58287-31-3Relevant academic research and scientific papers
Benzimidazole derivatives
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, (2008/06/13)
Disclosed are compounds represented by the following chemical formula (I) and pharmacologically acceptable salts thereof which are novel compounds useful as anticancer agents, antiviral agents or antimicrobial agents. STR1
Effects of N-Alkyl Substitution on the Formation and Rate-limiting Deprotonation of the Spiro-Meisenheimer Intermediate of Smiles Rearrangement of 2-(p-Nitrophenoxy)ethylamine, in Aqueous Solution
Knipe, Anthony C.,Sridhar, Narayan,Lound-Keast, Joseph
, p. 1893 - 1900 (2007/10/02)
For intramolecular rearrangement of 2-(p-nitrophenoxy)ethylamines to the corresponding 2-(p-nitro-anilino)ethanols the kinetic effects of N-alkyl substitution have been interpreted in terms of a mechanism whereby base-independent formation of a spiro-Meisenheimer intermediate is rate determined at high base concentrations but general-base-catalysed deprotonation of the intermediate (β 0.18-0.35) becomes rate determining at low base concentration.Reactions of the N-ethyl and N-isopropyl substrates are further complicated by a change to a specific-base-catalysed mechanism in ethanolamine buffers of high concentration; this observation requires that formation of the product by ring opening of the anionic spiro-Meisenheimer intermediate is not sensitive to general-acid catalysis.
