IMPACT OF LEWIS ACID CATALYST ON THE REGIOSELECTIVITY AND KINETICS OF 1, 3-DIPOLAR CYCLOADDITION REACTION OF AZIDOBENZENE WITH ACROLEIN: A THEORETICAL STUDY USING DFT

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SHAMS F.; EMAMIAN S.R.; ZAHEDI E.

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Paper Information

Journal: JOURNAL OF PHYSICAL AND THEORETICAL CHEMISTRY Year:2013 | Volume:10 | Issue:2 Page(s): 91-98

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Title

IMPACT OF LEWIS ACID CATALYST ON THE REGIOSELECTIVITY AND KINETICS OF 1, 3-DIPOLAR CYCLOADDITION REACTION OF AZIDOBENZENE WITH ACROLEIN: A THEORETICAL STUDY USING DFT

Author(s)

SHAMS F. | EMAMIAN S.R. | ZAHEDI E. | Issue Writer Certificate

Keywords

1Q2

3-DIPOLAR CYCLOADDITIONQ2

AZIDOBENZENEQ2

ACROLEINQ2

REGIOSELECTIVITYQ2

DFT REACTIVITY INDEXESQ1

PARR FUNCTIONSQ1

Abstract

In the present work, impact of Lewis acid (LA) catalysts BF3, BCl3, and BBr3 on the kinetics and REGIOSELECTIVITY of 1, 3-DIPOLAR CYCLOADDITION (1, 3-DC) reaction between AZIDOBENZENE and ACROLEIN was theoretically studied using B3LYP/6-31G* level. Our results indicate while the uncatalyzed 1, 3-DC reaction under investigation takes place via a non-polar, non-regioselective, and low asynchronous process, the LA catalyzed 1, 3-DC reaction takes place via a polar, regioselective, and high asynchronous process. In addition, the barrier height of the studied 1, 3-DC reaction is considerably reduced in the presence of LA catalysts, and the catalytic activity of LAs in order to increase the electrophilicity character of ACROLEIN and, consequently, to reduce barrier height of reaction, is increased with the increase of halogen atom size; BBr3> BCl3> BF3. REGIOSELECTIVITY in these LA catalyzed 1, 3-DC reactions appears to be controlled by steric repulsion effects between the LA catalyst and the azide phenyl substituent instead of the electronic effects.

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APA: Copy

SHAMS, F., EMAMIAN, S.R., & ZAHEDI, E.. (2013). IMPACT OF LEWIS ACID CATALYST ON THE REGIOSELECTIVITY AND KINETICS OF 1, 3-DIPOLAR CYCLOADDITION REACTION OF AZIDOBENZENE WITH ACROLEIN: A THEORETICAL STUDY USING DFT. JOURNAL OF PHYSICAL AND THEORETICAL CHEMISTRY, 10(2), 91-98. SID. https://sid.ir/paper/207694/en

Vancouver: Copy

SHAMS F., EMAMIAN S.R., ZAHEDI E.. IMPACT OF LEWIS ACID CATALYST ON THE REGIOSELECTIVITY AND KINETICS OF 1, 3-DIPOLAR CYCLOADDITION REACTION OF AZIDOBENZENE WITH ACROLEIN: A THEORETICAL STUDY USING DFT. JOURNAL OF PHYSICAL AND THEORETICAL CHEMISTRY[Internet]. 2013;10(2):91-98. Available from: https://sid.ir/paper/207694/en

IEEE: Copy

F. SHAMS, S.R. EMAMIAN, and E. ZAHEDI, “IMPACT OF LEWIS ACID CATALYST ON THE REGIOSELECTIVITY AND KINETICS OF 1, 3-DIPOLAR CYCLOADDITION REACTION OF AZIDOBENZENE WITH ACROLEIN: A THEORETICAL STUDY USING DFT,” JOURNAL OF PHYSICAL AND THEORETICAL CHEMISTRY, vol. 10, no. 2, pp. 91–98, 2013, [Online]. Available: https://sid.ir/paper/207694/en

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