Br⋯Br and van der Waals interactions along a homologous series: Crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes
The crystalline structures of four homologues of the 1,2-dibromo-4,5-dialkoxybenzene series [Br2C6H2(OCn H2n+1)2 for n = 2, 12, 14 and 18] have been solved by means of single-crystal crystallography. Comparison along the series, including the previously reported n = 10 and n = 16 derivatives, shows...
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todo:paper_20525192_v72_n_p693_Suarez2023-10-03T16:38:56Z Br⋯Br and van der Waals interactions along a homologous series: Crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes Suarez, S.A. Muller, F. Gutiérrez Suburu, M.E. Fonrouge, A. Baggio, R.F. Cukiernik, F.D. 1,2-dibromo-4,5-dialkoxybenzenes chemical crystallography crystal engineering halogen bonds Crystal engineering Crystalline materials Crystallography Single crystals Van der Waals forces 1,2-dibromo-4,5-dialkoxybenzenes Atoms in Molecules Chemical crystallography Crystalline structure Halogen bonds Interchain interactions Structural support Van Der Waals interactions Van der Waals forces Crystal atomic structure The crystalline structures of four homologues of the 1,2-dibromo-4,5-dialkoxybenzene series [Br2C6H2(OCn H2n+1)2 for n = 2, 12, 14 and 18] have been solved by means of single-crystal crystallography. Comparison along the series, including the previously reported n = 10 and n = 16 derivatives, shows a clear metric trend (b and c essentially fixed along the series and a growing linearly with n), in spite of some subtle differences in space groups and/or packing modes. A uniform packing pattern for the aliphatic chains has been found for the n = 12 to 18 homologues, which slightly differs from that of the n = 10 derivative. The crystalline structures of all the higher homologues (n = 10-18) seem to arise from van der Waals interchain interactions and, to a lesser extent, type II Br⋯Br interactions. The dominant role of interchain interactions provides direct structural support for the usual interpretation of melting point trends like that found along this series. Atoms in Molecules (AIM) analysis allows a comparison of the relative magnitude of the interchain and Br⋯Br interactions, an analysis validated by the measured melting enthalpies. © 2016 International Union of Crystallography. Fil:Suarez, S.A. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_20525192_v72_n_p693_Suarez |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
1,2-dibromo-4,5-dialkoxybenzenes chemical crystallography crystal engineering halogen bonds Crystal engineering Crystalline materials Crystallography Single crystals Van der Waals forces 1,2-dibromo-4,5-dialkoxybenzenes Atoms in Molecules Chemical crystallography Crystalline structure Halogen bonds Interchain interactions Structural support Van Der Waals interactions Van der Waals forces Crystal atomic structure |
| spellingShingle |
1,2-dibromo-4,5-dialkoxybenzenes chemical crystallography crystal engineering halogen bonds Crystal engineering Crystalline materials Crystallography Single crystals Van der Waals forces 1,2-dibromo-4,5-dialkoxybenzenes Atoms in Molecules Chemical crystallography Crystalline structure Halogen bonds Interchain interactions Structural support Van Der Waals interactions Van der Waals forces Crystal atomic structure Suarez, S.A. Muller, F. Gutiérrez Suburu, M.E. Fonrouge, A. Baggio, R.F. Cukiernik, F.D. Br⋯Br and van der Waals interactions along a homologous series: Crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes |
| topic_facet |
1,2-dibromo-4,5-dialkoxybenzenes chemical crystallography crystal engineering halogen bonds Crystal engineering Crystalline materials Crystallography Single crystals Van der Waals forces 1,2-dibromo-4,5-dialkoxybenzenes Atoms in Molecules Chemical crystallography Crystalline structure Halogen bonds Interchain interactions Structural support Van Der Waals interactions Van der Waals forces Crystal atomic structure |
| description |
The crystalline structures of four homologues of the 1,2-dibromo-4,5-dialkoxybenzene series [Br2C6H2(OCn H2n+1)2 for n = 2, 12, 14 and 18] have been solved by means of single-crystal crystallography. Comparison along the series, including the previously reported n = 10 and n = 16 derivatives, shows a clear metric trend (b and c essentially fixed along the series and a growing linearly with n), in spite of some subtle differences in space groups and/or packing modes. A uniform packing pattern for the aliphatic chains has been found for the n = 12 to 18 homologues, which slightly differs from that of the n = 10 derivative. The crystalline structures of all the higher homologues (n = 10-18) seem to arise from van der Waals interchain interactions and, to a lesser extent, type II Br⋯Br interactions. The dominant role of interchain interactions provides direct structural support for the usual interpretation of melting point trends like that found along this series. Atoms in Molecules (AIM) analysis allows a comparison of the relative magnitude of the interchain and Br⋯Br interactions, an analysis validated by the measured melting enthalpies. © 2016 International Union of Crystallography. |
| format |
JOUR |
| author |
Suarez, S.A. Muller, F. Gutiérrez Suburu, M.E. Fonrouge, A. Baggio, R.F. Cukiernik, F.D. |
| author_facet |
Suarez, S.A. Muller, F. Gutiérrez Suburu, M.E. Fonrouge, A. Baggio, R.F. Cukiernik, F.D. |
| author_sort |
Suarez, S.A. |
| title |
Br⋯Br and van der Waals interactions along a homologous series: Crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes |
| title_short |
Br⋯Br and van der Waals interactions along a homologous series: Crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes |
| title_full |
Br⋯Br and van der Waals interactions along a homologous series: Crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes |
| title_fullStr |
Br⋯Br and van der Waals interactions along a homologous series: Crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes |
| title_full_unstemmed |
Br⋯Br and van der Waals interactions along a homologous series: Crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes |
| title_sort |
br⋯br and van der waals interactions along a homologous series: crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes |
| url |
http://hdl.handle.net/20.500.12110/paper_20525192_v72_n_p693_Suarez |
| work_keys_str_mv |
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1782024230172360704 |