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Photochemistry of 1- and 2-Naphthols and Their Water Clusters : The Role of 1 ππ*(La ) Mediated Hydrogen Transfer to Carbon Atoms


Novak, Jurica; Prlj, Antonio; Basarić, Nikola; Corminboeuf, Clémence; Došlić, Nađa
Photochemistry of 1- and 2-Naphthols and Their Water Clusters : The Role of 1 ππ*(La ) Mediated Hydrogen Transfer to Carbon Atoms // Chemistry : a European journal, 23 (2017), 34; 8244-8251 doi:10.1002/chem.201700691 (međunarodna recenzija, članak, znanstveni)


Naslov
Photochemistry of 1- and 2-Naphthols and Their Water Clusters : The Role of 1 ππ*(La ) Mediated Hydrogen Transfer to Carbon Atoms

Autori
Novak, Jurica ; Prlj, Antonio ; Basarić, Nikola ; Corminboeuf, Clémence ; Došlić, Nađa

Izvornik
Chemistry : a European journal (0947-6539) 23 (2017), 34; 8244-8251

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Excited state hydrogen transfer ; hydrogen/deuterium exchange ; naphthols ; photochemistry ; water clusters

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (Nikola Basarić, )
HRZZ-IP-2016-06-1142 - Svjetlo na molekulama: istraživanje spregnute elektronske i nuklearne dinamike (Nađa Došlić, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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