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The mechanistic study of reaction between N-benzoyl carbamates and aliphatic/aromatic amines for synthesis of substituted N-benzoyl urea derivatives: a DFT approach

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Abstract

A thorough investigation on whether a stepwise or a concerted pathway is involved in the synthesis of substituted N-benzoyl urea derivatives by reaction of substituted N-benzoylcarbamates and aliphatic/aromatic amines using density functional theory (DFT) calculations at B3LYP/6–31 + G (d,p) level of theory has been reported. The study of effects of nature of leaving group present in N-benzoylcarbamate, structure of amines, and solvents on the reaction showed that the choice of reaction mechanism involved depends upon the nature of leaving group present on N-benzoylcarbamate. The effect of structure of amine on reaction mechanism depends upon the type of leaving group present on N-benzoylcarbamate. We have also observed that the reaction between aliphatic/aromatic amine with phenyl benzoylcarbamate is thermodynamically more favorable, while a reaction between phenyl/methyl benzoylcarbamates with methylamine is more preferred. The effect of polar solvent water and non-polar solvent toluene on reaction mechanism was also investigated to account the interactions of solvent molecules with polar transition states at the same level of theory.

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  1. P.G. Department of Chemistry, M.M. Modi College, Patiala, Punjab, 147001, India

    Harjinder Singh

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Correspondence to Harjinder Singh.

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Singh, H. The mechanistic study of reaction between N-benzoyl carbamates and aliphatic/aromatic amines for synthesis of substituted N-benzoyl urea derivatives: a DFT approach. Struct Chem 30, 37–51 (2019). https://doi.org/10.1007/s11224-018-1171-8

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  • DOI: https://doi.org/10.1007/s11224-018-1171-8

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