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Substituent effects on carbon‐13 chemical shifts in 2,6‐disubstituted adamantanes
Author(s) -
Majerski Zdenko,
Vinković Vladimir,
Meić Zlatko
Publication year - 1981
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270170305
Subject(s) - substituent , additive function , chemical shift , chemistry , carbon fibers , medicinal chemistry , stereochemistry , mathematics , mathematical analysis , algorithm , composite number
Carbon‐13 NMR spectral data for a series of symmetrical 2,6‐disubstituted adamantanes (O, CH 2 , CH 3 , OH, OCOCH 3 ) are presented. The substituent effects on 13 C chemical shifts are additive, except for carbons 2 and 6 in 2,6‐adamantanedione. The non‐additivity of the substituent effect in the diketone can be interpreted in terms of a through‐space interaction of the carbonyl π‐electrons; the additivity in the other derivatives indicates that there is no appreciable interaction between the substituents.