1 research outputs found
Application of the Systems Chemistry Approach on the Ammonolysis of 1âEthoxycarbonyl- and 1âPhenoxycarbonyl-3-(2-thienyl)oxindoles. A Method to Predict Reactivity
The routine prediction of the reactivity of a complex,
multifunctional
molecule is a challenging and time-consuming procedure. In the last
step of the synthesis of the well-known drug substance tenidap, a
nonexpected difference was observed between the reactivities of two
closely related carbamate moieties, the <i>N</i>-ethoxycarbonyl
and the <i>N</i>-phenoxycarbonyl group. A detailed kinetic
study, necessitating a significant computational effort, is described
in the present paper for this reaction step. On the other hand, the
systems chemistry concept, by analyzing the details of the electronic
structure and the connections between functional groups in a fast
and simple way, is also able to answer this question using various
â-icityâ parameters (aromaticity, carbonylicity, olefinicity).
The complete systems chemistry approach involves all these conjugativicity
parameters, while its further simplified version is based on only
one key parameter, which is carbonylicity in the present case. The
above methods were compared in terms of their predictive power. The
results show that the systems chemistry concept, even its one-parameter
version, is applicable for the characterization of this challenging
reactivity issue