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Communication | Special issue | Vol 18, No. 1, 1982, pp.51-56
Published online, 1st January, 1970
DOI: 10.3987/S(B)-1982-01-0051
Solvent Effects in Conformational Equilibria of Onium Salts

Kwang-Ting Liu, Ernest L. Eliel,* and William Rand Kenan Jr.

*Laboratories of Chemistry, University of North Carolina, Chapel Hill, NC 27599-3290, U.S.A.


The equilibria of the S-methyl group in cis- and trans-S-methyl-4-t-butylthianium salts and of the N-methyl groups in corresponding N-methyl-4-t-butylpiperidinium and N-cis-2,6-trimethylpiperidinium salts have been studied as a function of solvent, concentration and gegenion. The effects of these factors are appreciable, causing variations of up to 0.2 kcal/mol in ΔG° in the thianium and 0.4 kcal/mol in the piperidinium salts. Rationalizations for these effects are provided.