Two conformational diastereoisomers due to the hindered Aryl-NSO2 rotation were observed by NMR in the model compound N,N’-bis-tosyl-N,N’-dipropargyl-1,4-diamine-2,3-dimethyl benzene 1. X-Ray analysis showed that only the syn conformation is present in the solid state. The conformational preference in solution was evaluated by DFT calculations and experimentally determined by low-temperature NMR experiments. It was found that the anti conformation is the more populated in low-polarity solvents whereas the syn is the favored one in polar solvents.
Stefano Menichetti, Chiara Biagioli, Caterina Viglianisi, Lorenzo Tofani, Lodovico Lunazzi, Michele Mancinelli, et al. (2015). Structure and conformational dynamics of an aromatic sulfonamide: NMR, X-Ray and computational studies. ARKIVOC, 2015(4), 66-79 [10.3998/ark.5550190.p008.974].
Structure and conformational dynamics of an aromatic sulfonamide: NMR, X-Ray and computational studies
MANCINELLI, MICHELE;MAZZANTI, ANDREA
2015
Abstract
Two conformational diastereoisomers due to the hindered Aryl-NSO2 rotation were observed by NMR in the model compound N,N’-bis-tosyl-N,N’-dipropargyl-1,4-diamine-2,3-dimethyl benzene 1. X-Ray analysis showed that only the syn conformation is present in the solid state. The conformational preference in solution was evaluated by DFT calculations and experimentally determined by low-temperature NMR experiments. It was found that the anti conformation is the more populated in low-polarity solvents whereas the syn is the favored one in polar solvents.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
