Carbon-13 nuclear magnetic resonance examination of naphthalene derivatives. Assignments and analysis of substituent chemical shifts

Abstract

The natural abundance C NMR spectra of a number of substituted naphthalenes have been obtained and assigned by utilization of some or all of the following criteria: (a) specific H incorporation and spectral consequences thereof, (b) fully proton coupled spectra, (c) fluoro substitution, and (d) approximate additivity of substituent effects on chemical shifts for certain dispositions. For crucial sets of 1-and 2-substituted naphthalenes, spectra have been obtained under dilute conditions in chloroform and acetone, and the substituent chemical shifts have been treated by the dual substituent parameter equation (DSP analysis) to provide further insight into the transmission of substituent effects in the naphthyl system.