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Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid
The anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with 4-aminobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate, C(9)H(17)N(2) (+)·C(7)H(6)NO(2) (−) (I)], 3,5-dinitrobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 3,5-dinitrobenzoat...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2016
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778835/ https://www.ncbi.nlm.nih.gov/pubmed/27006813 http://dx.doi.org/10.1107/S205698901600267X |
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author | Smith, Graham Lynch, Daniel E. |
author_facet | Smith, Graham Lynch, Daniel E. |
author_sort | Smith, Graham |
collection | PubMed |
description | The anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with 4-aminobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate, C(9)H(17)N(2) (+)·C(7)H(6)NO(2) (−) (I)], 3,5-dinitrobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 3,5-dinitrobenzoate, C(9)H(17)N(2) (+)·C(7)H(3)N(2)O(6) (−), (II)] and 3,5-dinitrosalicylic acid (DNSA) [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate, C(9)H(17)N(2) (+)·C(7)H(3)N(2)O(7) (−), (III)] have been determined and their hydrogen-bonded structures are described. In both (II) and (III), the DBU cations have a common disorder in three of the C atoms of the six-membered ring moieties [site-occupancy factors (SOF) = 0.735 (3)/0.265 (3) and 0.686 (4)/0.314 (4), respectively], while in (III), there is additional rotational disorder in the DNSA anion, giving two sites (SOF = 0.72/0.28, values fixed) for the phenol group. In the crystals of (I) and (III), the cation–anion pairs are linked through a primary N—H⋯O(carboxyl) hydrogen bond [2.665 (2) and 2.869 (3) Å, respectively]. In (II), the ion pairs are linked through an asymmetric three-centre R (1) (2)(4), N—H⋯O,O′ chelate association. In (I), structure extension is through amine N—H⋯O(carboxyl) hydrogen bonds between the PABA anions, giving a three-dimensional structure. The crystal structures of (II) and (III) are very similar, the cation–anion pairs being associated only through weak C—H⋯O hydrogen bonds, giving in both overall two-dimensional layered structures lying parallel to (001). No π–π ring associations are present in any of the structures. |
format | Online Article Text |
id | pubmed-4778835 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-47788352016-03-22 Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid Smith, Graham Lynch, Daniel E. Acta Crystallogr E Crystallogr Commun Research Communications The anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with 4-aminobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate, C(9)H(17)N(2) (+)·C(7)H(6)NO(2) (−) (I)], 3,5-dinitrobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 3,5-dinitrobenzoate, C(9)H(17)N(2) (+)·C(7)H(3)N(2)O(6) (−), (II)] and 3,5-dinitrosalicylic acid (DNSA) [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate, C(9)H(17)N(2) (+)·C(7)H(3)N(2)O(7) (−), (III)] have been determined and their hydrogen-bonded structures are described. In both (II) and (III), the DBU cations have a common disorder in three of the C atoms of the six-membered ring moieties [site-occupancy factors (SOF) = 0.735 (3)/0.265 (3) and 0.686 (4)/0.314 (4), respectively], while in (III), there is additional rotational disorder in the DNSA anion, giving two sites (SOF = 0.72/0.28, values fixed) for the phenol group. In the crystals of (I) and (III), the cation–anion pairs are linked through a primary N—H⋯O(carboxyl) hydrogen bond [2.665 (2) and 2.869 (3) Å, respectively]. In (II), the ion pairs are linked through an asymmetric three-centre R (1) (2)(4), N—H⋯O,O′ chelate association. In (I), structure extension is through amine N—H⋯O(carboxyl) hydrogen bonds between the PABA anions, giving a three-dimensional structure. The crystal structures of (II) and (III) are very similar, the cation–anion pairs being associated only through weak C—H⋯O hydrogen bonds, giving in both overall two-dimensional layered structures lying parallel to (001). No π–π ring associations are present in any of the structures. International Union of Crystallography 2016-02-20 /pmc/articles/PMC4778835/ /pubmed/27006813 http://dx.doi.org/10.1107/S205698901600267X Text en © Smith and Lynch 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Smith, Graham Lynch, Daniel E. Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title | Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_full | Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_fullStr | Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_full_unstemmed | Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_short | Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_sort | crystal structures of three anhydrous salts of the lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (dbu) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778835/ https://www.ncbi.nlm.nih.gov/pubmed/27006813 http://dx.doi.org/10.1107/S205698901600267X |
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