We are pleased to share our latest publication in Physical Chemistry Chemical Physics:
Special congratulations to Bruno Piscelli and Caio Nascimento for the paper. This publication represents another step toward understanding the stereoelectronic effects that govern the chemistry of fluorinated strained molecules and their potential applications in organic synthesis.
In this work, we investigate how progressive fluorination markedly changes the structural and electronic properties of bicyclo[1.1.0]butanes (BCBs), a class of highly strained molecules that has attracted increasing interest as versatile building blocks in synthetic and medicinal chemistry. Using computational chemistry, we demonstrate that fluorination can reduce the inversion barrier of BCBs from approximately 64 kcal mol⁻¹ to just 3.6 kcal mol⁻¹ in the perfluorinated analogue, while simultaneously increasing their electrophilicity through substantial LUMO stabilization. The study also reveals how different fluorination patterns influence hyperconjugative interactions, providing a molecular-level understanding of the remarkable changes in stability and reactivity observed for these systems.
