Nobukazu Okazaki, A. Okumura
Jul 1, 1961
Citations
0
Influential Citations
4
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The rearrangement of N-deuterated aromatic amine hydrochloride into its ring-deuterated analogues has been studied in the solid and the liquid phases with o- and m-toluidines, and studied kinetically with anilinium chloride and bromide at 173∼194°C and at 210∼225°C, respectively. The ease of the rearrangement of the hydrochlorides in the solid phase is in the order, o-toluidine hydrochloride >aniline hydrochloride >p-toluidine hydrochloride which is the reverse of the order of the basic dissociation constants of the amines at 25°C. m-Toluidine hydrochloride is more reactive than o-toluidine hydrochloride. The numbers of nuclear hydrogen atoms which take part in the rearrangement are, 2 in the solid phase and >3 in the liquid phase rearrangement of o-toluidine hydrochloride, and for m-toluidine hydrochloride 3 and 4 in the solid and the liquid phases respectively. This result, taken in conjunction with the earlier ones with aniline and p-toluidine hydrochlorides, confirms the view that in the solid phase r...