Literature DB >> 21200729

3-[(Z)-(4-Diethyl-amino-6-oxocyclo-hexa-2,4-dien-1-yl-idene)methyl-amino]benzoic acid.

M T Swamy, B Narayana, H S Yathirajan, B K Sarojini, Maciej Kubicki.   

Abstract

The title compound, C(18)H(20)N(2)O(3), crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydr-oxy tautomer. There are two strong n class="Chemical">hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intra-molecular N-H⋯O and one inter-molecular O-H⋯O. As a result, the carbonyl C=O distance is long, at 1.310 (2) Å, which may suggest the mol-ecule has a significant zwitterionic character. The dihedral angle between the benzene ring planes is 15.05 (7)°. As a result of the intramolecular hydrogen bond, the bridging C-C=N-C group is almost coplanar with the benzene ring that has the diethylamino substituent [dihedral angle 2.35 (15)°].

Entities:  

Year:  2007        PMID: 21200729      PMCID: PMC2915231          DOI: 10.1107/S1600536807064446

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


  2 in total

1.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

2.  Structure-antitumor activity correlation of some Schiff bases.

Authors:  E M Hodnett; W J Dunn
Journal:  J Med Chem       Date:  1970-07       Impact factor: 7.446

  2 in total

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