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Intramolecular N···F Pnictogen Bond Mitigates the Explosive Behavior of Azido‐L‐Phenylalanines

Year: 2025

Type: article

Abstract: Organic azides are versatile intermediates but are plagued by intrinsic instability and potential explosiveness. Here, it is shown that fluorinated azido‐L‐phenylalanines display unexpected stability, arising from adjacent fluorine atoms that enforce intramolecular pnictogen bonding. Single‐crystal X‐ray diffraction reveals an intramolecular N···F pnictogen bond that orients the azide group and enhances molecular stability. Comparison with nonfluorinated analogs underscores the stabilizing effect of fluorine substitution in mitigating explosive decomposition. Quantum chemical and bond critical point analyses corroborate the stabilizing role of the N···F pnictogen bond.

Source: ChemistryEurope

DOI: 10.1002/ceur.202500371

Authors: Andrea Pizzi, Eleonora Veronese, Nicola Demitri, Marco Saccone, Pierangelo Metrangolo, Giancarlo Terraneo

Institutions: Politecnico di Milano, Elettra-Sincrotrone Trieste S.C.p.A., Università degli Studi del Piemonte Orientale “Amedeo Avogadro”

Language: English

Topic: Crystallography and molecular interactions

Subfield: Physical and Theoretical Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

OpenAlex ID: W7105991317

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Cites: 44

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