The Diamagnetic Susceptibility of Keto-Enol Tautomers of 2, 4-Pentanedione

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  • NAKAZAWA Yoshinori
    Department of Applied Chemistry, Faculty of Engineering, Utsunomiya University
  • TAKAHASHI Fujio
    Department of Applied Chemistry, Faculty of Engineering, Utsunomiya University

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Other Title
  • 2,4-ペンタンジオンのケト-エノール互変異性体の反磁性磁化率
  • 2 4 ペンタンジオン ノ ケト エノール ゴヘン イセイタイ ノ ハンジセイ

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Description

The diamagnetic susceptibilities of keto and enol tautomers of 2, 4-pentanedione were determined by the Gouy's method. The molar diamagnetic susceptibility of neat 2, 4-pentanedione and mole percent of enol tautomer were found to be -56 x 10-6 cm3 mol-1 and 83%, respectively. The molar diamagnetic susceptibilities of keto and enol tautomers of 2, 4-pentanedione were obtained to be -52.4 x 10-6 and -56.5 x 10-6 cm3 mol-1. While the calculated values of enol tautomer were -53.38 x 10-6 cm3 mol-1by the Pascal-Pacult-Hoarau's way and -53.55 x 10-6 cm3 mol-1 by Harberditzl's way, respectively. The difference between the experimental and the calculated results on enol tautomer was -(3.0 ± 0.7) x 10-6 cm3 mol-1. This could be considered as a result of magnetic anisotropy of enol tautomer of 2, 4pentanedione due to the formation of intramolecular hydrogen bond of six-membered ring, giving a weak ring current effect in the presence of magnetic field.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1998 (1), 19-22, 1998-01-10

    The Chemical Society of Japan

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