Intramolecular photoinduced proton transfer in 2-(2-aminophenyl)-4H-3,1-benzoxazin-4-ones with different electron-withdrawing N-substituents View Full Text


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Article Info

DATE

2009-03-20

AUTHORS

M. N. Khimich, E. A. Birgen, B. M. Bolotin, B. M. Uzhinov

ABSTRACT

Fluorescence spectra of N-substituted 2-(2-aminophenyl)-4H-3,1-benzoxazin-4-ones consist of two bands, the long-wavelength band with anomalous Stokes shift, which corresponds to the emission of the product of intramolecular photoinduced proton transfer, and the short-wavelength band belonging to the form in which proton transfer does not occur. It is assumed that there is equilibrium between two planar rotamers in the ground state: one with the N-H…N hydrogen bond in which the intramolecular photoinduced proton transfer occurs and the other with the N-H…O bond, which does not experience hydrogen transfer. According to ab initio quantum-chemical calculations, the potential energy of proton transfer in the first excited singlet state has a potential barrier of 2.1–26.8 kJ/mol depending on the electron-withdrawing ability of the substituent on the amino group. More... »

PAGES

123-128

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s001814390902009x

DOI

http://dx.doi.org/10.1134/s001814390902009x

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1039245578


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