2005ARKIVOCOpen access

Structural correlations among aromatic azine derivatives

T. G. D. van Schalkwyk, Alistair M. Stephen

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Abstract

This paper is a sequel to the ARKIVOC publication [2002 (iii) 103-111] describing the spontaneous conversion of the methochloride (A) of salicylaldazine to the azine (B), which is considered to take place via the oxidation of an N-alkylhydrazone.X-Ray crystallographic aspects of (A), (B) and three related compounds are presented, and a survey given of the conformations of a number of derivatives of the parent compound benzaldazine.Three categories of structure are discerned, one essentially planar, another twisted as a consequence of steric interactions in the neighborhood of the azine system, and a third group having further distinctive features including extreme deviations from planarity.

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What this paper is about

This paper is a sequel to the ARKIVOC publication [2002 (iii) 103-111] describing the spontaneous conversion of the methochloride (A) of salicylaldazine to the azine (B), which is considered to take place via the oxidation of an N-alkylhydrazone.X-Ray crystallographic aspects of (A), (B) and three related compounds are presented, and a survey given of the conformations of a number of derivatives of the parent compound benzaldazine.Three categories of structure are discerned, one essentially planar, another twisted as a consequence of steric interactions in the neighborhood of the azine system, and a third group having further distinctive features including extreme deviations from planarity.

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Available abstract

This paper is a sequel to the ARKIVOC publication [2002 (iii) 103-111] describing the spontaneous conversion of the methochloride (A) of salicylaldazine to the azine (B), which is considered to take place via the oxidation of an N-alkylhydrazone.X-Ray crystallographic aspects of (A), (B) and three related compounds are presented, and a survey given of the conformations of a number of derivatives of the parent compound benzaldazine.Three categories of structure are discerned, one essentially planar, another twisted as a consequence of steric interactions in the neighborhood of the azine system, and a third group having further distinctive features including extreme deviations from planarity.

Key concepts: Azine, Planarity testing, Chemistry, Steric effects, Crystallography, Stereochemistry, Computational chemistry, Medicinal chemistry

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