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‘Lone Pair’ and ‘CI Bond’ Ionization Energies of exo ‐ and endo ‐2‐Norbornyl Iodides
Author(s) -
Honegger Evi,
Heilbronner Edgar,
Dratva Alfred,
Grob Cyril A.
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670704
Subject(s) - 2 norbornyl cation , chemistry , substituent , lone pair , group (periodic table) , stereochemistry , ionization energy , crystallography , ionization , organic chemistry , molecule , ion
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 ‐CX bond is better stabilized by the 2‐norbornyl group than a semi‐localized, positive hole in an endo ‐CX bond.