A COMPETITIVE DIELS-ALDER/1, 3-DIPOLAR CYCLOADDITION REACTION OF1-H-IMIDAZOLE 3-OXIDE TOWARD SULFONYL METHANE. A DFT STUDY ON THE ENERGETIC AND REGIOSELECTIVITY

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EMAMIAN SAEEDREZA

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Journal Paper

Paper Information

Journal: JOURNAL OF PHYSICAL AND THEORETICAL CHEMISTRY Year:2016 | Volume:12 | Issue:4 Page(s): 339-348

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Title

A COMPETITIVE DIELS-ALDER/1, 3-DIPOLAR CYCLOADDITION REACTION OF1-H-IMIDAZOLE 3-OXIDE TOWARD SULFONYL METHANE. A DFT STUDY ON THE ENERGETIC AND REGIOSELECTIVITY

Author(s)

EMAMIAN SAEEDREZA | Issue Writer Certificate

Keywords

DIELS-ALDER AND 1

3-DIPOLAR CYCLOADDITION REACTIONS

REGIOSELECTIVITY

DFT REACTIVITY INDICES

FMOS INTERACTION

PARR FUNCTIONS

Abstract

The dual diene/1,3-dipolar character of 1-H-imidazole 3-oxide, HIO 1, allows this compound to participate in a competitive Diels-Alder (DA)/1,3-dipolar cycloaddition (13DC) reaction toward C=S double bond of the electro-deficient sulfonyl methane SFM 2. The B3LYP/6-311++G(d,p) calculated relative Gibbs free energies indicate that among the studied 13DC and DA reactions, former is completely preferred over the latter in the gas phase as well as in the presence of dichloromethane (DCM). This 13DC reaction takes place through a one-step mechanism to generate corresponding five-membered cycloadduct via a quite C1-S5 regioselective fashion which is controlled by the HOMO(HIO 1)- LUMO(SFM 2) interaction. The aromatic character of HIO 1 which is lost along the studied cycloaddition reaction is responsible for the relatively high activation Gibbs free energies and the endergonic character of these thermodynamically reversible reactions. The quite C1-S5 REGIOSELECTIVITY, resulted from energetic studies, in the investigated 13DC reaction can be explained using calculated electrophilic and nucleophilic PARR FUNCTIONS at the reactive sites of reagents.

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APA: Copy

EMAMIAN, SAEEDREZA. (2016). A COMPETITIVE DIELS-ALDER/1, 3-DIPOLAR CYCLOADDITION REACTION OF1-H-IMIDAZOLE 3-OXIDE TOWARD SULFONYL METHANE. A DFT STUDY ON THE ENERGETIC AND REGIOSELECTIVITY. JOURNAL OF PHYSICAL AND THEORETICAL CHEMISTRY, 12(4), 339-348. SID. https://sid.ir/paper/676523/en

Vancouver: Copy

EMAMIAN SAEEDREZA. A COMPETITIVE DIELS-ALDER/1, 3-DIPOLAR CYCLOADDITION REACTION OF1-H-IMIDAZOLE 3-OXIDE TOWARD SULFONYL METHANE. A DFT STUDY ON THE ENERGETIC AND REGIOSELECTIVITY. JOURNAL OF PHYSICAL AND THEORETICAL CHEMISTRY[Internet]. 2016;12(4):339-348. Available from: https://sid.ir/paper/676523/en

IEEE: Copy

SAEEDREZA EMAMIAN, “A COMPETITIVE DIELS-ALDER/1, 3-DIPOLAR CYCLOADDITION REACTION OF1-H-IMIDAZOLE 3-OXIDE TOWARD SULFONYL METHANE. A DFT STUDY ON THE ENERGETIC AND REGIOSELECTIVITY,” JOURNAL OF PHYSICAL AND THEORETICAL CHEMISTRY, vol. 12, no. 4, pp. 339–348, 2016, [Online]. Available: https://sid.ir/paper/676523/en

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