6533b7cefe1ef96bd12570dd
RESEARCH PRODUCT
Rearrangement products of 3-methanesulfonyl-N-methyl-N-nitroaniline.
Zdzisław DaszkiewiczJanusz B. KyziołJacek ZaleskiBartosz Zarychtasubject
Steric effectsChemistryStereochemistryHydrogen bondMoleculeAromaticityGeneral MedicineCrystal structureSigmatropic reactionMedicinal chemistryGeneral Biochemistry Genetics and Molecular BiologyNitroanilineCope rearrangementdescription
Two isomeric products (C 8 H 10 N 2 O 4 S) of the rearrangement of 3-methanesulfonyl-N-methyl-N-nitroaniline have been investigated, viz. 3-methanesulfonyl-N-methyl-2-nitroaniline, which was the main product of the rearrangement, and 5-methanesulfonyl-N-methyl-2-nitroaniline. In both molecules, the aromatic rings are appreciably deformed towards ortho-quinonoidal geometry by electronic and steric interactions. The crystal structure is stabilized, in both cases, by weak C-H...O hydrogen bonds.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-07-10 | Acta crystallographica. Section C, Crystal structure communications |