Effect of binding pockets on the kinetics and thermodynamics of Diels-alder reaction in cucurbit-Uril family.
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| Title: | Effect of binding pockets on the kinetics and thermodynamics of Diels-alder reaction in cucurbit-Uril family. |
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| Authors: | Ayub, Amna1 (AUTHOR), Hashmi, Muhammad Ali1,2 (AUTHOR) muhammad.hashmi@ue.edu.pk, Bhatti, Haq Nawaz1 (AUTHOR), Jamil, Yasir3 (AUTHOR), Iqbal, Javed1,4 (AUTHOR) Javed.Iqbal@uaf.edu.pk |
| Source: | Journal of Molecular Structure. Jan2024:Part 2, Vol. 1296, pN.PAG-N.PAG. 1p. |
| Subjects: | Thermodynamics, Exothermic reactions, Molecular size, Tetracyanoethylene, Families, Diels-Alder reaction |
| Abstract: | • Studied the influence of encapsulation on the kinetics and thermodynamics of the Diels-Alder reaction. • Effects of binding pockets on the Diels-Alder reaction are explored by selecting CB n(n = 5–8) -uril. • CB6-uril has the lowest activation energy of ≈ 19.45 kcal mol−1, predicting CBn-uril as an effective cavity for researching the Diels-Alder process. Cucurbit-uril (CB-uril) family has witnessed a considerable increase in popularity over the last two decades due to its amazing binding ability which impart broad range of applications. Cucurbit-uril family members exhibit diversity in their binding pocket to accommodate guest molecules of different sizes which in turn impact the remarkable properties of these molecules. Herein, we have studied the influence of encapsulation on the kinetics and thermodynamics of the Diels-Alder reaction. Effects of binding pockets on the Diels-Alder reaction are explored by selecting CB n(n = 5–8) -uril. Bond evolution theory (BET) and non-covalent interaction (NCI) analyses have also been performed to gain insight into electronic distribution along the reaction route as well as bond formation/breakage to understand the mechanism of action and the role of weak/strong interactions between CBn-uril and reaction during the process. Activation energies for Diels-Alder reaction in CB n=6–8 -uril (22.63 kcal mol−1, 21.37 kcal mol−1, and 19.45 kcal mol−1, respectively) are significantly lower than that of the bare reaction (25.45 kcal mol−1). While for P-DA reactions, activation energies within CB n=7,8 -uril are observed as 19.29 kcalmol−1 and 14.45 kcalmol−1 (cis-1,2-dicyanoethylene), 18.46 kcalmol−1 and 14.65 kcalmol−1 (trans-1,2-dicyanoethylene), and 16.01 kcalmol−1 and 20.86 kcalmol−1 (tetracyanoethylene). CB7-uril has predicted the lowest activation energies for DA reaction with cis-1,2-dicyanoethylene and trans-1,2-dicyanoethylene compared to bare E a ≈ 20.15 kcalmol−1 and 19.57 kcalmol−1, respectively. By making the reaction more exothermic with E R ≈ -40 kcal mol−1, CB6-uril has the lowest activation energy of ≈ 19.45 kcal mol−1, predicting CBn-uril as an effective cavity for researching the Diels-Alder process. [Display omitted] [ABSTRACT FROM AUTHOR] |
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| Database: | Engineering Source |
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