Cargando…

2-[(Naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol

The title compound, C(18)H(15)NO, is a Schiff base prepared from an acid-catalyzed condensation reaction between 1-naphthaldehyde and 6-amino-m-cresol. Intra­molecular hydrogen bonding occurs via an O—H⋯N inter­action, generating an S(5) ring motif. Neighboring phenol groups participate in inter­mol...

Descripción completa

Detalles Bibliográficos
Autores principales: Orona, Gabriella, Molinar, Vanessa, Fronczek, Frank R., Isovitsch, Ralph
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200862/
https://www.ncbi.nlm.nih.gov/pubmed/22059051
http://dx.doi.org/10.1107/S1600536811034556
_version_ 1782214766346895360
author Orona, Gabriella
Molinar, Vanessa
Fronczek, Frank R.
Isovitsch, Ralph
author_facet Orona, Gabriella
Molinar, Vanessa
Fronczek, Frank R.
Isovitsch, Ralph
author_sort Orona, Gabriella
collection PubMed
description The title compound, C(18)H(15)NO, is a Schiff base prepared from an acid-catalyzed condensation reaction between 1-naphthaldehyde and 6-amino-m-cresol. Intra­molecular hydrogen bonding occurs via an O—H⋯N inter­action, generating an S(5) ring motif. Neighboring phenol groups participate in inter­molecular hydrogen bonding through an O—H⋯O inter­action, forming chains. The O atom of the phenol group also participates in an intermolecular C—H⋯O interaction with an H atom of one of the naphthalene rings. The C—N=C—C torsion angle between the phenol and naphthalene rings is −179.8 (2)°. Crystal packing involves stacks with the mol­ecules inter­acting through the π-systems of the C=N with both the phenol system and one of the naphthalene rings.
format Online
Article
Text
id pubmed-3200862
institution National Center for Biotechnology Information
language English
publishDate 2011
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-32008622011-11-06 2-[(Naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol Orona, Gabriella Molinar, Vanessa Fronczek, Frank R. Isovitsch, Ralph Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(15)NO, is a Schiff base prepared from an acid-catalyzed condensation reaction between 1-naphthaldehyde and 6-amino-m-cresol. Intra­molecular hydrogen bonding occurs via an O—H⋯N inter­action, generating an S(5) ring motif. Neighboring phenol groups participate in inter­molecular hydrogen bonding through an O—H⋯O inter­action, forming chains. The O atom of the phenol group also participates in an intermolecular C—H⋯O interaction with an H atom of one of the naphthalene rings. The C—N=C—C torsion angle between the phenol and naphthalene rings is −179.8 (2)°. Crystal packing involves stacks with the mol­ecules inter­acting through the π-systems of the C=N with both the phenol system and one of the naphthalene rings. International Union of Crystallography 2011-08-27 /pmc/articles/PMC3200862/ /pubmed/22059051 http://dx.doi.org/10.1107/S1600536811034556 Text en © Orona et al. 2011 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
Orona, Gabriella
Molinar, Vanessa
Fronczek, Frank R.
Isovitsch, Ralph
2-[(Naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol
title 2-[(Naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol
title_full 2-[(Naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol
title_fullStr 2-[(Naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol
title_full_unstemmed 2-[(Naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol
title_short 2-[(Naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol
title_sort 2-[(naphthalen-1-yl­methyl­idene)amino]-5-methyl­phenol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200862/
https://www.ncbi.nlm.nih.gov/pubmed/22059051
http://dx.doi.org/10.1107/S1600536811034556
work_keys_str_mv AT oronagabriella 2naphthalen1ylmethylideneamino5methylphenol
AT molinarvanessa 2naphthalen1ylmethylideneamino5methylphenol
AT fronczekfrankr 2naphthalen1ylmethylideneamino5methylphenol
AT isovitschralph 2naphthalen1ylmethylideneamino5methylphenol