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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...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2011
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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. |
format | Text |
id | pubmed-3089063 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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