Tricyanomethyl moiety

A series of tricyanomethyl compounds were prepared in refluxing acetonitrile hy alkylating potassium tricyanometha-nide with alkyl iodides, allyl, propargyl, and benzyl bromides. Yields of 20-57% were obtained for mono- and difunctional halides with a reflux time of 72 hours. The heats of combustion of these tricyanomethyl compounds as well as of two polycyano compounds were measured using a Dickenson-type calorimeter, and heats of formation were calculated with a precision of approximately 1.0%. From Pitzers values for C—C and C—H bond energies, that of the tricyanomethyl moiety is calculated to be about 810 kcal./mole, and the tricyanomethyl group is less stable than expected from comparison with AH°f of propylcyanide. 

It is also possible to calculate the bond energy of the tricyanomethyl moiety in each of the molecules. To do this we calculate standard heats of formation at 0° K. from the values given in Table III for 298° C. In the absence of reliable data we note the following reported (13) specific heats, Cp ... 

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See also in sourсe #XX -- [ ]

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