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Kinetics, catalysis, and mechanism of isomerization of N ‐[(benzotriazol‐1‐yl)methyl]anilines into the benzotriazol‐2‐yl derivatives
Author(s) -
Katritzky Alan R.,
Rachwal Stanislaw,
Rachwal Bogumila,
Frankenfeld John W.
Publication year - 1995
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.550270406
Subject(s) - chemistry , isomerization , aniline , triethylamine , catalysis , kinetics , medicinal chemistry , acetic acid , reaction rate constant , photochemistry , organic chemistry , physics , quantum mechanics
The 1 H NMR technique was applied for the measurement of the isomerization rates of N ‐ethyl‐ N ‐[(benzotriazol‐1‐yl)methyl]aniline ( 4 ) and 4‐butyl‐ N ‐[(benzotriazol‐1‐yl)methyl]aniline ( 7 ) to the corresponding benzotriazol‐2‐yl isomers in dioxane‐d 8 at 35°C. The rate constants obtained for pure dioxane‐d 8 were 1.62 and 0.28 h −1 for 4 and 7 , respectively. For both compounds, addition to acetic acid to the dioxane solutions accelerated the isomerizations whereas addition of triethylamine retarded it strongly. Addition of water slowed the isomerization of 4 but accelerated that of 7 : the different effects operating in the two cases are discussed and rationalized. © 1995 John Wiley & Sons, Inc.