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Theoretical and voltammetric studies on the electron detachment process of 2,3-dihydroquinazolin-4(1H)-ones

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Abstract

Electronic and steric effects of the substituent on the 2-position of the heterocyclic ring of various 2-substituted 2,3-dihydroquinazolin-4(1H)-ones (DHQZ) were studied using voltammetric methods at a glassy carbon electrode in chloroform. Analysis of the results indicates that the electronic nature and the steric hindrance of the 2-substitution determine the effects on the oxidation peak potentials. The nature of the solvent also affects the electron detachment process in this study, which explains the extent of solvation of both the neutral DHQZ molecule and the ionic DHQZ·+ intermediate. Analysis of the computational results obtained at the density functional level of theory-B3LYP/6-31++G** level of theory suggests a mechanism in which the first electron removal occurs preferably from the N1 atom of both possible donor positions, N1 and N3 atoms. This process is followed by a fast proton removal from the 2-position of the heterocyclic ring, resulting in the formation of stable benzylic and also donor substituted radicals, which then undergo further oxidation to the quinazolin-4(3H)-ones. Computational studies in the gas phase and also in the bulk of solvent explain the effect of the nature of solvent on the readiness of the electron detachment process.

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Acknowledgments

We are thankful to the Research Council and Office of Graduate Studies of the University of Isfahan for their financial support, and to Prof. R. Karimi and Dr. A. Kiani for helpful discussion.

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Authors and Affiliations

  1. Department of Chemistry, University of Isfahan, 81746-73441, Isfahan, I. R. Iran

    Hamid Reza Memarian & Saeid Ebrahimi

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  1. Hamid Reza Memarian
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  2. Saeid Ebrahimi
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Correspondence to Hamid Reza Memarian.

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In memory of Prof. M. Rahimizadeh, University of Ferdowsi, who passed away on 24 March 2014.

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Memarian, H.R., Ebrahimi, S. Theoretical and voltammetric studies on the electron detachment process of 2,3-dihydroquinazolin-4(1H)-ones. Monatsh Chem 145, 1545–1554 (2014). https://doi.org/10.1007/s00706-014-1221-x

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  • DOI: https://doi.org/10.1007/s00706-014-1221-x

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