Protonation of 1,3- and 1,4-dinitrobenzene dianions

Protonation of 1,3- and 1,4-dinitrobenzene dianions Full article

Journal

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

Output data

Year: 2008, Volume: 57, Number: 7, Pages: 1492-1495 Pages count : 4 DOI: 10.1007/s11172-008-0193-6

Authors

Mendkovich A.S. ¹ , Syroeshkin M.A. ¹ , Mikhalchenko L.V. ¹ , Rusakov A.I. ² , Gultyai 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 protonation of the electrochemically generated (0.1 M solution of tetrabutylammonium perchlorate in DMF) 1,3-dinitrobenzene (1) dianions with phenol, ethanol, tert-butanol, and 1-butyl-3-methylimidazolium cation was studied by cyclic voltammetry and chronoamperometry at the carbositall working electrode. The rate constants for the protonation (k) of the dianion of compound 1 by phenol, 1-butyl-3-methylimidazolium cation, ethanol, and tert-butanol were estimated by the comparison of the data of cyclic voltammetry and chronoamperometry with the digital simulation results, being 100, 50, 1.5, and 0.01 L mol−1 s−1, respectively. The similarly obtained k value for the protonation of the dianion of 1,4-dinitrobenzene (2) with phenol is 13 L mol−1 s−1. According to the quantum chemical calculation results, the protonation of the dianions of compounds 1 and 2 with phenol and 1-butyl-3-methylimidazolium cation can be classified as orbital-controlled reactions.

Mendkovich A.S. , Syroeshkin M.A. , Mikhalchenko L.V. , Rusakov A.I. , Gultyai V.P.
Protonation of 1,3- and 1,4-dinitrobenzene dianions
Russian Chemical Bulletin. 2008. V.57. N7. P.1492-1495. DOI: 10.1007/s11172-008-0193-6 WOS Scopus OpenAlex

Web of science:	WOS:000266456700020
Scopus:	2-s2.0-67650480251
OpenAlex:	W2026223758

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