1,2-Diphenyl-2-(phenyldiazenyl)-2-tosylethanone, an example of a fungicide containing a sulfonyl group.
The molecule of the title compound, C(27)H(22)N(2)O(3)S, adopts an irregular propeller shape with the tetrahedral C1 atom pivotal. The alpha-azophenyl and alpha-phenyl moieties are approximately coplanar. Electrostatic attraction of the oppositely charged atoms generates several short intramolecular contacts involving the sulfonyl, azo and carbonyl groups. Characteristic bond-length distribution of the central part of the molecule indicates that the Coulombic charge transfer is supplemented by hyperconjugation involving donation of electron density from the azo moiety towards the sulfonyl and 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
D001391:Azo Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005659:Fungicides, Industrial / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D014105:Tosyl Compounds / Q000737:chemistry*
C420699:1,2-diphenyl-2-(phenyldiazenyl)-2-tosylethanone; D001391:Azo Compounds; D005659:Fungicides, Industrial; D014105:Tosyl Compounds