A three-dimensional analysis of a second compound containing the group C---C=:N--R is described.Crystals of N-methyl-2-methylsulphonyl-2-phenylsulphonylvinylidineamine are monoclinic P2~/a with a = 15.248,b ----13.030,c = 10.660/~ and fl -~ 144 ° 27'.The results confirm that the vinylidineamine group is linear, and the abnormal bond lengths are corroborated.An attempt is made to account qualitatively for the linearity of this group, and it is suggested that two factors are operative.The presence of electronegative groups on the methylene carbon atom, which are essential for the stability of vinylidineamines, will tend to straighten the chain, and hyperconjugation between the group R and the multiply-linked chain will have the same effect.It is possible that the relative importance of these two factors may be investigated experimentally by changing R.
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Bullough et al. (1957) studied this question.