Quantum chemical studies on the reactivity of oxazole derivatives
- Autores: Hosseinzadeh B.1,2, Eskandari K.3, Zarandi M.4, Asli R.1
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Afiliações:
- Department of Chemistry
- Chemical Engineering Department
- Young Researchers and Elites Club, Shahrekord Branch
- Young Researchers and Elites Club, Qom Branch
- Edição: Volume 90, Nº 11 (2016)
- Páginas: 2202-2210
- Seção: Structure of Matter and Quantum Chemistry
- URL: https://journals.rcsi.science/0036-0244/article/view/168950
- DOI: https://doi.org/10.1134/S0036024416110042
- ID: 168950
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Resumo
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 fk- values at the N-position are small in case of electron-withdrawing substituents, resulting a preferred N-position for hard reactions. In contrast, large fk- 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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Sobre autores
Behzad Hosseinzadeh
Department of Chemistry; Chemical Engineering Department
Autor responsável pela correspondência
Email: behzad.hosseinzadeh89@gmail.com
Irã, Yasouj, 75918-74831; Behshahr
Khalil Eskandari
Young Researchers and Elites Club, Shahrekord Branch
Email: behzad.hosseinzadeh89@gmail.com
Irã, Shahrekord
Maryam Zarandi
Young Researchers and Elites Club, Qom Branch
Email: behzad.hosseinzadeh89@gmail.com
Irã, Qom
Reza Asli
Department of Chemistry
Email: behzad.hosseinzadeh89@gmail.com
Irã, Yasouj, 75918-74831