Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate

Authors

Ali Ramazani Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran

Ali Souldozi Department of Chemistry, Urmia Branch, Islamic Azad University, Urmia, Iran

Hooriye Yahyaei Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran

Masoome Sheikhi Sheikhi Young Researchers and Elite Club, Gorgan Branch, Islamic Azad University, Gorgan, Iran

Sang Woo Joo School of Mechanical Engineering, Yeungnam University, Gyeongsan 712-749, Republic of Korea

Abstract:

Dimethyl (z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butenedioate has been synthesized using one-pot three component reaction between N-isocyaniminotriphenylphosphorane (Ph3PNNC), 3-methylcyclopentene-1,2-dione and dimethyl acetylenedicarboxylate. Also, optimized geometry and nuclear magnetic resonance ( NMR ) of the title compound are evaluated using HF and B3LYP methods and 6-311+G(d) basis set. Moreover, the 1H and 13C NMR chemical shift values of the molecule are calculated and compared with experimental results. Frontier molecular orbitals (FMOs), total density of states (DOS), electronic properties, natural charges, NMR parameters and NBO analysis for product were calculated by theoretical calculations. Finally, molecular electrostatic potential (MEP) surface is obtained for understanding the active regions of molecule.

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Journal title

Iranian Chemical Communication

volume 5 issue Issue 4, pp. 364-493

pages 449- 470

publication date 2017-10-01

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Keywords

N-Isocyaniminotriphenylphosphorane (Ph3PNNC) one-pot DFT NBO analysis electronic properties

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