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(S)-(+)-N-Benzyl­idene-1-(1-naphth­yl)ethyl­amine

In the title chiral aldimine, C(19)H(17)N, the azomethine group is not fully conjugated with the phenyl substituent: the dihedral angle between phenyl and C(*)—N=C mean planes is ϕ(3) = 23.0 (2)°. Compared with the earlier DFT-B3LYP/6–31 G(d) computations from the literature, the C=N—C(*)—C(naph­thy...

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Autores principales: Bernès, Sylvain, Hernández, Guadalupe, Vázquez, Jaime, Tovar, Alejandra, Gutiérrez, René
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089063/
https://www.ncbi.nlm.nih.gov/pubmed/21754547
http://dx.doi.org/10.1107/S1600536811012980
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author Bernès, Sylvain
Hernández, Guadalupe
Vázquez, Jaime
Tovar, Alejandra
Gutiérrez, René
author_facet Bernès, Sylvain
Hernández, Guadalupe
Vázquez, Jaime
Tovar, Alejandra
Gutiérrez, René
author_sort Bernès, Sylvain
collection PubMed
description In the title chiral aldimine, C(19)H(17)N, the azomethine group is not fully conjugated with the phenyl substituent: the dihedral angle between phenyl and C(*)—N=C mean planes is ϕ(3) = 23.0 (2)°. Compared with the earlier DFT-B3LYP/6–31 G(d) computations from the literature, the C=N—C(*)—C(naph­thyl) torsion angle, found at ϕ(2) = −118.0 (2)° in the X-ray structure, does not match the angle calculated for the potential minimum energy at ϕ(2) = 0°. However, this angle is close to the second potential energy minimum at ϕ(2) = −120° which is ca. 8.5 kJ mol(−1) above the global energy minimum. Thus, the reported X-ray structure corresponds to the second most likely (according to DFT) conformer, allowing the existence of other polymorphs to be anti­cipated.
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spelling pubmed-30890632011-07-13 (S)-(+)-N-Benzyl­idene-1-(1-naphth­yl)ethyl­amine Bernès, Sylvain Hernández, Guadalupe Vázquez, Jaime Tovar, Alejandra Gutiérrez, René Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title chiral aldimine, C(19)H(17)N, the azomethine group is not fully conjugated with the phenyl substituent: the dihedral angle between phenyl and C(*)—N=C mean planes is ϕ(3) = 23.0 (2)°. Compared with the earlier DFT-B3LYP/6–31 G(d) computations from the literature, the C=N—C(*)—C(naph­thyl) torsion angle, found at ϕ(2) = −118.0 (2)° in the X-ray structure, does not match the angle calculated for the potential minimum energy at ϕ(2) = 0°. However, this angle is close to the second potential energy minimum at ϕ(2) = −120° which is ca. 8.5 kJ mol(−1) above the global energy minimum. Thus, the reported X-ray structure corresponds to the second most likely (according to DFT) conformer, allowing the existence of other polymorphs to be anti­cipated. International Union of Crystallography 2011-04-29 /pmc/articles/PMC3089063/ /pubmed/21754547 http://dx.doi.org/10.1107/S1600536811012980 Text en © Bernès 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
Bernès, Sylvain
Hernández, Guadalupe
Vázquez, Jaime
Tovar, Alejandra
Gutiérrez, René
(S)-(+)-N-Benzyl­idene-1-(1-naphth­yl)ethyl­amine
title (S)-(+)-N-Benzyl­idene-1-(1-naphth­yl)ethyl­amine
title_full (S)-(+)-N-Benzyl­idene-1-(1-naphth­yl)ethyl­amine
title_fullStr (S)-(+)-N-Benzyl­idene-1-(1-naphth­yl)ethyl­amine
title_full_unstemmed (S)-(+)-N-Benzyl­idene-1-(1-naphth­yl)ethyl­amine
title_short (S)-(+)-N-Benzyl­idene-1-(1-naphth­yl)ethyl­amine
title_sort (s)-(+)-n-benzyl­idene-1-(1-naphth­yl)ethyl­amine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089063/
https://www.ncbi.nlm.nih.gov/pubmed/21754547
http://dx.doi.org/10.1107/S1600536811012980
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