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Intramolecular photoinduced proton transfer in 2-(2-aminophenyl)-4H-3,1-benzoxazin-4-ones with different electron-withdrawing N-substituents
| Content Provider | Semantic Scholar |
|---|---|
| Author | Khimich, Mikhail N. Birgen, E. A. Bolotin, B. M. Uzhinov, Boris M. |
| Copyright Year | 2009 |
| 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. |
| Starting Page | 123 |
| Ending Page | 128 |
| Page Count | 6 |
| File Format | PDF HTM / HTML |
| DOI | 10.1134/S001814390902009X |
| Alternate Webpage(s) | https://page-one.springer.com/pdf/preview/10.1134/S001814390902009X |
| Alternate Webpage(s) | https://doi.org/10.1134/S001814390902009X |
| Volume Number | 43 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
