Mechanistic aspects of the synthesis of seven-membered internal nitronates via stepwise [4 + 3] cycloaddition involving conjugated nitroalkenes: Molecular Electron Density Theory computational study.
J Comput Chem
; 43(18): 1221-1228, 2022 Jul 05.
Article
in En
| MEDLINE
| ID: mdl-35535613
ABSTRACT
The density functional theory computational study indicates the possibility of the synthesis of seven-membered internal nitronates via cycloaddition reactions involving Z-C-aryl-N-methylnitrones and E-2-aryl-1-cyano-1-nitroethenes. The detailed exploration of the reaction paths indicates a polar, stepwise reaction mechanism through the zwitterionic intermediate. Using bonding evolution theory (BET), we have deciphered the molecular mechanism of the [4 + 3] cycloaddition reaction between E-2-phenyl-1-cyano-1-nitroethene and Z-C-phenyl-N-methylnitrone. The BET study has revealed that the formation of two CO single bonds takes place in the same way, through the depopulation of NC and CC bonding regions and monosynaptic basins, respectively. The first O1C7 single bond was formed in the sixth phase, while the second C3O4 bond was formed in the last ninth phase.
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Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Comput Chem
Year:
2022
Document type:
Article