Mukaiyama, Teruaki published the artcileThe effects of substituents on the hydrolysis of substituted cyanamides in sulfuric acid solution, Category: amides-buliding-blocks, the publication is Bulletin of the Chemical Society of Japan (1954), 416-21, database is CAplus.
The following RR’NCN were prepared either from RR’NH and BrCN, or (where R and R’ are the same) from the corresponding halide and Na2NCN [R, R’, b.p. (mm.) given, resp.]: Et, H, 94-5° (4); Bu, H, 117° (14); n-heptyl, H, nondistillable; iso-Pr, H, 108° (10); tert-Bu, H, 109-10° (11); allyl, H, 92° (3); Ph, H, -, m. 42°; Et, Et, 78° (16); Bu, Bu, 120-1° (16); iso-Pr, iso-Pr, 93-4° (25); allyl, allyl, 107-8° (18); PhCH2, PhCH2, m. 53.5°. The hydrolysis of 0.1M solutions of the RR’NCN in 3:1 dioxane-water containing 20% by weight of H2SO4 was followed kinetically by contraction in volume, measured with a dilatometer. All of the ureas thus produced were known compounds except N,N-diallylurea, m. 64° (from petr. ether). Tables of rate constants at different temperatures, activation energies, and entropies of activation are given for hydrolysis of the various cyanamides. The rate of reaction increases in the series: (iso-Pr)2, Et2, Ph, tert.-Bu, H2, iso-Pr, Et, heptyl. From these results it is proposed that the rate-determining step in the hydrolysis mechanism is the protonation of the cyanamide bisulfate, RR’NC(:NH)OSO3H, which is in turn dependent upon the basic strength of the cyanamide. This hypothesis is not in accord with the mechanism proposed by Kilpatrick (C.A. 41, 1916g).
Bulletin of the Chemical Society of Japan published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Category: amides-buliding-blocks.
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https://en.wikipedia.org/wiki/Amide,
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