Photochemistry of 1- and 2-Naphthols and Their Water Clusters : The Role of 1 ππ*(La ) Mediated Hydrogen Transfer to Carbon Atoms (CROSBI ID 243561)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Novak, Jurica ; Prlj, Antonio ; Basarić, Nikola ; Corminboeuf, Clémence ; Došlić, Nađa
engleski
Photochemistry of 1- and 2-Naphthols and Their Water Clusters : The Role of 1 ππ*(La ) Mediated Hydrogen Transfer to Carbon Atoms
The computational analysis of the isomer-and conformer-dependent photochemistry of 1- and 2- naphthols and their microsolvated water clusters is motivated by their very different excited state reactivities. We present evidence that 1- and 2- naphthol follow distinct excited state deactivation pathways. The deactivation of 2- naphthols, 2-naphthol water clusters, as well as of the anti conformer of 1-naphthol is mediated by the optically dark (1)pi sigma* state. The dynamics of the (1)pi sigma* surface leads to the homolytic cleavage of the OH bond. On the contrary, the excited state deactivation of syn 1- naphthol and 1-naphthol water clusters follows an uncommon reaction pathway. Upon excitation to the bright (1)pi pi*(L-a) state, a highly specific excited state hydrogen transfer (ESHT) to carbon atoms C8 and C5 takes place, yielding 1, 8- and 1, 5-naphthoquinone methides. The ESHT pathway arises from the intrinsic electronic properties of the (1)pi pi*(L-a) state of 1-naphthols.
excited state hydrogen transfer ; hydrogen/deuterium exchange ; naphthols ; photochemistry ; water clusters
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Podaci o izdanju
23 (34)
2017.
8244-8251
objavljeno
0947-6539
1521-3765
10.1002/chem.201700691