Naslov
Electronic Structure and Stability of Benzotriazoles

Autori
Novak, Igor ; Abu-Izneid, T. ; Kovač, Branka ; Klasinc, Leo

Izvornik
Journal of Physical Chemistry A (1089-5639) 113 (2009), 35; 9751-9756

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

Ključne riječi
photoelectron spectra ; benzotriazoles ; DFT ; OVGF

Sažetak
The electronic structures and relative stabilities of N-substituted benzotriazoles (BtR) have been studied by UV photoelectron spectroscopy (UPS) and high-level ab initio methods. We show that the UPS spectrum of 1H-benzotriazole corresponds to a mixture of tautomers. The N-substituent effects in benzotriazoles were shown to depend on the mode of attachment of the substituent to the Bt residue. We have estimated the conjugation effects between benzene and triazole rings in N-substituted benzotriazoles by using isodesmic reactions and high-level composite ab initio methods. The 2H-benzotriazoles (Bt2R) appear to be stabilized upon ring conjugation while on the other hand the 1H-benzotriazoles (Bt1R) are destabilized. The electronic structure of benzotriazoles can be related to photocycloaddition reactions and to regioselectivity exhibited during nitration.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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