Thermodynamic selectivity of multicenter chemical reactions. A statistical quantification of a widespread intuitive approach and its application to reactions of fullerenes

Sabirov, Denis Sh.; Shepelevich, Igor S.; Tumanskii, B. L.

doi:10.1016/j.comptc.2018.06.002

Cited by 7 publications

(2 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Note that the higher reactivity of the cis-1 bond in C 60 X is the experimentally known fact con rmed for various non-bulky X (so that the addition of the X groups to the fullerene core meet no steric hindrances) (cf. [4,12,17,18,24,25,27]).…”

Section: Resultsmentioning

confidence: 99%

“…Upon decorating the C 60 cage with chemical groups, it loses the original symmetry. As consequence, the reaction sites of cycloaddition (chemical bonds) become inequivalent and the number of regioisomers corresponding to C 60 X n increases with n [16][17][18]. It makes both experimental and theoretical chemistry of fullerene multiadducts complicated.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Bader’s bond ellipticity as a reactivity index for stepwise [2+1]-cycloaddition to the C60 fullerene

Tukhbatullina,

Shepelevich,

Sabirov

2023

Preprint

Self Cite

View full text Add to dashboard Cite

Selectivity of chemical reactions of fullerenes is a challenge of fullerene science, as there is no universal tool to predict the favorability of the alternative reaction modes within one reactivity index. In the present work, using Bader’s theory Atoms-in-Molecules, we have studied the ellipticities of the C = C bonds in the molecules of fullerene adducts C60Xn (n = 1–3) with symmetric addends X = CH2 and O. We have obtained the correlations between the thermodynamic stability of the fullerene adducts and bond ellipticities in the molecular of their precursors. The found regularity may be further used for predicting the reactivity of fullerene derivatives and estimating of regioselectivity of the cycloaddition reactions.

show abstract