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Anomalous Appearance of ν[C(2)=C(3)] Frequencies in IR Spectra of 1,4-Naphthoquinone Hydroxy Derivatives

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Journal of Applied Spectroscopy Aims and scope

Absorption bands in the carbonyl range 1750–1500 cm–1 of the IR spectrum of 2,3-dihydroxy-1,4-naphthoquinone and some of its derivatives were assigned based on calculations of normal mode frequencies using the B3LYP/cc-pVTZ method for isolated molecules and the polarized continuum model taking into account the influence of weakly and moderately polar solvents (CCl4, CDCl3, and CH2Cl2). It was shown that the frequency of the quinone C(2)=C(3) stretching vibration for 2,3-OH- and 2,5,8-OH-1,4-naphthoquinones (2-OH-naphthazarins) was 50–60 cm–1 higher than that of the carbonyl stretching vibration. The frequency difference reached 100 cm–1 for 2,3,5,8-OH-1,4-naphthoquinones (2,3-OH-naphthazarins).

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Authors and Affiliations

  1. G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch, Russian Academy of Sciences, 159 100-Let Vladivostoku Ave., Vladivostok, 690022, Russia

    V. P. Glazunov & D. V. Berdyshev

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  1. V. P. Glazunov
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  2. D. V. Berdyshev
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Correspondence to V. P. Glazunov.

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Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 81, No. 4, pp. 499–509, July–August, 2014.

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Glazunov, V.P., Berdyshev, D.V. Anomalous Appearance of ν[C(2)=C(3)] Frequencies in IR Spectra of 1,4-Naphthoquinone Hydroxy Derivatives. J Appl Spectrosc 81, 553–564 (2014). https://doi.org/10.1007/s10812-014-9969-7

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