ISSN 0036-0236, Russian Journal of Inorganic Chemistry, 2014, Vol. 59, No. 6, pp. 541–544. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © R.E. Khoma, V.O. Gelmboldt, O.V. Shishkin, V.N. Baumer, A.N. Puzan, A.A. Ennan, I.M. Rakipov, 2014, published in Zhurnal Neorganicheskoi Khimii,
2014, Vol. 59, No. 6, pp. 716–719.
541
N-(2-hydroxyethyl)ethylenediamine (HEEDA)
and its derivatives are used as fuel additives [1], chelat-
ing agents [2], epoxy hardeners, emulsifiers, deter-
gents, corrosion inhibitors [3], surfactants [4], and
comonomers in the production of polyester materials
contacting with food, enzymes, and flavorings [5]. In
reactions with acids, HEEDA can be protonated at
both primary and secondary amino groups; and ace-
tate and formate salts of HEEDA manifest the proper-
ties of ionic liquids [6].
Ethanolammonium onium sulfites and hydro-
sulfites of unctuous consistency have been synthesized
and spectrally characterized by us earlier [7, 8]. The
fact that the structurally studied organic sulfites are
exhausted by tetramethylguanidinium hydrosulfite [9]
and aminoguanidinium sulfite monohydrate [10]
seems to be due to the ease for the sulfites to convert
into sulfates as a result of “autooxidation” [11, 12].
In this work, we have studied the structure and
spectral characteristics of N-(2-hydroxyethyl)eth-
ylenediammonium sulfite monohydrate
(HOCH
2
CH
2
NH
2
CH
2
CH
2
NH
3
)SO
3
⋅ H
2
O (I), the
new onium sulfite produced in a reaction between sul-
fur(IV) oxide and aqueous HEEDA.
EXPERIMENTAL
Synthesis of compound I. A solution of
N-(hydroxymethyl)ethylenediamine (0.05 mol) in
water (20 mL) was poured into a temperature-con-
trolled cell, and gaseous SO
2
was passed through it at
0°С at a rate of 50 mL/min until pH < 1.0 was attained.
The solution was allowed to stand at a temperature
<15°С in air until water vaporized. The separated color-
less crystalline product I (10.04 g; yield, 98.3%) was not
subjected to any additional purification.
Nitrogen, carbon, and hydrogen were determined
on a CHN elemental analyzer; sulfur was determined
by the Schôniger method [13].
For C
4
H
16
N
2
O
5
S, anal. calcd. (%): C, 23.52; N,
13.72; S, 15.70; H, 7.90.
Found (%): C, 22.81; N, 13.34; S, 16.41; H, 8.09.
IR spectra were recorded on a PerkinElmer Spec-
trum BX II FT-IR System spectrometer (range:
4000–350 cm
–1
; KBr pellets).
Electron-impact (EI) mass spectra were taken on
an MX-1321 mass spectrometer (direct injection;
energy of ionizing electrons: 70 eV).
Fast atom bombardment (FAB) mass spectra were
taken on a VG 7070 mass spectrometer (ions were des-
orbed from a liquid matrix using a beam of argon
atoms with an energy of 8 keV).
EI mass spectrum of m/z = 87, I = 6%; m/z = 75,
I = 11%; [M
HEEDA
–CH
2
OH + H]
+
(m/z = 74, I =
56%); m/z = 65, I = 6%; [SO
2
]
+
(m/z = 64, I = 14%);
m/z = 57, I = 41%; m/z = 56, I = 24%; m/z = 45, I =
52%; m/z = 46, I = 9%; m/z = 43, I = 10%; m/z = 34,
I = 12%; m/z = 32, I = 100%; m/z = 30, I = 92%. The
characteristics of HEEDA fragmentation products in
Synthesis and Structure of N-(Hydroxyethyl)ethylenediammonium
Sulfite Monohydrate
R. E. Khoma
a, b
, V. O. Gelmboldt
c
, O. V. Shishkin
d, e
, V. N. Baumer
d, e
,
A. N. Puzan
d
, A. A. Ennan
a
, and I. M. Rakipov
f
a
Physicochemical Institute for Human and Environment Protection, Ministry of Education and Science of Ukraine,
National Academy of Sciences of Ukraine, ul. Preobrazhenskaya 3, Odessa, 65026 Ukraine
b
Mechnikov National University, ul. Dvoryanskaya 2, Odessa, 65025 Ukraine
c
Odessa National Medical University, per. Valikhovskiy 2, Odessa, 65026 Ukraine
d
Institute for Single Crystals, National Academy of Sciences of Ukraine, pr. Lenina 60, Kharkiv, 61178 Ukraine
e
Kharkiv National University, pl. Svobody 4, Kharkiv, 61077 Ukraine
f
Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine,
Lustdorfskaya doroga 86, Odessa, 65080 Ukraine
e-mail: rek@onu.edu.ua, r_khoma@farlep.net
Received December 2, 2013
Abstract—A reaction between sulfur(IV) oxide and aqueous N-(2-hydroxyethyl)ethylenediamine yields
onium sulfite of composition (HOCH
2
CH
2
NH
2
CH
2
CH
2
NH
3
)SO
3
⋅ H
2
O, which has been characterized by
X-ray diffraction, IR spectroscopy, and mass spectrometry. The three-dimensional structure of the salt is sta-
bilized by numerous hydrogen bonds, such as NH⋅⋅⋅O and OH⋅⋅⋅O.
DOI: 10.1134/S0036023614060096
COORDINATION COMPOUNDS