Abstract
Substituent effects on decomposition products of phenyl-substituted 1-furoyl-3-phenylthioureas were investigated, using a mass spectrometer with an indirect sample inlet system. It was demonstrated by means of correlational analysis, using Hammett σ constants, that the product formation (mainly furoyl isothiocyanate, aniline, furamide and phenyl isothiocyanate) is not influenced exclusively by the experimental conditions (pressure, temperature) but by an intrinsic factor such as the substituent in the molecule. A good correlation is observed between the ratio of furamide and furoyl isothiocyanate intensities compared with the non-substituted compound. The intercept is close to zero and the slope ( b = 0.305) shows that the electron-withdrawing substituents favor the proton migration of the most adjacent NH group to the benzene ring, very probably through a four-member cyclic transition-state mechanism.
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