(S)-(+)-N-Benzylidene-1-(1-naphthyl)ethylamine
In the title chiral aldimine, C19H17N, the azomethine group is not fully conjugated with the phenyl substituent: the dihedral angle between phenyl and C*—N=C mean planes is ϕ3 = 23.0 (2)°. Compared with the earlier DFT-B3LYP/6–31 G(d) computations from the literature, the C=N—C*—C(naphthyl) torsion...
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| Format: | Online |
| Language: | English |
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International Union of Crystallography
2011
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| Online Access: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089063/ |
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pubmed-3089063 |
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oai_dc |
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pubmed-30890632011-07-13 (S)-(+)-N-Benzylidene-1-(1-naphthyl)ethylamine Bernès, Sylvain Hernández, Guadalupe Vázquez, Jaime Tovar, Alejandra Gutiérrez, René Organic Papers In the title chiral aldimine, C19H17N, the azomethine group is not fully conjugated with the phenyl substituent: the dihedral angle between phenyl and C*—N=C mean planes is ϕ3 = 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 ϕ2 = −118.0 (2)° in the X-ray structure, does not match the angle calculated for the potential minimum energy at ϕ2 = 0°. However, this angle is close to the second potential energy minimum at ϕ2 = −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. |
| repository_type |
Open Access Journal |
| institution_category |
Foreign Institution |
| institution |
US National Center for Biotechnology Information |
| building |
NCBI PubMed |
| collection |
Online Access |
| language |
English |
| format |
Online |
| author |
Bernès, Sylvain Hernández, Guadalupe Vázquez, Jaime Tovar, Alejandra Gutiérrez, René |
| spellingShingle |
Bernès, Sylvain Hernández, Guadalupe Vázquez, Jaime Tovar, Alejandra Gutiérrez, René (S)-(+)-N-Benzylidene-1-(1-naphthyl)ethylamine |
| author_facet |
Bernès, Sylvain Hernández, Guadalupe Vázquez, Jaime Tovar, Alejandra Gutiérrez, René |
| author_sort |
Bernès, Sylvain |
| title |
(S)-(+)-N-Benzylidene-1-(1-naphthyl)ethylamine |
| title_short |
(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_sort |
(s)-(+)-n-benzylidene-1-(1-naphthyl)ethylamine |
| description |
In the title chiral aldimine, C19H17N, the azomethine group is not fully conjugated with the phenyl substituent: the dihedral angle between phenyl and C*—N=C mean planes is ϕ3 = 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 ϕ2 = −118.0 (2)° in the X-ray structure, does not match the angle calculated for the potential minimum energy at ϕ2 = 0°. However, this angle is close to the second potential energy minimum at ϕ2 = −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. |
| publisher |
International Union of Crystallography |
| publishDate |
2011 |
| url |
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089063/ |
| _version_ |
1611452246046801920 |