‘Lone Pair’ and ‘CI Bond’ Ionization Energies of exo- and endo-2-Norbornyl Iodides

✍ Scribed by Evi Honegger; Edgar Heilbronner; Alfred Dratva; Cyril A. Grob

• Book ID: 102254080
• Publisher: John Wiley and Sons
• Year: 1984
• Tongue: German
• Weight: 427 KB
• Volume: 67
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19840670704

✦ Synopsis

Abstract

A PE‐spectroscopic study of exo‐ and endo‐2‐norbornyl iodides suggests that the relative ability of the 2‐norbornyl group to stabilize an electron deficiency on a substituent X (e.g. I) in exo‐ or endo‐position depends on the location of the positive charge. There is no difference if the positive hole is strongly localized on on the substituent X (e.g. the 5p^−1^ state of the title compounds). On the other hand, our results indicate that teh positive hole semi‐localized in an exo‐CX bond is better stabilized by the 2‐norbornyl group than a semi‐localized, positive hole in an endo‐CX bond.