Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Computational insight of the mechanism of Algar-Flynn-Oyamada (AFO) reaction
Synthetic Chemistry Division, Defense R and D Establishment.
Department of Chemistry, Bengal Engineering and Science University.
Number of Authors: 2
2014 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 4, no 36, 18702-18709 p.Article in journal (Refereed) Published
Abstract [en]

The present DFT investigation supports a previous conclusion of Dean et al. that hydroxylation occurs without epoxide intermediate at room temperature due to a strong electrostatic interaction of peroxide ions with π electrons of CC bonds of chalcone, and 3-hydroxyflavone has been found to be the major product. The calculated activation energy difference (ΔG#) of initial enolization followed by hydroxylation or simultaneous cyclization and hydroxylation has been found to be negligible (∼4 kcal mol-1). On the other hand, epoxide formation requires significant activation energy, which is supposed to occur at high temperatures. In addition, if epoxide is formed, the ring opens by an attack of phenolic oxygen, occurring preferentially at α position via a five-member transition state due to a low activation barrier height (19.82 kcal mol-1 in the gas phase and 19.55 kcal mol-1 in ethanol) compared to that of a six-member transition state (44.41 kcal mol-1 at B3LYP in the gas phase and 38.55 kcal mol -1 in ethanol). It is also observed that the solvation study does not affect the main conclusion of the paper. These findings also support the previous observation of Dean et al. Predicted ΔG# in different DFT functionals are consistent, although the total energy is significantly different

Place, publisher, year, edition, pages
2014. Vol. 4, no 36, 18702-18709 p.
National Category
Physical Chemistry
Research subject
Chemistry of Interfaces
Identifiers
URN: urn:nbn:se:ltu:diva-62728DOI: 10.1039/c3ra46623jOAI: oai:DiVA.org:ltu-62728DiVA: diva2:1085100
Available from: 2017-03-28 Created: 2017-03-28 Last updated: 2017-03-28Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Bhattacharyya, Shubhankar
In the same journal
RSC Advances
Physical Chemistry

Search outside of DiVA

GoogleGoogle Scholar

Altmetric score

CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf