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Dynamic NMR Spectroscopy of Three 2,2'-dialkyl/aryl-1-picrylhydrazines in Liquid Solution

Dynamic NMR Spectroscopy of Three 2,2'-dialkyl/aryl-1-picrylhydrazines in Liquid Solution

K C Brown, M El-Bermani, J A Weil

Spectrochim Acta A Mol Biomol Spectrosc. 2010 Jan;75(1):381-8.

PMID: 19944639

Abstract:

We have studied and compared the proton nuclear magnetic resonance spectra of a series of three 2,2'-di(alkyl/aryl)-1-(2,4,6-trinitrophenyl)hydrazines at 500 MHz in liquid toluene-d(8), with a view to learning details of the internal conformation changes taking place, as a function of temperature. Herein "alkyl" denotes 'methyl', and "aryl" denotes 'phenyl'. The synthesis and characterization of 2-phenyl,2'-methyl-1-picrylhydrazine is reported. One goal of the present study was to afford a comparison with the oxidation products, i.e., the three corresponding hydrazyl free radicals - which show striking differences. All the hydrazine molecules in liquid solution occur as interconverting enantiomorphic pairs (atropisomers). Advanced techniques for obtaining the relevant activation energies and pseudo-thermodynamic parameters (Arrhenius and Eyring) have been utilized, and these parameters are listed and discussed. The three hydrazines turn out be very similar with respect to their internal dynamics.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AS212587	Meprobamate-D7 (2-methyl-1,3-propanediol-D7) solution			Price

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