Theoretical study of solvent and substituent effects on the Diels-Alder reactions

Irani, Mehdi and Haghgu, Mohammad and Gholami, Mohammad Reza (2008) Theoretical study of solvent and substituent effects on the Diels-Alder reactions. In: 11th Iranian Physical Chemistry Seminar-July 2008.

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Abstract

The Diels-Alder (DA) reactions are important in forming carbon- carbon (C-C) bonds for organic chemists. These types of reactions can proceed in gas or solution phases. The DA reactions are concerted and do not involve prominent charge distribution in transition state. Therefore solvent effects on these reactions must be negligible, but these reactions are dramatically accelerated in water solvent. These effects can be recognized by frontier molecular orbital (FMO) theory. In this work we studied solvent and substitute effects on two series of reactions. The first one is the reactions of 1,4-Benzoquinone with 2-methyl-5-isopropylcyclohexa-1,3-diene (Reaction 1) and 1-methyl-4-isopropylcyclohexa-1,3-diene (Reaction 2). The experimental results show that the rates of these reactions in water are more than THF [1]. The second series of reactions is the reactions of 1,4-Benzoquinone with cyclopentadiene (Reaction 3), methylcyclopentadiene (Reaction 4) and 1,2,3,4,5- pentamethylcyclopentadiene (Reaction 5). Experimental results show that the relative rate constants in water solvent increase in the order of Reaction 5 > 4 > 3(in other word with adding of donating groups) [2].

Item Type: Conference or Workshop Item (Poster)
Persian Title: Theoretical study of solvent and substituent effects on the Diels-Alder reactions
Persian Abstract: -
Subjects: Divisions > Conferences > 11th Iranian Physical Chemistry Seminar- July 2008
Conferences > 11th Iranian Physical Chemistry Seminar- July 2008
Divisions: Conferences > 11th Iranian Physical Chemistry Seminar- July 2008
Subjects > Conferences > 11th Iranian Physical Chemistry Seminar- July 2008
Date Deposited: 17 Jun 2019 05:04
Last Modified: 17 Jun 2019 05:04
URI: http://repository.uma.ac.ir/id/eprint/6794

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