Interpretation of Nucleophilic α- and their relative β-, γ- and δ-Effects from Recognition of Tetrel Bonding Interaction: An Experimental Validation in Solution through Fluorometry

The data consists of NMR spectra and output for all calculations performed in the corresponding article. Theoretical Calculation. Herein we reported a simple and rapid strategy to validate the nucleophilicity and nucleophilic α-effect from simple steady state fluorescence measurements at room temperature with minimal sample and time requirements using a convenient fluorophore featuring an σ-hole region. The key point was the occurrence of a tetrel bond (TtB) between σ/π-hole region (A-acceptor) of the fluorophore with nucleophilic side of nucleophile. That TtB promoted a selective quenching that was dependent on the nucleophilicity of the nucleophile. Other key point was the existence of an ICT mechanism into fluorophore upon excitation, which enhanced the selectivity and strength of the quenching response. A broad number of nucleophiles from anionic species to neutral nucleophiles was analyzed. The occurrence of the TtB was theoretically and experimentally supported. Also, we introduced the concept of “nucleophilic β, γ- and δ-effects” for interpreting the over-nucleophilicity of some “β-, γ- and δ-nucleophiles”. A general interpretation of the origin of the anomalous nucleophilic effects based on the extra stabilization of transition-state and the high magnitude of HOMO energies was provided. Our strategy opens new perspective for quantifying the nucleophilicity and their anomalous effects based on the recognition of non-covalent interaction and using the fluorometry as key technique for detection. The data consisted of experimental NMR for supporting tetrel bond adduct between probe and iodide. Output documents with all details are available from calculation derived from tetrel bond between probe 3k with different nucleophiles as well as simple .log document from optimization and HOMO/LUMO output for all studied nucleophiles at different theoretical approach. Also, simulation transition state between probe and nucleophile adduct, their optimization output as .log document are found.