X-ray investigations of sulfur-containing fungicides. IV. 4'-[[Benzoyl(4-chlorophenylhydrazono)methyl]sulfonyl]acetanilide and 4'-[[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl]acetanilide.
The conformations of the two approximately isomorphous structures 4'-[[benzoyl(4-chlorophenylhydrazono)methyl]sulfonyl]acetanilide, C(22)H(18)ClN(3)O(4)S, and 4'-[[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl]acetanilide, C(23)H(21)N(3)O(5)S, are stabilized by resonance-assisted intramolecular hydrogen bonds linking the hydrazone moieties and sulfonyl groups. The stronger bond is observed in the former compound. The difference in electronic properties between the Cl atom and the methoxy group is too small to significantly alter the non-bonding interactions of the sulfonyl and beta-carbonyl groups.
Wolf
W M
WM
Institute of General and Ecological Chemistry, Technical University of Lódz, ul. Zwirki 36, 90-924 Lódz, Poland. wmwolf@p.lodz.pl
D000083:Acetanilides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005659:Fungicides, Industrial / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D015394:Molecular Structure; D055672:Static Electricity; D013450:Sulfones / Q000737:chemistry*
C438264:4'-((benzoyl(4-chlorophenylhydrazono)methyl)sulfonyl)acetanilide; C438263:4'-((benzoyl(4-methoxyphenylhydrazono)methyl)sulfonyl)acetanilide; D000083:Acetanilides; D005659:Fungicides, Industrial; D006835:Hydrazones; D013450:Sulfones