Crystal structure and Hirshfeld surface analysis of 1,2-ethylene-bis (para-methyl pyridinium) dichromate as a new selective and mild agent in oxidation of alcohols

Authors

MOSTAFA GHOLIZADEH
MEHRDAD POURAYOUBI
MOHAMMAD REZA HOUSSIENDOKHT
HADI AMIRI RUDBARI
MASOUMEH FARIMANEH
ANAHID SANEEI
GIUSEPPE BRUNO

Abstract

1,2-Ethylene-bis(para-methyl pyridinium) dichromate, (C$_{14}$H$_{18}$N$_{2})$[Cr$_{2}$O$_{7}$], is used as a new oxidizing agent in conversion of some alcohols to their corresponding carbonyl compounds in CH$_{3}$CN solvent and also under solvent-free conditions. In both procedures, high conversion percentages are observed. However, a much shorter reaction time is achieved in solvent-free conditions. For allylic alcohols, the C=C bond is not oxidized and the examined saturated alcohol in this work (i.e. cyclo-hexanol) remains intact, which illustrates the mild nature of reagent used. The structure of the reagent is investigated by single-crystal X-ray diffraction analysis. The C--H$\cdots$O and O$\cdots \pi$ interactions are the most important features of crystal packing, which are visualized by the Hirshfeld surface map.

DOI

10.3906/kim-1806-32

Keywords

Alcohol oxidation, 1, 2-ethylene-bis(para-methyl pyridinium) dichromate, Hirshfeld surface analysis, solvent-free condition, X-ray crystallography

First Page

185

Last Page

196

Recommended Citation

GHOLIZADEH, MOSTAFA; POURAYOUBI, MEHRDAD; HOUSSIENDOKHT, MOHAMMAD REZA; RUDBARI, HADI AMIRI; FARIMANEH, MASOUMEH; SANEEI, ANAHID; and BRUNO, GIUSEPPE (2019) "Crystal structure and Hirshfeld surface analysis of 1,2-ethylene-bis (para-methyl pyridinium) dichromate as a new selective and mild agent in oxidation of alcohols," Turkish Journal of Chemistry: Vol. 43: No. 1, Article 16. https://doi.org/10.3906/kim-1806-32
Available at: https://journals.tubitak.gov.tr/chem/vol43/iss1/16