Ab initio modeling of the solvent influence on the azo-hydrazone tautomerism

被引：54
|
作者：
Antonov, L
Kawauchi, S
Satoh, M
Komiyama, J
机构：
[1] Natl Foresty Univ, Dept Ecol, Sofia 1756, Bulgaria
[2] Tokyo Inst Technol, Dept Polymer Sci, Meguro Ku, Tokyo 152, Japan
来源：
DYES AND PIGMENTS | 1999年 / 40卷 / 2-3期
关键词：
tautomerism; azo dyes; hydrogen bonding; solvent effect;
D O I：
10.1016/S0143-7208(98)00044-8
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The solvent effect on the azo (A) -hydrazone (H) tautomeric equilibrium of 1-phenylazo-4-naphthol is modeled by using ab initio quantum-chemical calculations. It was found that in methanol, methylene chloride and water there exists a strong hydrogen bonding between the particular tautomer and solvent, as well as dipole-dipole dye-solvent interactions. The results show that the H-form is more stable in water and methylene chloride, while methanol and i-octane stabilize the A-form. The calculational results obtained are in very good agreement with the experimental data in these solvents published previously. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：163 / 170
页数：8
相关论文
共 50 条
  • [41] Azo-hydrazone tautomerism in a simple coumarin azo dye and its contribution to the naked-eye detection of Cu2+and other potential applications
    Ngororabanga, Jean Marie Vianney
    Dembaremba, Tendai O.
    Mama, Neliswa
    Tshentu, Zenixole R.
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2023, 289
  • [42] EFFECT OF AZO-HYDRAZONE TAUTOMERIZATION ON SOLID STATE AGGREGATION OF ARYLAZONAPHTHOLS
    MONAHAN, AR
    DELUCA, AF
    WARD, AT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1971, (NSEP): : 24 - &
  • [43] The syntheses, structures and azo-hydrazone tautomeric studies of three triazole/tetrazole azo dyes
    Cai, Jiawei
    Li, Zhixin
    Qiu, Yanxuan
    OuYang, Zhijian
    Lin, Wenning
    Yang, Liu
    Feng, Weijin
    Yu, Xinwei
    Dong, Wen
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (11) : 9370 - 9379
  • [44] AZO-HYDRAZONE CONVERSION .1. JAPP-KLINGEMANN REACTION
    YAO, HC
    RESNICK, P
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (18) : 3514 - &
  • [45] Novel colorimetric sensors for cyanide based on azo-hydrazone tautomeric skeletons
    Adegoke, Olajire A.
    Adesuji, Temitope E.
    Thomas, Olusegun E.
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 128 : 147 - 152
  • [46] Impact of amino acids, organic solvents and surfactants on azo-hydrazone tautomerism in Methyl Red: spectral-luminescent and nonlinear optical properties
    Sharifi, Soheil
    Nazar, Muhammad Faizan
    Rakhshanizadeh, Forough
    Sangsefedi, Seyed Ahmad
    Azarpour, Afshin
    OPTICAL AND QUANTUM ELECTRONICS, 2020, 52 (02)
  • [47] Comparative studies of excited state intramolecular proton transfer (ESIPT) and azo-hydrazone tautomerism in naphthalene-based fluorescent acid azo dyes by computational study
    Shinde, Suvidha
    Sekar, Nagaiyan
    PHYSICAL SCIENCES REVIEWS, 2022, 7 (08) : 811 - 831
  • [48] Reactivity of phenylazonaphthol sulfonates, their estimation by semiempirical molecular orbital PM5 method, and the relation between their reactivity and azo-hydrazone tautomerism
    Hihara, T
    Okada, Y
    Morita, Z
    DYES AND PIGMENTS, 2003, 59 (03) : 201 - 222
  • [49] Impact of amino acids, organic solvents and surfactants on azo-hydrazone tautomerism in Methyl Red: spectral-luminescent and nonlinear optical properties
    Soheil Sharifi
    Muhammad Faizan Nazar
    Forough Rakhshanizadeh
    Seyed Ahmad Sangsefedi
    Afshin Azarpour
    Optical and Quantum Electronics, 2020, 52
  • [50] Effect of dye aggregation and azo-hydrazone tautomerism on the photocatalytic degradation of Solophenyl red 3BL azo dye using aqueous TiO2 suspension
    Habibi, MH
    Hassanzadeh, A
    Zeini-Isfahani, A
    DYES AND PIGMENTS, 2006, 69 (03) : 111 - 117
12345