On the photochemical reaction of pyridinium salts with nucleophiles

Maurizio D'Auria

doi:10.1007/s43630-021-00070-6

On the photochemical reaction of pyridinium salts with nucleophiles

Photochem Photobiol Sci. 2021 Jul;20(7):923-926. doi: 10.1007/s43630-021-00070-6. Epub 2021 Jun 30.

Author

Maurizio D'Auria¹

Affiliation

¹ Dipartimento Di Scienze, Università Della Basilicata, Viale dell'Ateneo Lucano 10, 85100, Potenza, Italy. maurizio.dauria@unibas.it.

PMID: 34191256
DOI: 10.1007/s43630-021-00070-6

Abstract

DFT calculations on the photochemical reaction of 1-n-N-butylpyridinium salt in water with hydroxide anion is in agreement with a singlet state process where the S₂ state at λ = 253 nm can be converted into a Dewar isomer (2-butyl-2-azabicyclo[2.2.0]hexa-2,5-dien-2-yl cation). The Dewar isomer can react with hydroxide anion giving the product, 6-n-butyl-6-azabicyclo[3.1.0]hex-3-en-2-ol.

Keywords: Benzvalene isomer; Dewar isomer; Photochemistry; Pyridinium salts; Reaction with nucleophiles.