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Synthesis and Structural Assignment of Oxanilo‐ N ‐arylhydrazonoyl Chlorides
Author(s) -
Frohberg Petra,
Drutkowski Guntram,
Wagner Christoph
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200205)2002:10<1654::aid-ejoc1654>3.0.co;2-u
Subject(s) - chemistry , moiety , intramolecular force , hydrogen bond , amide , aryl , hydrazone , crystal structure , nuclear magnetic resonance spectroscopy , hydrogen atom , chloride , crystallography , medicinal chemistry , photochemistry , stereochemistry , molecule , organic chemistry , alkyl
Oxanilo‐ N ‐arylhydrazonoyl chlorides have been prepared from appropriate N ‐aryl‐2‐chloro‐3‐oxobutanamides by the Japp−Klingemann reaction. The structures of the title compounds have been established in the solid state by single‐crystal X‐ray structure determination and IR spectroscopy, and in solution by IR, UV, and 1 H and 13 C NMR spectroscopy. The results indicate that the hydrazonoyl chloride moiety adopts the ( Z )‐configured form. In the crystal, intramolecular hydrogen bonds generally exist between the chloride function and the hydrazone hydrogen atom, and also between the amide hydrogen atom and the double‐bonded nitrogen atom of the hydrazone moiety. In solution, this intramolecular hydrogen bonding could not be detected. In compounds with an ortho ‐chloro‐substituted NH−aryl moiety, however, the chlorine atom is involved in hydrogen bonding to the NH hydrogen atom both in the crystal and in solution. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)