JOURNAL ARTICLE

Captodative Versus Push‐Pull Aromatic Cyclopentadienyl Derivatives.

  • Published In: International Journal of Quantum Chemistry, 2024, v. 124, n. 19. P. 1 1 of 3

  • Database: Academic Search Ultimate 2 of 3

  • Authored By: Shainyan, B. A. 3 of 3

Abstract

The problem of whether and how the captodative aromatic systems with the donor and acceptor substituents at the same carbon atom of the C=C bond can be more stable than the π‐conjugated push‐pull counterparts with the two substituents in the vicinal position is analyzed for cyclopentadienyl derivatives possessing an aromatic cyclopentadienyl ring. The analysis of electronic, magnetic, and structural criteria of aromaticity showed that among typical organic donors, such as amines NR3, ethers R2O, guanidine (NH2)2C=NH, siloxane O(SiH3)2, silatrane, the captodative isomers [cyclopentadienylium]−C(X+) = CH2 can be more stable than their push‐pull isomeric counterparts [cyclopentadienylium]−—CH=CH—X+. The largest energy difference in favor of the former was found to be ca. 13 kcal/mol for X = NH=C(NH2)2. [ABSTRACT FROM AUTHOR]

Additional Information

  • Source:International Journal of Quantum Chemistry. 2024/10, Vol. 124, Issue 19, p1
  • Document Type:Article
  • Subject Area:Chemistry
  • Publication Date:2024
  • ISSN:0020-7608
  • DOI:10.1002/qua.27490
  • Accession Number:180109619
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