Mechanism of the benzidine rearrangement. Kinetic isotope effects and transition states. Evidence for concerted rearrangement

When hydrazobenzene rearranges in acid solution, benzidine and diphenyline are formed. Nitrogen and carbon isotope effects were calculated for concerted and dissociative transition states for the formation of benzidine. These calculations are in excellent agreement with experiment for the concerted...

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Veröffentlicht in:	J. Am. Chem. Soc.; (United States) 1981-02, Vol.103 (4), p.955-956
Hauptverfasser:	Shine, Henry J, Zmuda, Henryk, Park, Koon Ha, Kwart, Harold, Horgan, Ann Gaffney, Collins, Clair, Maxwell, Brian E
Format:	Artikel
Sprache:	eng
Schlagworte:	400302 - Organic Chemistry- Isotope Effects- (-1987) AMINES AROMATICS BENZIDINE BETA DECAY RADIOISOTOPES BETA-MINUS DECAY RADIOISOTOPES CARBON 14 CARBON ISOTOPES CHEMICAL REACTION YIELD CHEMICAL REACTIONS DEUTERIUM EVEN-EVEN NUCLEI HYDROGEN ISOTOPES INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ISOTOPE EFFECTS ISOTOPES LIGHT NUCLEI NITROGEN 15 NITROGEN ISOTOPES NUCLEI ODD-EVEN NUCLEI ODD-ODD NUCLEI ORGANIC COMPOUNDS RADIOISOTOPES STABLE ISOTOPES YEARS LIVING RADIOISOTOPES YIELDS
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Beschreibung
Zusammenfassung:	When hydrazobenzene rearranges in acid solution, benzidine and diphenyline are formed. Nitrogen and carbon isotope effects were calculated for concerted and dissociative transition states for the formation of benzidine. These calculations are in excellent agreement with experiment for the concerted formation of benzidine and suggest that formation of diphenyline is a dissociative process. (DLC)
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja00394a047