Photolysis of N-phenylhydroxylamine: a novel photochemical disproportionation reaction in N-O bond cleavage assisted by hydrogen bonding

被引:7
|
作者
White, RC [1 ]
Selvam, T
Ihmels, H
Adam, W
机构
[1] Sam Houston State Univ, Dept Chem, Huntsville, TX 77341 USA
[2] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
关键词
photolysis; N-phenylhydroxylamine; hydrogen bonding; azobenzene;
D O I
10.1016/S1010-6030(99)00019-2
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The photochemistry of N-phenylhydroxylamine (9) has been examined in the solution phase and in the solid state. The major products are aniline and nitrosobenzene. The nitrosobenzene quickly reacts with 9 to generate azoxybenzene and with aniline to produce azobenzene. The quantum yields for the disappearance of 9 are reasonably high (0.25-0.29) and suggest that the photochemical reactions proceed from a hydrogen-bonded dimer. (C) 1999 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:7 / 10
页数:4
相关论文
共 50 条
  • [1] N-O bond cleavage and various bonding modes of the nitrato ligand in rhodium complexes
    Han, Won Seok
    Lee, Soon W.
    2003, Elsevier S.A. (348)
  • [2] Cathodic N-O Bond Cleavage of N-Alkoxy Amide
    Sato, Eisuke
    Ogita, Sayaka
    Mitsudo, Koichi
    Suga, Seiji
    ELECTROCHEMISTRY, 2023, 91 (11)
  • [3] METAL-ASSISTED CARBONYLATION OF AN N-O BOND
    BREEDLOVE, BK
    GARGULAK, JD
    GLADFELTER, WL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 372 - INOR
  • [4] N-O bond cleavage in O-silylated oximes by reaction with a titanocene-alkyne complex
    Tillack, A
    Arndt, P
    Spannenberg, A
    Kempe, R
    Rosenthal, U
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1998, 624 (04): : 737 - 740
  • [5] N-O bond cleavage during the deprotonation of N,O-bis(trimethylsilyl)hydroxylamine
    Venugopal, Ajay
    Willner, Alexander
    Mitzel, Norbert W.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2008, 63 (03): : 339 - 341
  • [6] REACTION OF TRIMETHYLSILYL AZIDE WITH C=N-O BOND
    NISHIYAMA, K
    MIYATA, I
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (08) : 2419 - 2420
  • [7] Cleavage of the N-O bond in substituted hydroxylamines under basic conditions
    Nikitin, KV
    Andryukhova, NP
    MENDELEEV COMMUNICATIONS, 2000, (01) : 32 - 33
  • [8] MECHANISM OF THE PYRENE-SENSITIZED PHOTOLYSIS OF N-(L-NAPHTHOYL)-O-(PARA-TOLUOYL)-N-PHENYLHYDROXYLAMINE
    SAKURAI, T
    INOMATA, K
    ISHIKAWA, T
    INOUE, H
    HOSHI, T
    OKUBO, J
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (11) : 4099 - 4105
  • [9] Mechanism of the benzophenone-sensitized photolysis of O-benzoyl-N-(1-naphthoyl)-N-phenylhydroxylamine in cationic micellar media
    Kaneko, T
    Tokue, T
    Kubo, K
    Sakurai, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1999, 72 (12) : 2771 - 2780
  • [10] N-O bond cleavage mechanism(s) in nitrous oxide reductase
    Ertem, Mehmed Z.
    Cramer, Christopher J.
    Himo, Fahmi
    Siegbahn, Per E. M.
    JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2012, 17 (05): : 687 - 698