Substituted ammonium salts of benzothiazoline-2-thione. Nuclear magnetic resonance studies of ion pairs in polar and nonpolar media

1973 ◽  
Vol 38 (7) ◽  
pp. 1353-1355 ◽  
Author(s):  
Adel F. Halasa ◽  
G. E. P. Smith

N. m. r. studies of 9, 10-dihydroanthracene, its 10-alkyl substituted derivatives and of the respective Li + salts established the stereochemistry of these compounds. The spectra show that neither the molecules of these hydrocarbons nor of their lithium salts are planar, although in the anions the carbon 9 atoms possess a considerable amount of sp 2 character. The anion of the unsubstituted salt vibrates rapidly through the planar configuration while the substituted anion prefers one conformation, apparently that in which the alkyl group is equatorial. The n. m. r. spectrum of the unsubstituted salt is compared with those of the lithium salts of some similar hydrocarbons, namely, fluorene and diphenylmethane.


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