Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10284/8172 |
Resumo: | The crystal structures of three benzamide derivatives, viz. N-(6-hy-droxy-hex-yl)-3,4,5-tri-meth-oxy-benzamide, C16H25NO5, (1), N-(6-anilinohex-yl)-3,4,5-tri-meth-oxy-benzamide, C22H30N2O4, (2), and N-(6,6-di-eth-oxy-hex-yl)-3,4,5-tri-meth-oxy-benzamide, C20H33NO6, (3), are described. These compounds differ only in the substituent at the end of the hexyl chain and the nature of these substituents determines the differences in hydrogen bonding between the mol-ecules. In each mol-ecule, the m-meth-oxy substituents are virtually coplanar with the benzyl ring, while the p-meth-oxy substituent is almost perpendicular. The carbonyl O atom of the amide rotamer is trans related with the amidic H atom. In each structure, the benzamide N-H donor group and O acceptor atoms link the mol-ecules into C(4) chains. In 1, a terminal -OH group links the mol-ecules into a C(3) chain and the combined effect of the C(4) and C(3) chains is a ribbon made up of screw related R 2 (2)(17) rings in which the ⋯O-H⋯ chain lies in the centre of the ribbon and the tri-meth-oxy-benzyl groups forms the edges. In 2, the combination of the benzamide C(4) chain and the hydrogen bond formed by the terminal N-H group to an O atom of the 4-meth-oxy group link the mol-ecules into a chain of R 2 (2)(17) rings. In 3, the mol-ecules are linked only by C(4) chains. |
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Crystal structures of three 3,4,5-trimethoxybenzamide-based derivativesBenzamideCrystal structureHydrogen bondingThe crystal structures of three benzamide derivatives, viz. N-(6-hy-droxy-hex-yl)-3,4,5-tri-meth-oxy-benzamide, C16H25NO5, (1), N-(6-anilinohex-yl)-3,4,5-tri-meth-oxy-benzamide, C22H30N2O4, (2), and N-(6,6-di-eth-oxy-hex-yl)-3,4,5-tri-meth-oxy-benzamide, C20H33NO6, (3), are described. These compounds differ only in the substituent at the end of the hexyl chain and the nature of these substituents determines the differences in hydrogen bonding between the mol-ecules. In each mol-ecule, the m-meth-oxy substituents are virtually coplanar with the benzyl ring, while the p-meth-oxy substituent is almost perpendicular. The carbonyl O atom of the amide rotamer is trans related with the amidic H atom. In each structure, the benzamide N-H donor group and O acceptor atoms link the mol-ecules into C(4) chains. In 1, a terminal -OH group links the mol-ecules into a C(3) chain and the combined effect of the C(4) and C(3) chains is a ribbon made up of screw related R 2 (2)(17) rings in which the ⋯O-H⋯ chain lies in the centre of the ribbon and the tri-meth-oxy-benzyl groups forms the edges. In 2, the combination of the benzamide C(4) chain and the hydrogen bond formed by the terminal N-H group to an O atom of the 4-meth-oxy group link the mol-ecules into a chain of R 2 (2)(17) rings. In 3, the mol-ecules are linked only by C(4) chains.International Union of CrystallographyRepositório Institucional da Universidade Fernando PessoaGomes, Ligia R.Low, John NicolsonOliveira, CatarinaCagide, FernandoBorges, Fernanda2019-10-24T18:32:38Z2016-01-01T00:00:00Z2016-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10284/8172engGomes, L. R., Low, J. N., Oliveira, C., Cagide, F., & Borges, F. (2016). Crystal structures of three 3,4,5-tri-meth-oxy-benzamide-based derivatives. Acta crystallographica. Section E, Crystallographic communications, 72(Pt 5), 675–682. doi:10.1107/S20569890160059582056-989010.1107/S2056989016005958info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2022-09-06T02:07:33Zoai:bdigital.ufp.pt:10284/8172Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T15:45:03.660084Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives |
title |
Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives |
spellingShingle |
Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives Gomes, Ligia R. Benzamide Crystal structure Hydrogen bonding |
title_short |
Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives |
title_full |
Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives |
title_fullStr |
Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives |
title_full_unstemmed |
Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives |
title_sort |
Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives |
author |
Gomes, Ligia R. |
author_facet |
Gomes, Ligia R. Low, John Nicolson Oliveira, Catarina Cagide, Fernando Borges, Fernanda |
author_role |
author |
author2 |
Low, John Nicolson Oliveira, Catarina Cagide, Fernando Borges, Fernanda |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Repositório Institucional da Universidade Fernando Pessoa |
dc.contributor.author.fl_str_mv |
Gomes, Ligia R. Low, John Nicolson Oliveira, Catarina Cagide, Fernando Borges, Fernanda |
dc.subject.por.fl_str_mv |
Benzamide Crystal structure Hydrogen bonding |
topic |
Benzamide Crystal structure Hydrogen bonding |
description |
The crystal structures of three benzamide derivatives, viz. N-(6-hy-droxy-hex-yl)-3,4,5-tri-meth-oxy-benzamide, C16H25NO5, (1), N-(6-anilinohex-yl)-3,4,5-tri-meth-oxy-benzamide, C22H30N2O4, (2), and N-(6,6-di-eth-oxy-hex-yl)-3,4,5-tri-meth-oxy-benzamide, C20H33NO6, (3), are described. These compounds differ only in the substituent at the end of the hexyl chain and the nature of these substituents determines the differences in hydrogen bonding between the mol-ecules. In each mol-ecule, the m-meth-oxy substituents are virtually coplanar with the benzyl ring, while the p-meth-oxy substituent is almost perpendicular. The carbonyl O atom of the amide rotamer is trans related with the amidic H atom. In each structure, the benzamide N-H donor group and O acceptor atoms link the mol-ecules into C(4) chains. In 1, a terminal -OH group links the mol-ecules into a C(3) chain and the combined effect of the C(4) and C(3) chains is a ribbon made up of screw related R 2 (2)(17) rings in which the ⋯O-H⋯ chain lies in the centre of the ribbon and the tri-meth-oxy-benzyl groups forms the edges. In 2, the combination of the benzamide C(4) chain and the hydrogen bond formed by the terminal N-H group to an O atom of the 4-meth-oxy group link the mol-ecules into a chain of R 2 (2)(17) rings. In 3, the mol-ecules are linked only by C(4) chains. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-01-01T00:00:00Z 2016-01-01T00:00:00Z 2019-10-24T18:32:38Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10284/8172 |
url |
http://hdl.handle.net/10284/8172 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Gomes, L. R., Low, J. N., Oliveira, C., Cagide, F., & Borges, F. (2016). Crystal structures of three 3,4,5-tri-meth-oxy-benzamide-based derivatives. Acta crystallographica. Section E, Crystallographic communications, 72(Pt 5), 675–682. doi:10.1107/S2056989016005958 2056-9890 10.1107/S2056989016005958 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
International Union of Crystallography |
publisher.none.fl_str_mv |
International Union of Crystallography |
dc.source.none.fl_str_mv |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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