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Quantum chemical studies on the reactivity of oxazole derivatives

  • Structure of Matter and Quantum Chemistry
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Abstract

The quantum chemical study of the reactivity of a series of oxazole derivatives substituted at 2, 4, and 5 positions was performed using B3LYP/6-311++G(d,p) and MP2/6-311++G(d,p) levels of theory. Different substituents have been applied to cover a wide range of electronic effects. On the basis of Fukui functions, oxazole derivatives in the gas phase are found to be suitable nucleophilic sites. For the most of studied substituents, it was observed that the calculated Fukui function f - k values at the N-position are small in case of electron-withdrawing substituents, resulting a preferred N-position for hard reactions. In contrast, large f - k values in case of electron-donating groups show a preferred N-position for soft reactions. These two local reactivity descriptors predicted the reactivity of the electron-rich oxazoles sequence to be 2-substituted oxazoles > 5-substituted oxazoles > 4-substituted oxazoles, where due to resonance effect, the reactivity toward electrophilic attack at the pyridine nitrogen atom is enhanced by electron donor substituents.

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Authors and Affiliations

  1. Department of Chemistry, Yasouj University, Yasouj, 75918-74831, Iran

    Behzad Hosseinzadeh & Reza Asli

  2. Chemical Engineering Department, Mazandaran University of Science and Technology, Behshahr, Iran

    Behzad Hosseinzadeh

  3. Young Researchers and Elites Club, Shahrekord Branch, Islamic Azad University, Shahrekord, Iran

    Khalil Eskandari

  4. Young Researchers and Elites Club, Qom Branch, Islamic Azad University, Qom, Iran

    Maryam Zarandi

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  1. Behzad Hosseinzadeh
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  2. Khalil Eskandari
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  3. Maryam Zarandi
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  4. Reza Asli
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Correspondence to Behzad Hosseinzadeh.

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Hosseinzadeh, B., Eskandari, K., Zarandi, M. et al. Quantum chemical studies on the reactivity of oxazole derivatives. Russ. J. Phys. Chem. 90, 2202–2210 (2016). https://doi.org/10.1134/S0036024416110042

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  • DOI: https://doi.org/10.1134/S0036024416110042

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