Related Experiment Video
Updated: Jul 14, 2026

Application of Electrophysiology Measurement to Study the Activity of Electro-Neutral Transporters
Published on: February 3, 2018
Experimental and theoretical characterization of the 3,5-didehydrobenzoate anion: a negatively charged meta-benzyne
Jason M Price1, Katrina Emilia Nizzi, J Larry Campbell
1Department of Chemistry, Purdue University, West Lafayette, IN 47907-1393, USA.
Abstract:
A negatively charged analogue of meta-benzyne, 3,5-didehydrobenzoate, was synthesized in a Fourier transform ion cyclotron resonance mass spectrometer, and its reactivity was compared to that of the same ion generated previously in a flowing afterglow apparatus and to its positively charged cousin, N-(3,5-didehydrophenyl)-3-fluoropyridinium. 3,5-Didehydrobenzoate was found to react as a nucleophile with electrophilic reagents. In contrast, N-(3,5-didehydrophenyl)-3-fluoropyridinium does not react with the same electrophilic reagents but reacts instead with nucleophilic reagents. Neither ion is able to abstract hydrogen atoms from typical hydrogen atom donors. The absence of any radical reactivity for these meta-benzynes is consistent with predictions that radical reactions of singlet biradicals should be hindered as compared to their monoradical counterparts. High-level calculations predict that the carboxylate moiety does not significantly perturb the singlet-triplet splitting of 3,5-didehydrobenzoate relative to the parent meta-benzyne.
Related Concept Videos
Electron Behavior
Ions and Ionic Charges
Ionic Bonding and Electron Transfer
Electron Behavior
Electrons Orbit the Nucleus
Electrons are found in specific locations outside of the nucleus. The shell in which an electron resides indicates the general energy level of the electron: those closer to the nucleus have less energy,...
Electrochemical Systems
The Electrical Double Layer

