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EPR and NMR experiments on a quinazolinone-based Schiff's base in DMSO solution showed that irradiation with UV light (365 nm) leads to photochemically-induced isomerization from the anti - to the higher-energy syn -form around the -N-N[double bond, length as m-dash] linkage. The anti - to syn -isomerization was relatively fast, and the maximum amount of conversion detected (25%) was reached within 10 min; thermodynamic equilibrium re-established itself in about 15 min. DFT calculations were performed on the investigated compound and small model systems, and reproduced the experimental fact of the anti -conformer being lower in energy than the syn . Theoretical analysis of excited states, including visualisation of natural transition orbitals, identified possible pathways for syn - anti isomerisation, although the details vary with π-system size, making the use of small models of limited utility. The investigated compound probably isomerises through the third singlet excited state (S 3 ), a π-π* excitation, relaxing through S 2 , also a π-π* state.

Photochemical anti–syn isomerization around the –N–N bond in heterocyclic imines