Density functional study of noncovalent catalysis of the Diels–Alder reaction by the neutral hydrogen bond donors thiourea and urea

2006 ◽  
Vol 765 (1-3) ◽  
pp. 45-52 ◽  
Author(s):  
Aiping Fu ◽  
Walter Thiel
Keyword(s):  
Hydrogen Bond ◽  
Density Functional ◽  
Neutral Hydrogen ◽  
Alder Reaction ◽  
Diels Alder ◽  
Functional Study ◽  
Density Functional Study ◽  
Diels Alder Reaction ◽  
Hydrogen Bond Donors

Synthesis of 2H-Naphtho[2,3-b]thiopyranoquinones and Density Functional Study for the Diels-Alder Reaction of a Benzothiopyranoquinone

Heterocycles ◽  
2000 ◽  
Vol 53 (3) ◽  
pp. 585 ◽  
Author(s):  
Ricardo A. Tapia ◽  
Miriam C. Garate ◽  
Jaime A. Valderrama ◽  
Fernando Zuloaga ◽  
Paul R. Jenkins ◽  
...  
Keyword(s):  
Density Functional ◽  
Alder Reaction ◽  
Diels Alder ◽  
Functional Study ◽  
Density Functional Study ◽  
Diels Alder Reaction

ChemInform Abstract: Synthesis of 2H-Naphtho[2,3-b]thiopyranoquinones and Density Functional Study for the Diels-Alder Reaction of a Benzothiopyranoquinone.

ChemInform ◽  
2010 ◽  
Vol 31 (26) ◽  
pp. no-no
Author(s):  
Ricardo A. Tapia ◽  
Miriam C. Garate ◽  
Jaime A. Valderrama ◽  
Fernando Zuloaga ◽  
Paul R. Jenkins ◽  
...  
Keyword(s):  
Density Functional ◽  
Alder Reaction ◽  
Diels Alder ◽  
Functional Study ◽  
Density Functional Study ◽  
Diels Alder Reaction

Density functional study of the effect of cation exchanged Sn-Beta zeolite for the diels-alder reaction between furan and methyl acrylate

2020 ◽  
Vol 754 ◽  
pp. 137743
Author(s):  
Veerachart Paluka ◽  
Thana Maihom ◽  
Chompunuch Warakulwit ◽  
Pemikar Srifa ◽  
Bundet Boekfa ◽  
...  
Keyword(s):  
Methyl Acrylate ◽  
Density Functional ◽  
Alder Reaction ◽  
Diels Alder ◽  
Beta Zeolite ◽  
Functional Study ◽  
Density Functional Study ◽  
Diels Alder Reaction

scholarly journals On the Role of Hydrogen Bond Strength and Charge Transfer of a Diels-Alder Reaction On-Water: Semiempirical and Free Energy Calculations.

2021 ◽  
Author(s):  
Andrés Henao Aristizàbal ◽  
Yomna Gohar ◽  
René Whilhelm ◽  
Thomas D. Kühne
Keyword(s):  
Hydrogen Bond ◽  
Free Energy ◽  
Charge Transfer ◽  
Hydrogen Bonds ◽  
Density Functional ◽  
Alder Reaction ◽  
Free Energy Calculations ◽  
Diels Alder ◽  
Diels Alder Reaction

Accelerated chemistry at the interface with water has received increasing attention. The mechanisms behind the enhanced reactivity On-Water are not yet clear. In this work we use a Langevin scheme in the spirit of second generation Car-Parrinello to accelerate the second-order density functional Tight-Binding (DFTB2) method in order to investigate the free energy of two Diels-Alder reaction On-Water: the cycloaddition between cyclopentadiene and ethyl cinnamate or thionocinnamate. The only difference between the reactants is the substitution of a carbonyl oxygen for a thiocarbonyl sulfur, making possible the distinction between them as strong and weak hydrogen-bond acceptors. We find a different mechanism for the reaction during the transition states and uncover the role of hydrogen bonds along with the reaction path. Our results suggest that acceleration of Diels-Alder reactions do not arise from an increased number of hydrogen bonds at the transition state and charge transfer plays a significant role. However, the presence of water and hydrogen-bonds is determinant for the catalysis of these reactions.

scholarly journals On the Role of Hydrogen Bond Strength and Charge Transfer of a Diels-Alder Reaction On-Water: Semiempirical and Free Energy Calculations.

2021 ◽  
Author(s):  
Andrés Henao Aristizàbal ◽  
Yomna Gohar ◽  
René Whilhelm ◽  
Thomas D. Kühne
Keyword(s):  
Hydrogen Bond ◽  
Free Energy ◽  
Charge Transfer ◽  
Hydrogen Bonds ◽  
Density Functional ◽  
Alder Reaction ◽  
Free Energy Calculations ◽  
Diels Alder ◽  
Diels Alder Reaction

Accelerated chemistry at the interface with water has received increasing attention. The mechanisms behind the enhanced reactivity On-Water are not yet clear. In this work we use a Langevin scheme in the spirit of second generation Car-Parrinello to accelerate the second-order density functional Tight-Binding (DFTB2) method in order to investigate the free energy of two Diels-Alder reaction On-Water: the cycloaddition between cyclopentadiene and ethyl cinnamate or thionocinnamate. The only difference between the reactants is the substitution of a carbonyl oxygen for a thiocarbonyl sulfur, making possible the distinction between them as strong and weak hydrogen-bond acceptors. We find a different mechanism for the reaction during the transition states and uncover the role of hydrogen bonds along with the reaction path. Our results suggest that acceleration of Diels-Alder reactions do not arise from an increased number of hydrogen bonds at the transition state and charge transfer plays a significant role. However, the presence of water and hydrogen-bonds is determinant for the catalysis of these reactions.

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