Toward an understanding of the acceleration of Diels-Alder reactions by a pseudo-intramolecular process achieved by molecular recognition. A DFT study |
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Authors: | Domingo Luis R Aurell M José Arnó Manuel Saez José A |
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Institution: | Departamento de Química OrgAnica, Universidad de Valencia, Dr. Moliner 50, 46100 Burjassot, Valencia, Spain. domingo@utopia.uv.es |
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Abstract: | The pseudo-intramolecular Diels-Alder (DA) reaction between a 2-substituted furan (1) and a N-maleimide derivative (2) has been analyzed using DFT methods. Formation of two hydrogen bonds between the appendages on furan and maleimide derivatives favors thermodynamically the formation of a molecular complex (MC1) through an efficient molecular recognition process. The large enthalpy stabilization associated with the molecular recognition overcomes the unfavorable activation entropy associated with the bimolecular process. As a consequence, the subsequent DA reaction is clearly accelerated through a pseudo-intramolecular process. |
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