4-(3-Azaniumylpropyl)morpholin-4-ium chloride hydrogen oxalate: an unusual example of a dication with different counter-anions

Abstract

, forms an assembly of ionic components which are stabilized through a series of hydrogen bonds and chargeassisted intermolecular interactions. The title assembly crystallizes in the monoclinic C2/c space group with Z = 8. The asymmetric unit consists of a 4-(3-azaniumylpropyl)morpholin-4-ium dication, a hydrogen oxalate counter-anion and an inorganic chloride counter-anion. The organic cations and anions are connected through a network of N-HÁ Á ÁO, O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds, forming several intermolecular rings that can be described by the graph-set notations (9). The 4-(3-azaniumylpropyl)morpholin-4-ium dications are interconnected through N-HÁ Á ÁO hydrogen bonds, forming C(9) chains that run diagonally along the ab face. Furthermore, the hydrogen oxalate anions are interconnected via O-HÁ Á ÁO hydrogen bonds, forming head-to-tail C(5) chains along the crystallographic b axis. The two types of chains are linked through additional N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds, and the hydrogen oxalate chains are sandwiched by the 4-(3-azaniumylpropyl)morpholin-4-ium chains, forming organic layers that are separated by the chloride anions. Finally, the layered three-dimensional structure is stabilized via intermolecular N-HÁ Á ÁCl and C-HÁ Á ÁCl interactions.

Hydrogen-bonding chain and dimer motifs in pyridinium and morpholinium hydrogen oxalate salts

“…whether the O-H bond is cis or trans to the C-C bond. In compound 3, the hydrogen oxalate is the trans conformer and produces a chain along the a-axis direction and is comparable to compounds reported in the Cambridge Structural Database (CSD version 5.39, updated August 2018, Groom et al, 2016, such as ACOQER (Mora et al, 2017) and FOMBIU (Traut-Johnstone et al, 2014). The hydrogen oxalates in compound 2 are in the cis conformation and form a hydrogen-bonded pair, as seen in a small handful of structures: the combination of this pair-wise interaction with a birfurcated hydrogen bond to a pyridinium cation is also seen in EZECOC (Androš et al, 2011;Chen et al 2012,), GULQOV (Thomas et al, 2015;Suresh et al, 2015), LOFMAW (Hu et al, 2014), YEPBAX (Said et al, 2006), YINVUO (Martin et al, 2013) and XEJRIQ (Edwards & Schafer, 2017).…”

Influence of morpholine on changes in kidney tissue and white blood cells of NMRI male Albino mice

“…Oral use of morpholine in mice at the concentration of 2 g/kg of body weight caused nosebleed and gastric bleeding (20). The oral lethal dose of morpholine for mice (LD50) was 525 mg/kg of body weight (7,17). In a study by Van et al, 5 mM of morpholine labeled with carbon-14 by 435 mmol/kg was intravenously injected to 6 groups of male New Zealand rabbits (34).…”

“…Morpholine is used in cosmetics as an additive to hair dye, conditioners, and shampoos (2), and as a disinfectant of water (5). To preserve fruits for a longer time and to process food, morpholine is used in waxes, wrapping coatings, and can be found in device's vapors (6,7). Morpholine is also a good solvent for organic materials such as paints and resins in the paint industry (1,8).…”

“…As a result, liver and lung cancer were reported in mice, liver and kidney cancer in rats, and liver cancer in hamsters (17). In gavage with morpholine palmitate, about 7% of morpholine was excreted in stool (7,17). This substance spreads in all body tissues (18) and has damaging and destructive effects on many tissues.…”