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Artículo

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

Fonrouge, Ana; Cecchi, FlorenciaIcon ; Alborés, PabloIcon ; Baggio, Ricardo Fortunato; Cukiernik, Fabio DanielIcon
Fecha de publicación: 01/2013
Editorial: Wiley Blackwell Publishing, Inc
Revista: Acta Crystallographica Section C-Crystal Structure Communications
ISSN: 0108-2701
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Química Orgánica

Resumen

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.
Palabras clave: Center-Dot-Br , Crystalline , Halogen
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/727
DOI: http://dx.doi.org/10.1107/S0108270113002485
URL: https://onlinelibrary.wiley.com/doi/epdf/10.1107/S0108270113002485?sentby=iucr
Colecciones
Articulos(INQUIMAE)
Articulos de INST.D/QUIM FIS D/L MATERIALES MEDIOAMB Y ENERGIA
Citación
Fonrouge, Ana; Cecchi, Florencia; Alborés, Pablo; Baggio, Ricardo Fortunato; Cukiernik, Fabio Daniel; Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section C-Crystal Structure Communications; 69; 2; 1-2013; 204-208
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