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(S)-(+)-N-Benzyl-idene-1-(1-naphth-yl)ethyl-amine.

ABSTRACT: 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 ?(3) = 23.0?(2)°. Compared with the earlier DFT-B3LYP/6-31?G(d) computations from the literature, the C=N-C(*)-C(naph-thyl) torsion angle, found at ?(2) = -118.0?(2)° in the X-ray structure, does not match the angle calculated for the potential minimum energy at ?(2) = 0°. However, this angle is close to the second potential energy minimum at ?(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 anti-cipated.

SUBMITTER: Bernes S

PROVIDER: S-EPMC3089063 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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(S)-(+)-N-Benzyl-idene-1-(1-naphth-yl)ethyl-amine.

Bernès Sylvain S Hernández Guadalupe G Vázquez Jaime J Tovar Alejandra A Gutiérrez René R

Acta crystallographica. Section E, Structure reports online 20110429 Pt 5

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(naph-thyl) 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 pote ...[more]

PMID: 21754547

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