Journal of Organic Chemistry p. 3710 - 3719 (2011)
Update date:2022-08-11
Topics:
Ma, Jiani
Li, Ming-De
Phillips, David Lee
Wan, Peter
Nanosecond time-resolved resonance Raman (ns-TR3) spectroscopy was employed to investigate the photoinduced reactions of 3-(hydroxymethyl) benzophenone (1) in acetonitrile, 2-propanol, and neutral and acidic aqueous solutions. Density functional theory calculations were utilized to help the interpretation of the experimental spectra. In acetonitrile, the neutral triplet state 1 [denoted here as (m-BPOH)3] was observed on the nanosecond to microsecond time scale. In 2-propanol this triplet state appeared to abstract a hydrogen atom from the solvent molecules to produce the aryphenyl ketyl radical of 1 (denoted here as ArPK of 1), and then this species underwent a cross-coupling reaction with the dimethylketyl radical (also formed from the hydrogen abstraction reaction) to form a long-lived light absorbing transient species that was tentatively identified to be mainly 2-(4-(hydroxy(3- (hydroxymethyl)phenyl)methylene)cyclohexa-2,5-dienyl)propan-2-ol. In 1:1 H 2O:CH3CN aqueous solution at neutral pH, (m-BPOH) 3 reacted with water to produce the ArPK of 1 and then underwent further reaction to produce a long-lived light absorbing transient species. Three photochemical reactions appeared to take place after 266 nm photolysis of 1 in acidic aqueous solutions, a photoreduction reaction, an overall photohydration reaction, and a novel photoredox reaction. TR3 experiments in 1:1 H2O:CH3CN aqueous solution at pH 2 detected a new triplet biradical species, which is associated with an unusual photoredox reaction. This reaction is observed to be the predominant reaction at pH 2 and seems to face competition from the overall photohydration reaction at pH 0.
View MoreShandong Yuanli Science and Technology Co., Ltd.
Contact:86-0536-6777557
Address:Zhuliu Industiral Park,Changle County
WEIFANG RICHEM INTERNATIONAL LTD
Contact:86-536-2222176
Address:weifang,shandong
Jinan Jianfeng Chemical Co., Ltd
Contact:0086-531-88110457
Address:sales01(-a-t-)pharmachemm{dot}c+o+m
Wuhan Benjamin Pharmaceutical Chemical Co.,Ltd
Contact:86-27-52341789
Address:Room 1518 B suite, optical valley time square, No 111 Guanshan Road, Hongshan District,Wuhan,Hubei Province,China.
Jiangsu Chunjiang AgroChemical Co.,Ltd.
Contact:+86-13817348163
Address:Panjiawan 84, Zhixi Town, Jintan City, China
Doi:10.1016/S0040-4039(00)78764-8
(1976)Doi:10.1134/S1070428006100186
(2006)Doi:10.1039/c8dt02838a
(2018)Doi:10.1103/PhysRevB.52.2032
()Doi:10.1016/j.tet.2009.06.036
(2009)Doi:10.1021/jp9822236
(1998)