Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
 
Theoretical and Experimental Studies on the Ground- and Excited-State Dipole Moments of 1,4-Naphthoquinone and Its Derivatives
Takehiko SatohMitsutaka KudohTakemasa TsujiShouichi KitaToshiaki MoriSusumu Sudoh
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2007 Volume 80 Issue 6 Pages 1103-1113

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Abstract

The dipole moments of the ground- and excited-states of 1,4-naphthoquinone (1), 2-chloro-1,4-naphthoquinone (2), 2-bromo-1,4-naphthoquinone (3), 2-methyl-1,4-naphthoquinone (4), 2,3-dichloro-1,4-naphthoquinone (5), 2,3-dibromo-1,4-naphthoquinone (6), 2-hydroxy-1,4-naphthoquinone (7), 3-chloro-2-hydroxy-1,4-naphthoquinone (8), 3-bromo-2-hydroxy-1,4-naphthoquinone (9), and 2-hydroxy-3-methyl-1,4-naphthoquinone (10) were studied from both experimental and theoretical perspectives. For the ground states, the dipole moments of compounds 5, 8, and 9 were determined experimentally in dilute solutions (via Debye’s method), and compared with those of the other compounds 14, 6, 7, and 10 which we had already determined. The density functional theory calculations were also performed, revealing a positive correlation with the experimental results. For the excited states, however, the dipole moments of the excited states of compounds 110 have not yet been studied. In this work, we determined the dipole moments of some of the lower excited states of these compounds using the spectroscopic method. Results revealed the determined excited-state dipole moments exceeded those of the ground state, a finding also supported by the configuration interaction involving one-electron excitations only.

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© 2007 The Chemical Society of Japan
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