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

Jadwiga Lorenc , Jerzy Hanuza , J. Janczak

Abstract

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,,
-
, J. Janczak
J. Janczak,,
-
Journal seriesVibrational Spectroscopy, ISSN 0924-2031, (A 25 pkt)
Issue year2012
Vol59
Pages59-70
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
DOIDOI:10.1016/j.vibspec.2012.01.003
Languageen angielski
Score (nominal)25
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)
Cite
Share Share

Get link to the record


* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
Back