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A proton and carbon NMR spectroscopic study of 5-substituted acenaphthenes

✍ Scribed by Gnanasambandam Vasuki; Subbu Perumal; Veerappan Vijayabaskar; Sangavanaickar Selvaraj; M. Ramalingam; P. Venuvanalingam

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
73 KB
Volume
36
Category
Article
ISSN
0749-1581

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✦ Synopsis

The proton and carbon NMR spectra of eight 5-substituted acenaphthenes were obtained. The 13C chemical shifts of C-6 and C-2a of these compounds were compared with those of carbons located at structurally similar positions in 1-substituted naphthalenes (viz. C-8 and C-4). The 13C chemical shifts of C-2a were also analysed using the dual substituent parameter (DSP) equation. The results revealed (i) diminished steric interactions between the 5-substituent and the adjacent peri-carbon (C-6) and (ii) an enhanced transmission of both polar and resonance e †ects to the carbon para (C-2a) to the variable substituent, X, in acenaphthenes relative to the corresponding carbons (C-4) in 1-substituted naphthalenes. The higher and values observed for C-2a of acenaph-o I o R thenes suggest higher polarizability in this system than in naphthalenes. AM1 calculations of charge also showed enhanced substituent e †ects in the case of most of the substituents in the acenaphthene system.

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