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Solvent effect on cycloaddition of C 20 nanofullerene with indoline‐2‐one, at density functional theory
The biologically active ( E )‐3‐(furan‐2‐yl)methylene‐indoline‐2‐one ( I ) is studied, in the gas phase, C 6 H 6 , C 2 H 4 Cl 2 , EtOH, MeNO 2 , DMSO, and H 2 O using the self‐consistent reaction field (SCRF)—density functional theory (DFT). This species has been used in tumor growth, metastasis, an...
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Published in: | Journal of physical organic chemistry 2022-09, Vol.35 (9) |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | The biologically active (
E
)‐3‐(furan‐2‐yl)methylene‐indoline‐2‐one (
I
) is studied, in the gas phase, C
6
H
6
, C
2
H
4
Cl
2
, EtOH, MeNO
2
, DMSO, and H
2
O using the self‐consistent reaction field (SCRF)—density functional theory (DFT). This species has been used in tumor growth, metastasis, and angiogenesis. A mainly interesting issue is the solvent effect on the stability, geometry, and energy of intermolecular hetero‐Diels–Alder cycloaddition of
I
with
C
20
to yield drug delivery (
I
a
). By optimization of adduct (
I
a
) from gas phase to nonpolar and then polar solvent, the following results is obtained: (1) The trend of thermodynamic and kinetic stability and also polarity seem proportional to the dielectric constant of the used solvent and formation of the hydrogen bonding. (2) In contrast to general belief that the
endo
isomer appears more stable than
exo
isomer, here, the
exo
isomer appears more stable than
endo
isomer. (3) The
exo
cycloaddition can be carried out thermally at room temperature and currently hold responsible for regioselectivity. (4) The possibility of
endo
cycloaddition is favorable by the lowest energy barrier of 4.2 kcal/mol probed in benzene, while the highest energy barrier of 7.3 kcal/mol is estimated in water. (5) Nonbonding electrostatic interaction between the sulfur heteroatom and nanocage, as well as the π–π aromatic stacking, appears to have significant destabilizing effect on the
endo
isomer. (6) In going from
exo
transition state (TS) and
endo
TS to and
I
a
cycloadduct, the molecular electrostatic potential is changed as a function of shape, size, symmetry, and regioselectivity. |
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ISSN: | 0894-3230 1099-1395 |
DOI: | 10.1002/poc.4354 |