Abstract
The effect of various Lewis acids on the optical rotatory power of nicotine has been studied in dimethylformamide or in toluene. The optical rotation of nicotine was increased by the action of most Lewis acids. The difference between the specific rotation of free nicotine and that of nicotine co-ordinated to a Lewis acid decreases along the sequence SbCl 5 > SnCl 4 > SbCl 3 > AlI 3 ⪆ FeCl 3 > AlBr 3 > AlCl 3 > TiCl 4 ⪢ ZnCl 2 ZnCl 2 ⪆ HgCl 2 ⪆ CdCl 2 among various metal halides, and AlEtCl 2 > AlEt 3 > AlEt 2Cl among organo-aluminum compounds. These orders seem to be correlated with the acidities of the Lewis acids, and show reasonable agreement with those obtained by other methods. The optical rotatory dispersion of the complex with SnCl 4 was examined, and the mechanism of the rotational change discussed in relation to the optical rotatory dispersion of nicotine hydrochloride.
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