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Zwitterionic (E)-1-[(4-nitro-phen-yl)iminio-meth-yl]naphthalen-2-olate.

ABSTRACT: The title compound, C(17)H(12)N(2)O(3), was synthesized by the reaction of 2-hy-droxy-1-naphthaldehyde with 4-nitro-benzenamine. These condense to form the Schiff base, which crystallizes in the zwitterionic form. In the structure, the keto-amino tautomer has a fairly short intra-molecular N-H?O hydrogen bond between the 2-naphthalenone and amino groups, with electron delocalization. The mol-ecule is essentially planar, with a dihedral angle of 1.96?(3)° between the ring systems. In the crystal, the mol-ecules are linked via inter-molecular C-H?O hydrogen bonds, forming a layer parallel to (101).

SUBMITTER: Damous M

PROVIDER: S-EPMC3089354 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Zwitterionic (E)-1-[(4-nitro-phen-yl)iminio-meth-yl]naphthalen-2-olate.

Damous Maamar M Hamlaoui Meriem M Bouacida Sofiane S Merazig Hocine H Daran Jean-Claude JC

Acta crystallographica. Section E, Structure reports online 20110413 Pt 5

The title compound, C(17)H(12)N(2)O(3), was synthesized by the reaction of 2-hy-droxy-1-naphthaldehyde with 4-nitro-benzenamine. These condense to form the Schiff base, which crystallizes in the zwitterionic form. In the structure, the keto-amino tautomer has a fairly short intra-molecular N-H⋯O hydrogen bond between the 2-naphthalenone and amino groups, with electron delocalization. The mol-ecule is essentially planar, with a dihedral angle of 1.96 (3)° between the ring systems. In the crystal, ...[more]

PMID: 21754437

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