Quantifying the enamine-type nucleophilic reactivity of α-aryl vinyl azides | Synapse
February 19, 2026Open Access
Quantifying the enamine-type nucleophilic reactivity of α-aryl vinyl azides
Key Points
This research aims to quantify the nucleophilicity of various vinyl azides and analyze their reactivity.
Determination of nucleophilicities for eight vinyl azides in CH2Cl2 and Cyrene.
Use of DFT calculations to derive H3C+ affinities for the azides.
Establishment of a linear correlation between nucleophilicity and calculated affinities.
Quantitative data shows nucleophilicities of the eight azides correlate linearly with DFT-calculated affinities.
Confirmed that increased nucleophilicity corresponds to higher affinity values.
Abstract
Nucleophilicities of eight vinyl azides were determined (in CH 2 Cl 2 and Cyrene) and shown to correlate linearly with DFT-calculated H 3 C + affinities.
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Cite This Study
Thiruvengetam et al. (Thu,) studied this question.