Bioactive four-membered heterocyclic compounds: the anti --> syn interconversion in dithietane-1,3-dioxide.
The anti-dithietane-1,3-dioxide --> syn-dithietane-1,3-dioxide isomerization reaction has been theoretically studied on the frame of MO theory both in the gas phase and in solution. In the gas phase the anti (II(a)) <--> syn (II(s)) equilibrium is slightly displaced to the anti isomer formation. The syn concentration ([Syn]) is ca. 36% in the gas phase, whereas in low polarity solvent, such as carbon tetrachloride, [Syn] is ca. 63%. In medium-high polarity solvents like acetonitrile and dimethyl-sulfoxide the [ anti]/[ syn ] ratio is ca. 0.37.
Contreras
J G
JG
Grupo de Quimica Teorica y Computacional, Universidad de Concepcion, Concepcion, Casilla 160-C, Chile. gcontrer@udec.cl
Madariaga
S T
ST
D000097:Acetonitriles; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D012997:Solvents; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
D000097:Acetonitriles; D006571:Heterocyclic Compounds; D012997:Solvents; D013440:Sulfides; C445704:dithietane-1,3-dioxide; D004121:Dimethyl Sulfoxide