Structural and vibrational study of 3- or 5-methyl substituted 2-N-ethylamino-4-nitropyridine N-oxides

Jadwiga Lorenc , Jerzy Hanuza , Jan Janczak


X-ray crystal structures of two isomers C8H11N3O3, i.e. 2-N-ethylamino-5-methyl-4-nitropyridine N-oxide (EN5MPO) and 2-N-ethylamino-3-methyl-4-nitropyridine N-oxide (EN3MPO) have been determined. The different substitutions of the single bondCH3 groups lead to change of the unit-cell structure, molecular and intermolecular arrangement. Both structures are monoclinic, space group P21/c and P21/n with a parallel and antiparallel orientation along the a-axis, respectively. In each of the two subunits, the methyl carbons and N-atoms of the nitro group are almost coplanar with the pyridine ring, but the N-oxide bonds are inclined from this plane. The crystal structures are stabilized by a set of the weak inter- and intramolecular hydrogen bonds of the Nsingle bondH⋯O type. The structures of both isomers have been confirmed by the results of IR and Raman spectra measurements, quantum chemical calculations and potential energy distribution (PED). The role of methyl group introduced in 3 or 5 position of 2-N-ethylamino-4-nitropyridine N-oxide has been analysed.
Author Jadwiga Lorenc (EaE / IChaFT / DBCh)
Jadwiga Lorenc,,
- Department of Bioorganic Chemistry
, Jerzy Hanuza
Jerzy Hanuza,,
, Jan Janczak - Institute of Low Temperatures and Structure Research Polish Academy of Sciences (INTiBS PAN) [Polish Academy of Sciences (PAN)]
Jan Janczak,,
Journal seriesVibrational Spectroscopy, ISSN 0924-2031, (A 25 pkt)
Issue year2012
Keywords in English2-N-ethylamino-3-methyl-4-nitropyridine N-oxide, 2-N-ethylamino-5-methyl-4-nitropyridine N-oxide, Crystal structure, Hydrogen bonds, Vibrational properties, DFT calculations
ASJC Classification1607 Spectroscopy
Languageen angielski
Score (nominal)25
Score sourcejournalList
Publication indicators Scopus SNIP (Source Normalised Impact per Paper): 2014 = 1.244; WoS Impact Factor: 2012 = 1.747 (2) - 2012=1.978 (5)
Citation count*6 (2016-07-26)
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