Synthesis and Study of Mono(arylhydrazino)acenaphthenones and Nickel Complex based on Pyridine-substituted Derivative

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Abstract

Three mono(arylhydrazino)acenaphthenones, that is, mono(2-pyridylhydrazino)acenaphthenone (Py-mhan, L1), mono(4-cyanophenylhydrazino)acenaphthenone (4-CN-Ph-mhan, L2), and mono(3,4,6-trifluoro-2-pyridylhydrazino)acenaphthenone (FPy-mhan, L3), were synthesized by the reaction of acenaphthene quinone with the appropriate arylhydrazine salt; compounds L2 and L3 were obtained for the first time. The subsequent reaction of L1 with nickel chloride in 2 : 1 ratio led to the octahedral complex [Ni(Py-mhan)2] (I), in which Py-mhan acts as a tridentate ligand. All of the prepared compounds were characterized by elemental analysis, IR and 1H NMR spectroscopy, and cyclic voltammetry; the crystal structures of L3 and I were determined by X-ray diffraction.

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About the authors

I. V. Bakaev

Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences

Email: nikolaj.romashev75@gmail.com
Russian Federation, Novosibirsk

V. I. Komlyagina

Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences; Novosibirsk State National Research University

Email: nikolaj.romashev75@gmail.com
Russian Federation, Novosibirsk; Novosibirsk

N. F. Romashev

Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences

Author for correspondence.
Email: nikolaj.romashev75@gmail.com
Russian Federation, Novosibirsk

A. L. Gushchin

Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences

Email: nikolaj.romashev75@gmail.com
Russian Federation, Novosibirsk

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Supplementary files

Supplementary Files
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1. JATS XML
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2. Scheme 1. Synthesis of compounds L1-L3, I and numbering of protons in compounds L1-L3

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3. Fig. 1. Molecular structure of L3 according to PCA data

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4. Fig. 2. Molecular structure of I according to PCA data

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5. Fig. 3. CBA curves of the L1-L3 compounds in the potential range from -1.6 to 1.7 V (for L1); -1.75 to 1.8 V (for L2); -1.5 to 2.0 V (for L3) (CH2Cl2, SU electrode, c(L1-L3) = 8 × 10-4-2 × 10-3 M, v = 100 mV/s, 0.1 M nBu4NPF6, rt. Ag/AgCl))

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6. Scheme 2. Ar-mhan redox processes

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7. Fig. 4. CVA curves of compound I in the potential range from 0 to -1.7 V and 0 to 2.0 V (CH2Cl2, SU electrode, c(L1-L3) = 1 × 10-3 mol/L, v = 100 mV/s, 0.1 mol/L nBu4NPF6, rt. Ag/AgCl))

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