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N (2)-(4-Methoxysalicylidene)arginine hemihydrate
The title compound, C(14)H(20)N(4)O(4)·0.5H(2)O [systematic name: (2S)-5-{[amino(iminiumyl)methyl]amino}-2-{[(1Z)-4-methoxy-2-oxidobenzylidene]azaniumyl}pentanoate hemihydrate], has been synthesized by the reaction of l-arginine and 4-methoxysalicylaldehyde and crystallizes with two inde...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793792/ https://www.ncbi.nlm.nih.gov/pubmed/24109379 http://dx.doi.org/10.1107/S1600536813019727 |
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author | Sethuram, M. Bhargavi, G. Dhandapani, M. Amirthaganesan, G. NizamMohideen, M. |
author_facet | Sethuram, M. Bhargavi, G. Dhandapani, M. Amirthaganesan, G. NizamMohideen, M. |
author_sort | Sethuram, M. |
collection | PubMed |
description | The title compound, C(14)H(20)N(4)O(4)·0.5H(2)O [systematic name: (2S)-5-{[amino(iminiumyl)methyl]amino}-2-{[(1Z)-4-methoxy-2-oxidobenzylidene]azaniumyl}pentanoate hemihydrate], has been synthesized by the reaction of l-arginine and 4-methoxysalicylaldehyde and crystallizes with two independent substituted l-arginine molecules and one water molecule of solvation in the asymmetric unit. Each molecule exists as a zwitterion and adopts a Z configuration about the central C=N. The molecular conformation is stabilized by strong intramolecular N—H⋯O hydrogen bonds that generate S(6) and S(10) ring motifs. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds involving also the water molecule and weak intermolecular C—H⋯O(water) interactions link the molecules into an infinite one-dimensional ribbon structure extending along the b axis. The known (2S) absolute configuration for l-arginine was invoked. Weak intermolecular C—H⋯π interactions are also present. |
format | Online Article Text |
id | pubmed-3793792 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-37937922013-10-09 N (2)-(4-Methoxysalicylidene)arginine hemihydrate Sethuram, M. Bhargavi, G. Dhandapani, M. Amirthaganesan, G. NizamMohideen, M. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(14)H(20)N(4)O(4)·0.5H(2)O [systematic name: (2S)-5-{[amino(iminiumyl)methyl]amino}-2-{[(1Z)-4-methoxy-2-oxidobenzylidene]azaniumyl}pentanoate hemihydrate], has been synthesized by the reaction of l-arginine and 4-methoxysalicylaldehyde and crystallizes with two independent substituted l-arginine molecules and one water molecule of solvation in the asymmetric unit. Each molecule exists as a zwitterion and adopts a Z configuration about the central C=N. The molecular conformation is stabilized by strong intramolecular N—H⋯O hydrogen bonds that generate S(6) and S(10) ring motifs. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds involving also the water molecule and weak intermolecular C—H⋯O(water) interactions link the molecules into an infinite one-dimensional ribbon structure extending along the b axis. The known (2S) absolute configuration for l-arginine was invoked. Weak intermolecular C—H⋯π interactions are also present. International Union of Crystallography 2013-07-24 /pmc/articles/PMC3793792/ /pubmed/24109379 http://dx.doi.org/10.1107/S1600536813019727 Text en © Sethuram et al. 2013 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 Sethuram, M. Bhargavi, G. Dhandapani, M. Amirthaganesan, G. NizamMohideen, M. N (2)-(4-Methoxysalicylidene)arginine hemihydrate |
title |
N
(2)-(4-Methoxysalicylidene)arginine hemihydrate |
title_full |
N
(2)-(4-Methoxysalicylidene)arginine hemihydrate |
title_fullStr |
N
(2)-(4-Methoxysalicylidene)arginine hemihydrate |
title_full_unstemmed |
N
(2)-(4-Methoxysalicylidene)arginine hemihydrate |
title_short |
N
(2)-(4-Methoxysalicylidene)arginine hemihydrate |
title_sort | n
(2)-(4-methoxysalicylidene)arginine hemihydrate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793792/ https://www.ncbi.nlm.nih.gov/pubmed/24109379 http://dx.doi.org/10.1107/S1600536813019727 |
work_keys_str_mv | AT sethuramm n24methoxysalicylideneargininehemihydrate AT bhargavig n24methoxysalicylideneargininehemihydrate AT dhandapanim n24methoxysalicylideneargininehemihydrate AT amirthaganesang n24methoxysalicylideneargininehemihydrate AT nizammohideenm n24methoxysalicylideneargininehemihydrate |