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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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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 |
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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 |
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