2012
DOI: 10.1134/s1070363212050143
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Kinetics of acylation of cyclohexylamine with substituted phenyl benzoates

Abstract: Kinetics of acylation of cyclohexylamine with nitro-substituted phenyl benzoates is studied in water solutions of 2-propanol and dioxane. By means of RHF/6-31G* method quantum-chemical simulation of ester molecules and of cyclohexylamine solvatocomplexes was carried out. On the basis of correlation of rate constants and LUMO energies of esters and population of 2p z -orbitals of carbon atom of the acyl group a conclusion on the orbital control of the reactions was made.An interest to the products of acylation … Show more

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“…For equal amounts of water in the system the values of k for all studied reactions in the mixture water-dioxane are considerably larger than the k values for the same reactions in aqueous 2-propanol (Tables 1-3). The accelerating effect of aqueous dioxane as compared to aqueous 2-propanol on the rate constants of Nacylation was observed also in other reactions, for example, in the reactions of ammonia, aliphatic amines and α-amino acids with esters and sulfonyl chlorides [7,[10][11][12][13].…”
mentioning
confidence: 87%
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“…For equal amounts of water in the system the values of k for all studied reactions in the mixture water-dioxane are considerably larger than the k values for the same reactions in aqueous 2-propanol (Tables 1-3). The accelerating effect of aqueous dioxane as compared to aqueous 2-propanol on the rate constants of Nacylation was observed also in other reactions, for example, in the reactions of ammonia, aliphatic amines and α-amino acids with esters and sulfonyl chlorides [7,[10][11][12][13].…”
mentioning
confidence: 87%
“…2), which is indicative of an important role of specific solvation of amines and transition states of the reaction of acylation. The solvation of the acylation reagents in the reaction of the acyl group transfer, according to the available data [7,[10][11][12][13], plays a subordinate role. Table 3 presents the results of the kinetic study of the reactions of piperidine and morpholine with compounds I and II in the system water (40 wt %)dioxane.…”
mentioning
confidence: 99%