ISSN:
0749-1581
Keywords:
1H, 13C, 17O NMR spectra
;
Disubstituted naphthalenes
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 1H, 13C and 17O NMR spectra of several 4,1-disubstituted naphthalenes, viz. 4-substituted 1- acetylnaphthalenes (series 1), 4-substituted 1-nitronaphthalenes (series 2), 4-substituted 1-methoxynaphthalenes (series 3) and 4-substituted 1-naphthyl methyl sulphides (series 4), were measured. The 17O and 13C chemical shifts of these 4,1-disubstituted naphthalenes were compared with those of the corresponding 4,1-disubstituted benzenes and analysed using the dual substituted parameter (DSP) equation. It is concluded that in series 1, 2 and 4 the substituent effects from the 4-substituent to the C-1 carbon and the side-chain atoms are transmitted more effectively than those in the corresponding 4,1-disubstituted benzenes, whereas the transmission in series 3 is almost equal to that in the analogous benzene series, viz. 4-substituted anisoles. The reverse substituent effects displayed by the H-8 chemical shifts of series 1 and 2 and the existence of linear relationships between the chemical shifts of H-8 and the 17O chemical shifts of the oxygen of both the acetyl and nitro groups in series 1 and 2, respectively, are ascribed mainly to changes in the electron densities on the oxygen of the carbonyl and nitro groups affecting the diamagnetic screening of the proton.
Additional Material:
12 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260300409
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