Journal of the Chemical Society. Perkin transactions II p. 1881 - 1886 (1993)
Update date:2022-08-04
Topics:
Dahn, Hans
Pechy, Peter
Toan, Vien Van
Bonini, Bianca F.
Lunazzi, Lodovico
et al.
The 17O NMR shift values δo of 20 sulfinylamines R-N=S=O 2 and of 14 sulfines RR'C=S=O 3 (R and R' mostly arene groups) were compared with those of the isoelectronic SO2 1.They show δo at much lower field than practically all other classes of S-O compounds; at the same time they exhibit the high substituent sensitivity which is typical for true ?p bond systems, and absent in S+-O- compounds.The difference is discussed in terms of bond order and electronic excitation energy.Comparison of the E- and Z isomers of o-methyldiaryl sulfines yields the conformation of these compounds: one arene ring is (nearly) complanar with the CSO group and the other (nearly) perpendicular to it.This demonstration for the molecules in solution is supported by an X-ray structure determination.
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