Excited-State Hydroxide Ion Release From a Series of Acridinol Photobases
作者： Yun Xie , Stefan Ilic , Sanja Skaro , Veselin Maslak , Ksenija D. Glusac
关键词: Reaction rate constant 、 Heterolysis 、 Chemical reaction 、 Butanol 、 Solvent 、 Marcus theory 、 Chemistry 、 Reaction coordinate 、 Hydroxide 、 Physical chemistry 、 Organic chemistry
摘要: The excited-state heterolysis of acridinol-based derivatives leads to the release OH– ion and formation corresponding acridinium cations. To evaluate parameters that control reaction barriers, kinetics from a series acridinol photobases were studied using transient absorption spectroscopy. rate constants obtained in three solvents (methanol, butanol, isobutanol), data modeled Marcus theory. intrinsic reorganization energies these fits found correlate well with solvent calculated dielectric continuum model, suggesting occurs along coordinate. Furthermore, ability photoinitiate chemical reactions was demonstrated Michael between dimethylmalonate nitrostyrene.
acs.org
sci-hub.se 参考文章(66)
Bradley J. Siwick, Huib J. Bakker, On the role of water in intermolecular proton transfer reactions Journal of the American Chemical Society. ,vol. 129, pp. 13412- 13420 ,(2007) , 10.1021/JA069265P
Xun Sun, Jian Ping Gao, Zhi Yuan Wang, Bicyclic guanidinium tetraphenylborate: a photobase generator and a photocatalyst for living anionic ring-opening polymerization and cross-linking of polymeric materials containing ester and hydroxy groups. Journal of the American Chemical Society. ,vol. 130, pp. 8130- 8131 ,(2008) , 10.1021/JA802816G
Stephen F. Nelsen, Dwight A. Trieber, Rustem F. Ismagilov, Yoshio Teki, Solvent effects on charge transfer bands of nitrogen-centered intervalence compounds. Journal of the American Chemical Society. ,vol. 123, pp. 5684- 5694 ,(2001) , 10.1021/JA003436N
D. B. Spry, A. Goun, K. Glusac, David E. Moilanen, M. D. Fayer, Proton Transport and the Water Environment in Nafion Fuel Cell Membranes and AOT Reverse Micelles Journal of the American Chemical Society. ,vol. 129, pp. 8122- 8130 ,(2007) , 10.1021/JA071939O
A.K. Chandra, V.Sreedhara Rao, An examination of the BEBO model with the results of ab initio calculations of a reaction series principles and practice of constraint programming. ,vol. 187, pp. 297- 303 ,(1994) , 10.1016/0301-0104(94)89012-9
Peter Wan, Keith Yates, Mary K. Boyd, Adiabatic photodehydroxylation of 9-phenylxanthen-9-ol. Observation of carbocation fluorescence in neutral aqueous solution The Journal of Organic Chemistry. ,vol. 50, pp. 2881- 2886 ,(1985) , 10.1021/JO00216A016
Cátia Parente Carvalho, Vanya D. Uzunova, José P. Da Silva, Werner M. Nau, Uwe Pischel, A photoinduced pH jump applied to drug release from cucurbit[7]uril Chemical Communications. ,vol. 47, pp. 8793- 8795 ,(2011) , 10.1039/C1CC12954F
Robert E. Minto, Paritosh K. Das, Laser flash photolysis study of photodehydroxylation phenomena of 9-phenylxanthen-9-ol and photobehavior of related intermediates. Enhanced electrophilicity of 9-phenylxanthenium cation singlet Journal of the American Chemical Society. ,vol. 111, pp. 8858- 8866 ,(1989) , 10.1021/JA00206A014
Noam Agmon, Dan Huppert, Asnat Masad, Ehud Pines, Excited-state proton transfer to methanol-water mixtures The Journal of Physical Chemistry. ,vol. 95, pp. 10407- 10413 ,(1991) , 10.1021/J100178A030
Dapeng Zhou, Renat Khatmullin, Janitha Walpita, Nicholas A. Miller, Hoi Ling Luk, Shubham Vyas, Christopher M. Hadad, Ksenija D. Glusac, Mechanistic Study of the Photochemical Hydroxide Ion Release from 9-Hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine Journal of the American Chemical Society. ,vol. 134, pp. 11301- 11303 ,(2012) , 10.1021/JA3031888