Crystal structures of two solvates of (18-crown-6)potassium acetate

Liebing, Phil; Zaeni, Ahmad; Olbrich, Falk; Edelmann, Frank T.

doi:10.1107/s2056989016017436

Cited by 11 publications

(15 citation statements)

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“…In the title compound, three of the four K-O(carboxylate) contacts are in a range 2.676 (2)-2.802 (2) Å , which is consistent with the values observed in other potassium carboxylates (e.g. Ilczyszyn et al, 2009;Liebing et al, 2016). However, one contact (K1 0 -O1) is strongly elongated to 3.358 (2) Å .…”

Section: Structural Commentarysupporting

confidence: 85%

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Crystal structure of dipotassiumN-carbodithioato-L-prolinate trihydrate

Liebing

2017

Acta Cryst E

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The molecular and crystal structure of the l-proline-derived dithiocarbamatecarboxylate compound poly[tri--aqua-( -2-carboxylatopyrrolidine-1-carbodithioato)dipotassium], [K 2 (C 6 H 7 NO 2 S 2 )(H 2 O) 3 ] n or K 2 (SSC-NC 4 H 7 -COO)Á3H 2 O, has been determined. The dithiocarbamate moiety displays a unique coordination mode, comprising a 'side-on' -coordinated K + cation besides a commonly -chelated K + cation. By bridging coordination of the CSS group, COO group and water molecules, the K + cations are linked into a two-dimensional coordination polymer extending parallel to the ab plane. These layers are again interconnected by O-HÁ Á ÁS hydrogen bonds. Chemical contextNatural amino acids react readily with carbon disulfide in an alkaline environment to give dithiocarbamate-functionalized carboxylates. Since the first report on a series of barium salts in the 1950s (Zahradnik, 1956), numerous transition metal complexes have been explored. More recently, various late transition metal complexes of this family have been investigated due to their biological activity (e.g. Giovagnini et al., 2005;Cachapa et al., 2006;Nagy et al., 2012). In most cases, the dithiocarbamate moiety acts as a classical small-bite chelate ligand, while the carboxylate group (often esterified) does not contribute to metal coordination. The structural chemistry of main group derivatives of dithiocarbamate-derived amino acids is much less explored, even though alkali metal and alkaline earth metal salts are frequently used as precursors for other metal complexes. A key intermediate in our ongoing reasearch on coordination polymers with dithiocarbamatecarboxylates is the l-proline-derived potassium salt K 2 (SSC-NC 4 H 7 -COO). This compound crystallizes from aqueous solution as a trihydrate, which has been structurally characterized in the course of this work. Structural commentaryThe title compound, K 2 (SSC-NC 4 H 7 -COO)Á3H 2 O, crystallized as colourless plates in the orthorhombic space group ISSN 2056-9890 P2 1 2 1 2 1 , with one formula moiety in the asymmetric unit ( Fig. 1). One K atom (K2) is bonded in a typical chelating fashion by the CSS group, while K1 is coordinated 'side-on' to the CSS group, certainly under participation of the delocalized electrons. This rather uncommon coordination mode might be supported by additional coordination of a carboxylate O atom (O1) to K1. K1 adopts a low-symmetric seven-coordination by four carboxylate O atoms, two H 2 O molecules and the -coordinating CSS group. K2 is eight-coordinated by three S atoms and five H 2 O molecules (Fig. 2). Consequently, the full coordination mode of the carboxylate group is 3 -4 O,O 0 :O:O 0 , and the dithiocarbamate group adopts a 3 -6 S,S 0 ,C:S,S 0 :S coordination. One H 2 O molecule displays a 3 -coordination (O3) and the remaining two H 2 O molecules are coordinating in a -bridging mode (O4 and O5). The K-S distances at the -chelated K + cation (K2) are 3.2176 (8) and 3.2650 (9) Å , while the K-S separations at the -coordinated K + cation (K1) are signif...

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Section: Structural Commentarysupporting

confidence: 85%

“…For other potassium carboxylates, see e.g. CONWOS (Ilczyszyn et al, 2009), and BIFMIN01 and BIFMUZ01 (Liebing et al, 2016).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure of dipotassiumN-carbodithioato-L-prolinate trihydrate

Liebing

2017

Acta Cryst E

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“…The K-O bond distances relating to the oxygen atoms of the crown ether are in good agreement with those found in several X-ray structures of relevant macrocyclic complexes. 18 Additional oxygen donor interactions to the K + appear to be via the ethyl ester, using the ethyl oxygen in structure A and the carbonyl oxygen for structure B; the latter structure being ca. 4 kcal mol −1 more stable.…”

Section: Cation Binding Studies Ofmentioning

confidence: 99%

Functionalized fluorescent terephthalate monomers and their attempted polyester formation

et al. 2020

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“…The [30,32,33] As compared to the non-complexed salts, , [38] Na(S-2-C 5 H 4 N)(15c5) (102.1(1) pm), [38] K(S-2-C 5 H 4 N)(18c6) (77.27(6) pm), [38] K(OAc)(18c6) (77.98(4) pm), [39] Rb(SO 3 CF 3 )(18c6) (95.53(8) pm), [40] and Cs(SO 3 CF 3 )(18c6) (129.14(6) pm). [40]…”

Section: Resultsmentioning

confidence: 99%

The Alkali Metal Salts of Methyl Xanthic Acid

et al. 2020

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Methyl xanthates of the type M(SSC-OMe) (M = Li-Cs) are readily formed when carbon disulfide is reacted with the corresponding alkali metal hydroxides in methanol exposed to air, or with the alkali metal methoxides in dry methanol or THF under exclusion of air. The reactions are easily monitored by 13 C NMR spectroscopy. The Na, K, Rb, and Cs salt could be isolated in high yields, while the Li salt decomposed upon attempted isolation. All compounds are readily complexed by

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Crystal structures of two solvates of (18-crown-6)potassium acetate

Abstract: Hydrogen bonding plays an important role in the structures of two solvated forms of [K(18c6)]OAc (18c6 = 18-crown-6 = 1,4,7,10,13,16-hexaoxacyclooctadecane and OAc = acetate).

Cited by 11 publications

References 18 publications

Crystal structure of dipotassiumN-carbodithioato-L-prolinate trihydrate

Crystal structure of dipotassiumN-carbodithioato-L-prolinate trihydrate

Functionalized fluorescent terephthalate monomers and their attempted polyester formation

The Alkali Metal Salts of Methyl Xanthic Acid

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Crystal structures of two solvates of (18-crown-6)potassium acetate

Abstract: Hydrogen bonding plays an important role in the structures of two solvated forms of [K(18c6)]OAc (18c6 = 18-crown-6 = 1,4,7,10,13,16-hexa­oxa­cyclo­octa­decane and OAc = acetate).

Cited by 11 publications

References 18 publications

Crystal structure of dipotassiumN-carbodithioato-L-prolinate trihydrate

Crystal structure of dipotassiumN-carbodithioato-L-prolinate trihydrate

Functionalized fluorescent terephthalate monomers and their attempted polyester formation

The Alkali Metal Salts of Methyl Xanthic Acid

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Product

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Abstract: Hydrogen bonding plays an important role in the structures of two solvated forms of [K(18c6)]OAc (18c6 = 18-crown-6 = 1,4,7,10,13,16-hexaoxacyclooctadecane and OAc = acetate).