Artículo
Abstract:
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.
Registro:
| Documento: | Artículo |
| Título: | Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes |
| Autor: | Fonrouge, A.; Cecchi, F.; Alborés, P.; Baggio, R.; Cukiernik, F.D. |
| Filiación: | Departamento de Qúmica Inorgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina Departamento de F́sica, Comisión Nacional de Enerǵa Atómica, Buenos Aires, Argentina |
| Palabras 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 |
| Año: | 2013 |
| Volumen: | 69 |
| Número: | 2 |
| Página de inicio: | 204 |
| Página de fin: | 208 |
| DOI: | http://dx.doi.org/10.1107/S0108270113002485 |
| Título revista: | Acta Crystallographica Section C: Crystal Structure Communications |
| Título revista abreviado: | Acta Crystallogr Sect C Cryst Struct Commun |
| ISSN: | 01082701 |
| CODEN: | ACSCE |
| PDF: | https://bibliotecadigital.exactas.uba.ar/download/paper/paper_01082701_v69_n2_p204_Fonrouge.pdf |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01082701_v69_n2_p204_Fonrouge |
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Citas:
---------- APA ----------
Fonrouge, A., Cecchi, F., Alborés, P., Baggio, R. & Cukiernik, F.D. (2013) . Relative influence of noncovalent interactions on the melting points of a homologous series of 1,2-dibromo- 4,5-dialkoxybenzenes. Acta Crystallographica Section C: Crystal Structure Communications, 69(2), 204-208.http://dx.doi.org/10.1107/S0108270113002485
---------- CHICAGO ----------
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" . Acta Crystallographica Section C: Crystal Structure Communications 69, no. 2 (2013) : 204-208.http://dx.doi.org/10.1107/S0108270113002485
---------- MLA ----------
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" . Acta Crystallographica Section C: Crystal Structure Communications, vol. 69, no. 2, 2013, pp. 204-208.http://dx.doi.org/10.1107/S0108270113002485
---------- VANCOUVER ----------
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. Acta Crystallogr Sect C Cryst Struct Commun. 2013;69(2):204-208.http://dx.doi.org/10.1107/S0108270113002485
