Cecchi, F.
Alborés, P.
Baggio, R.
Cukiernik, F.D.
author2_role author
author
author
author
dc.subject.none.fl_str_mv 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
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
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.
publishDate 2013
dc.date.none.fl_str_mv 2013
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/20.500.12110/paper_01082701_v69_n2_p204_Fonrouge
url http://hdl.handle.net/20.500.12110/paper_01082701_v69_n2_p204_Fonrouge
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/2.5/ar
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/2.5/ar
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv Acta Crystallogr Sect C Cryst Struct Commun 2013;69(2):204-208
reponame:Biblioteca Digital (UBA-FCEN)
instname:Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
instacron:UBA-FCEN
instname_str Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
instacron_str UBA-FCEN
institution UBA-FCEN
reponame_str Biblioteca Digital (UBA-FCEN)
collection Biblioteca Digital (UBA-FCEN)
repository.name.fl_str_mv Biblioteca Digital (UBA-FCEN) - Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
repository.mail.fl_str_mv ana@bl.fcen.uba.ar
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score 15,81155

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