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KINETIC STUDY OF THE REACTIONS OF2‐AMINO‐5‐CHLOROBENZOPHENONE WITH HCl in MeOH–H 2 O
Author(s) -
Nudelman N. Sbarbati,
de Waisbaum R. G.
Publication year - 1997
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199702)10:2<97::aid-poc865>3.0.co;2-w
Subject(s) - chemistry , reaction rate constant , reaction rate , medicinal chemistry , order of reaction , kinetics , computational chemistry , organic chemistry , catalysis , physics , quantum mechanics
The reaction of 2‐amino‐5‐chlorobenzophenone (1) with 0·5–2 M HCl was studied in 1:1 (v/v) MeOH–H 2 O at 60 and 80 °C. Products that were isolated were characterized as 2‐( N ‐methylamino‐5‐chlorobenzophenone) (2), 2‐ amino‐3,5‐dichlorobenzophenone (3), 2‐ N ‐methylamino‐3,5‐dichlorobenzophenone (4), 2‐( N , N )‐dimethylamino‐5‐ chlorobenzophenone (5), 2,4‐dichloro‐10‐methyl‐9,10‐acridinone (6) and 2,4‐dichloro‐9,10‐acridinone (7). The rates of reaction of 1 and the rates of formation of 2–5 were measured at several HCl concentrations. The methyl transfers, the chlorination and the cyclization reactions that give rise to 2–7 were unexpected under the present reaction conditions. A set of differential equations was proposed in order to calculate the rate constants for each step of this complex reaction. The proposed reaction scheme also takes into account the reaction 2→1 and permits the calculation of the rate constants for this reversible reaction. The experimental values of the rate constants for reaction of 1 were compared with those for 2 under the same reaction conditions, in order to evaluate the importance of the methyl group on the methyl transfer reactions; it was found that the methyl group is not required for the unexpected reaction to occur. © 1997 by John Wiley & Sons, Ltd.