Kinetics of protonation of the 1,2-dinitrobenzene radical anion and dianion by phenol

Kinetics of protonation of the 1,2-dinitrobenzene radical anion and dianion by phenol Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2009, Volume: 58, Number: 2, Pages: 468-472 Pages count : 5 DOI: 10.1007/s11172-010-0034-2

Authors

Syroeshkin M.A. ¹ , Mendkovich A.S. ¹ , Mikhal’chenko L.V. ¹ , Rusakov A.I. ² , Gul’tyai V.P. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2	P. G. Demidov Yaroslavl State University, 14 ul. Sovetskaya, 150000, Yaroslavl, Russian Federation

The kinetics of protonation of electrochemically generated 1,2-dinitrobenzene (1,2-DNB) radical anions and dianions by phenol in DMF was studied by chronoamperometry. In the presence of phenol, the rate-determining step of electroreduction at the first wave potentials is the protonation of the 1,2-DNB radical anion with a rate constant of 103±13 L mols-1 ss-1. The number of electrons involved in the process with phenol excess is 3, which corresponds to the formation of azoxy compounds. At the second wave potentials under these conditions, the electroreduction process is four-electron, which corresponds to the formation of 2-nitrophenyl-hydroxylamine, The rate constant for 1,2-DNB dianion protonation is 265±60 Lmols-1 ss-1. The comparison of the experimental data with the results of quantum chemical calculation suggests the orbital control of the protonation reaction.

Syroeshkin M.A. , Mendkovich A.S. , Mikhal’chenko L.V. , Rusakov A.I. , Gul’tyai V.P.
Kinetics of protonation of the 1,2-dinitrobenzene radical anion and dianion by phenol
Russian Chemical Bulletin. 2009. V.58. N2. P.468-472. DOI: 10.1007/s11172-010-0034-2 WOS Scopus OpenAlex

Web of science:	WOS:000275907000029
Scopus:	2-s2.0-77950231103
OpenAlex:	W2072674501

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