Cargando…
1-{2-[4-(4-Nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide
The title compound, C(18)H(28)N(5)O(2) (+)·I(−), was observed as a main product in an intended 1:1 reaction between 4-iodonitrobenzene and 1,4-diazabicyclo[2.2.2]octane (DABCO). In the reaction, DABCO undergoes a ring opening to yield a quaternary salt of DABCO and 1-ethyl-4-(4-nitrophenyl)pip...
Autores principales: | , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393262/ https://www.ncbi.nlm.nih.gov/pubmed/22807819 http://dx.doi.org/10.1107/S1600536812024531 |
_version_ | 1782237708641370112 |
---|---|
author | Peuronen, Anssi Lahtinen, Manu |
author_facet | Peuronen, Anssi Lahtinen, Manu |
author_sort | Peuronen, Anssi |
collection | PubMed |
description | The title compound, C(18)H(28)N(5)O(2) (+)·I(−), was observed as a main product in an intended 1:1 reaction between 4-iodonitrobenzene and 1,4-diazabicyclo[2.2.2]octane (DABCO). In the reaction, DABCO undergoes a ring opening to yield a quaternary salt of DABCO and 1-ethyl-4-(4-nitrophenyl)piperazine with an iodide anion. The crystal structure determination was carried out as no crystal structure had been previously reported in the investigations describing the corresponding reaction with 4-chloronitrobenze. Indeed, the crystal structure of the title compound confirms the molecular composition proposed earlier for the analogous chloride salt. The cation conformation is similar to the previously reported dinitro analogue 1-{2-[4-(2,4-dinitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane chloride [Clegg et al. (2004 ▶). Acta Cryst. E60, o291–o293]. The crystal packing is dominated by cation⋯I(−) interactions in addition to weak intermolecular C—H⋯O(2)N and C—H⋯N interactions between the cations. |
format | Online Article Text |
id | pubmed-3393262 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-33932622012-07-17 1-{2-[4-(4-Nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide Peuronen, Anssi Lahtinen, Manu Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(28)N(5)O(2) (+)·I(−), was observed as a main product in an intended 1:1 reaction between 4-iodonitrobenzene and 1,4-diazabicyclo[2.2.2]octane (DABCO). In the reaction, DABCO undergoes a ring opening to yield a quaternary salt of DABCO and 1-ethyl-4-(4-nitrophenyl)piperazine with an iodide anion. The crystal structure determination was carried out as no crystal structure had been previously reported in the investigations describing the corresponding reaction with 4-chloronitrobenze. Indeed, the crystal structure of the title compound confirms the molecular composition proposed earlier for the analogous chloride salt. The cation conformation is similar to the previously reported dinitro analogue 1-{2-[4-(2,4-dinitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane chloride [Clegg et al. (2004 ▶). Acta Cryst. E60, o291–o293]. The crystal packing is dominated by cation⋯I(−) interactions in addition to weak intermolecular C—H⋯O(2)N and C—H⋯N interactions between the cations. International Union of Crystallography 2012-06-02 /pmc/articles/PMC3393262/ /pubmed/22807819 http://dx.doi.org/10.1107/S1600536812024531 Text en © Peuronen and Lahtinen 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Peuronen, Anssi Lahtinen, Manu 1-{2-[4-(4-Nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide |
title | 1-{2-[4-(4-Nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide |
title_full | 1-{2-[4-(4-Nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide |
title_fullStr | 1-{2-[4-(4-Nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide |
title_full_unstemmed | 1-{2-[4-(4-Nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide |
title_short | 1-{2-[4-(4-Nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide |
title_sort | 1-{2-[4-(4-nitrophenyl)piperazin-1-yl]ethyl}-4-aza-1-azoniabicyclo[2.2.2]octane iodide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393262/ https://www.ncbi.nlm.nih.gov/pubmed/22807819 http://dx.doi.org/10.1107/S1600536812024531 |
work_keys_str_mv | AT peuronenanssi 1244nitrophenylpiperazin1ylethyl4aza1azoniabicyclo222octaneiodide AT lahtinenmanu 1244nitrophenylpiperazin1ylethyl4aza1azoniabicyclo222octaneiodide |