Studies on rotational stability of 2-aryl-3-(2-fluorophenyl)quinazolin-4-one derivatives

Asumi Iida, Kazuya Saito, Nanami Asada, Yuuki Fujimoto, Osamu Kitagawa

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The rotational barriers around an N-(2-F)C6H4 bond in 2-aryl-3-(2-fluorophenyl)quinazolin-4-ones considerably lowered (ca. 4 kcal mol-1 lower) in comparison with those of 2-alkyl-3-(2-fluorophenyl)quinazolin-4-ones. The transition state structure estimated by the DFT calculation indicates that the considerable decrease in the rotational barriers in 2-aryl derivatives is caused by the alleviation of the steric repulsion between an ortho-substituent of 2-fluorophenyl group and 2-aryl group.

Original languageEnglish
JournalHeterocycles
Volume103
Issue number1
DOIs
Publication statusPublished - 2021

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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