Difference in the Reactions of N-Methylhydroxylamine and N-Phenylhydroxylamine with Nitrosobenzene

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Abstract

The reaction of nitrosobenzene with <i>N</i>-methylhydroxylamine was studied. The pH-rate profile exhibits a negative break at between pH 0.5 and 3.0, which is considered to be caused by a change in the rate-determining step of the reaction from an attack of the amine on nitrosobenzene at low pH, to the dehydration of an addition intermediate previously formed between the reagents at higher pH. This behavior is different from that of the reaction between <i>N</i>-phenylhydroxylamine and nitrosobenzene where, over the entire pH range, the only rate-determining step is dehydration of the addition intermediate. This fact confirms the special behavior of phenylhydroxylamine as a nucleophile, as was observed in its reactions with aromatic aldehydes.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 71(10), 2381-2385, 1998-10-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008937416
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4583843
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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