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Letters in Organic Chemistry

Author(s): Maurizio D’Auria*

DOI: 10.2174/1570178619666220210102829

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The Photoreaction of Pyrylium Cation with Water: A DFT Study

Page: [739 - 742] Pages: 4

  • * (Excluding Mailing and Handling)

Abstract

The photochemical reaction of pyrylium cation with water to give a cyclopentene derivative has been studied at the DFT/B3LYP/6-31G+(d,p) level of theory. The calculation is in agreement with an electrocyclic disrotatory reaction from the S1 singlet excited state, giving a cyclopentene epoxide cation that can react with very low activation energy (2 kJ mol-1) with water to give the corresponding adduct. CASSCF calculations allowed to identify a conical intersection in the S1 state, giving the cyclopentene epoxide cation.

Keywords: Pyrylium cation, photochemistry, isomerization reactions, water, DFT, CASSCF.

Graphical Abstract

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