Repository logo

Infoscience

  • English
  • French
Log In
Logo EPFL, École polytechnique fédérale de Lausanne

Infoscience

  • English
  • French
Log In
  1. Home
  2. Academic and Research Output
  3. Journal articles
  4. The biphenyl-monitored effective size of unsaturated functional or fluorinated ortho substituents
 
research article

The biphenyl-monitored effective size of unsaturated functional or fluorinated ortho substituents

Ruzziconi, Renzo
•
Spizzichino, Sara
•
Mazzanti, Andrea
Show more
2010
Organic & Biomolecular Chemistry

The size of a series of typical substituents has been probed by dynamic NMR measurements of the barriers to aryl-aryl rotation of the corresponding biphenyls. The resulting B values are meaningful because only mono-ortho substituted compounds were investigated and thus the results are not compromised by the non-additivity of multiple steric effects. On the basis of the chosen model system ethynyl and cyano groups were found to be slightly smaller than a phenyl ring. In contrast, vinyl and, in particular, formyl groups proved to be larger than phenyl. The latter difference is due to the loss of conjugation forces at the planar transition state. alpha-Hydroxyhexafluoroisopropyl is slightly more bulky than tert-butyl. Pentafluorophenyl and trifluoromethoxy exhibit nearly the same effective size as phenyl and methoxy, respectively Trifluoromethyl is somewhat smaller than isopropyl.

  • Files
  • Details
  • Metrics
Loading...
Thumbnail Image
Name

c0ob00136h.pdf

Type

Publisher's Version

Version

Published version

Access type

openaccess

Size

261.53 KB

Format

Adobe PDF

Checksum (MD5)

7c21a35a9b588dfd5a72631f0c728882

Logo EPFL, École polytechnique fédérale de Lausanne
  • Contact
  • infoscience@epfl.ch

  • Follow us on Facebook
  • Follow us on Instagram
  • Follow us on LinkedIn
  • Follow us on X
  • Follow us on Youtube
AccessibilityLegal noticePrivacy policyCookie settingsEnd User AgreementGet helpFeedback

Infoscience is a service managed and provided by the Library and IT Services of EPFL. © EPFL, tous droits réservés