15-Crown-5 is a crown ether with the formula (C2H4O)5. It is a cyclic pentamer of ethylene oxide that forms complex with various cations, including sodium (Na+)[2] and potassium (K+),[3] however, it is complementary to Na+ and thus has a higher selectivity for Na+ ions.

Skeletal formula
Ball-and-stick model
Systematic IUPAC name
3D model (JSmol)
ECHA InfoCard 100.046.694
EC Number 251-379-6
MeSH 15-Crown-5
RTECS number SB0200000
Molar mass 220.265 g·mol−1
Appearance Clear, colorless liquid
Density 1.113 g cm−3 (at 20 °C)
Boiling point 93–96 °C (199–205 °F; 366–369 K) at 0.05 mmHg
log P -0.639
-881.1--877.1 kJ mol−1
-5.9157--5.9129 MJ mol−1
Safety data sheet msds.chem.ox.ac.uk
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H302, H315, H319
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
Flash point 113 °C (235 °F; 386 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


Analogous to 18-crown-6, 15-crown-5 binds to sodium ions. Thus, when treated with this complexing agent, sodium salts often become soluble in organic solvents.

First-row transition metal dications fit snugly inside the cavity of 15-crown-5. They are too small to be included in 18-crown-6. The binding of transition metal cations results in multiple hydrogen-bonded interactions from both equatorial and axial aqua ligands, such that highly crystalline solid-state supramolecular polymers can be isolated. Metal salts isolated in this form include Co(ClO4)2, Ni(ClO4)2, Cu(ClO4)2, and Zn(ClO4)2. Seven coordinate species are most common for transition metal ions complexes of 15-crown-5, with the crown ether occupying the equatorial plane, along with 2 axial aqua ligands.[4]

Cobalt complex with 15-crown-5
The structure of the complex [Co(15-crown-5)(H2O)2]2+.

15-crown-5 has also been used to isolate salts of oxonium ions. For example, from a solution of tetrachloroauric acid, the oxonium ion [H7O3]+ has been isolated as the salt [(H7O3)(15-crown-5)2][AuCl4]. Neutron diffraction studies revealed a sandwich structure, which shows a chain of water with remarkably long O-H bond (1.12 Å) in the acidic proton, but with a very short OH•••O distance (1.32 Å).[4]

Structure of [(H7O3)(15-crown-5)2]+ ion

A derivative of 15-crown-5, benzo-15-crown-5, has been used to produce anionic complexes of carbido ligands as their [K(benzo-15-crown-5)2]+ salts:[4]

(Ar2N)3MoCH + KCH2Ph + 2 (15-crown-5) → [K(15-crown-5)2]+[(Ar2N)3MoC] + CH3Ph

See also


  1. ^ "15-crown-5 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 11 October 2011.
  2. ^ Takeda, Y.; et al. (1988). "A Conductance Study of 1:1 Complexes of 15-Crown-5, 16-Crown-5, and Benzo-15-crown-5 with Alkali Metal Ions in Nonaqueous Solvents". Bulletin of the Chemical Society of Japan. 61 (3): 627–632. doi:10.1246/bcsj.61.627.
  3. ^ Chen, Chun-Yen; et al. (2006). "Potassium ion recognition by 15-crown-5 functionalized CdSe/ZnS quantum dots in H2O". Chem. Comm. (3): 263–265. doi:10.1039/B512677K.
  4. ^ a b c Jonathan W. Steed; Jerry L. Atwood (2009). Supramolecular Chemistry, 2nd edition. Wiley. ISBN 978-0-470-51233-3.

Further reading

External links

Alkali metal

The alkali metals are a group (column) in the periodic table consisting of the chemical elements lithium (Li), sodium (Na), potassium (K), rubidium (Rb), caesium (Cs), and francium (Fr). This group lies in the s-block of the periodic table of elements as all alkali metals have their outermost electron in an s-orbital: this shared electron configuration results in their having very similar characteristic properties. Indeed, the alkali metals provide the best example of group trends in properties in the periodic table, with elements exhibiting well-characterised homologous behaviour.

The alkali metals are all shiny, soft, highly reactive metals at standard temperature and pressure and readily lose their outermost electron to form cations with charge +1. They can all be cut easily with a knife due to their softness, exposing a shiny surface that tarnishes rapidly in air due to oxidation by atmospheric moisture and oxygen (and in the case of lithium, nitrogen). Because of their high reactivity, they must be stored under oil to prevent reaction with air, and are found naturally only in salts and never as the free elements. Caesium, the fifth alkali metal, is the most reactive of all the metals. In the modern IUPAC nomenclature, the alkali metals comprise the group 1 elements, excluding hydrogen (H), which is nominally a group 1 element but not normally considered to be an alkali metal as it rarely exhibits behaviour comparable to that of the alkali metals. All the alkali metals react with water, with the heavier alkali metals reacting more vigorously than the lighter ones.

All of the discovered alkali metals occur in nature as their compounds: in order of abundance, sodium is the most abundant, followed by potassium, lithium, rubidium, caesium, and finally francium, which is very rare due to its extremely high radioactivity; francium occurs only in the minutest traces in nature as an intermediate step in some obscure side branches of the natural decay chains. Experiments have been conducted to attempt the synthesis of ununennium (Uue), which is likely to be the next member of the group, but they have all met with failure. However, ununennium may not be an alkali metal due to relativistic effects, which are predicted to have a large influence on the chemical properties of superheavy elements; even if it does turn out to be an alkali metal, it is predicted to have some differences in physical and chemical properties from its lighter homologues.

Most alkali metals have many different applications. One of the best-known applications of the pure elements is the use of rubidium and caesium in atomic clocks, of which caesium atomic clocks are the most accurate and precise representation of time. A common application of the compounds of sodium is the sodium-vapour lamp, which emits light very efficiently. Table salt, or sodium chloride, has been used since antiquity. Lithium finds use as a psychiatric medication. Sodium and potassium are also essential elements, having major biological roles as electrolytes, and although the other alkali metals are not essential, they also have various effects on the body, both beneficial and harmful.

Bunte salt

In organosulfur chemistry, a Bunte salt is an archaic name for salts with the formula RSSO3–Na+. These compounds are typically derived from alkylation on the pendant sulfur of sodium thiosulfate:

RX + Na2S2O3 → Na[O3S2R] + NaXThey are used as intermediates in the synthesis of thiols. They are also used to generate unsymmetrical disulfides:

Na[O3S2R] + NaSR' → RSSR' + Na2SO3According to X-ray crystallography, they adopt the expected structure with tetrahedral S(VI), an S-S single bond, and three S=O double bonds.

Crown ether

Crown ethers are cyclic chemical compounds that consist of a ring containing several ether groups. The most common crown ethers are cyclic oligomers of ethylene oxide, the repeating unit being ethyleneoxy, i.e., –CH2CH2O–. Important members of this series are the tetramer (n = 4), the pentamer (n = 5), and the hexamer (n = 6). The term "crown" refers to the resemblance between the structure of a crown ether bound to a cation, and a crown sitting on a person's head. The first number in a crown ether's name refers to the number of atoms in the cycle, and the second number refers to the number of those atoms that are oxygen. Crown ethers are much broader than the oligomers of ethylene oxide; an important group are derived from catechol.

Crown ethers strongly bind certain cations, forming complexes. The oxygen atoms are well situated to coordinate with a cation located at the interior of the ring, whereas the exterior of the ring is hydrophobic. The resulting cations often form salts that are soluble in nonpolar solvents, and for this reason crown ethers are useful in phase transfer catalysis. The denticity of the polyether influences the affinity of the crown ether for various cations. For example, 18-crown-6 has high affinity for potassium cation, 15-crown-5 for sodium cation, and 12-crown-4 for lithium cation. The high affinity of 18-crown-6 for potassium ions contributes to its toxicity. Crown ethers are not the only macrocyclic ligands that have affinity for the potassium cation. Ionophores such as valinomycin also display a marked preference for the potassium cation over other cations.

Crown ethers have been shown to coordinate to Lewis acids through electrostatic, σ-hole (see halogen bond) interactions, between the Lewis basic oxygen atoms of the crown ether and the electrophilic Lewis acid center.


Metallacrowns are a unique class of macrocyclic compounds that consist of metal ions and solely or predominantly heteroatoms in the ring. Classically, metallacrowns contain an [M–N–O] repeat unit in the macrocycle. First discovered by Vincent L. Pecoraro and Myoung Soo Lah in 1989, metallacrowns are best described as inorganic analogues of crown ethers. To date, over 600 reports of metallacrown research have been published. Metallacrowns with sizes ranging from 12-MC-4 to 60-MC-20 have been synthesized.In 2013, the project "Metallacrowns: Metallacrown-based innovative materials and supramolecular devices" has been funded by the European Union Research Executive Agency as a Marie Curie IRSES International Research Staff Exchange Scheme. This mobility project involves researchers from the Universities of Parma, Wrocław, Paris-Sud, Kyiv, and Michigan, and the CNRS in Orléans. This project has been funded by the European Community's Seventh Framework Programme (FP7/2007-2013) under grant agreement no. 611488.

Oxy-Cope rearrangement

In organic chemistry, the oxy-Cope rearrangement is a chemical reaction. It involves reorganization of the skeleton of certain unsaturated alcohols. It is a variation of the Cope rearrangement in which 1,5-dien-3-ols are converted to unsaturated carbonyl compounds by a mechanism typical for such a [3,3]-sigmatropic rearrangement.The reaction is highly general: a wide variety of precursors undergo the reorganization predictably and with ease, rendering it a highly useful synthetic tool. Further, production of the required starting material is often straightforward. The modification was first proposed in 1964 by Berson and Jones, who coined the term. The driving force is the formation of a carbonyl via spontaneous keto-enol tautomerization.

Base accelerates the reaction by 1010-1017, the anionic oxy-Cope rearrangement.

The formation of an enolate renders the reaction irreversible in most cases.


A polyrotaxane is a type of mechanically interlocked molecule consisting of strings and rings, in which multiple rings are threaded onto a molecular axle and prevented from dethreading by two bulky end groups. As oligomeric or polymeric species of rotaxanes, polyrotaxanes are also capable of converting energy input to molecular movements because the ring motions can be controlled by external stimulus. Polyrotaxanes have attracted much attention for decades, because they can help build functional molecular machines with complicated molecular structure.Although there are no covalent bonds between the axes and rings, polyrotaxanes are stable due to the high free activation energy (Gibbs energy) needed to be overcome to withdraw rings from the axes. Also, rings are capable of shuttling along and rotating around the axes freely, which leads to a huge amount of internal degree of freedom of polyrotaxanes. Due to this topologically interlocked structure, polyrotaxanes have many different mechanical, electrical, and optical properties compared to conventional polymers.Additionally the mechanically interlocked structures can be maintained in slide-ring materials, which are a type supramolecular network synthesized by crosslinking the rings (called figure-of-eight crosslinking) in different polyrotaxanes. In slide-ring materials, crosslinks of rings can pass along the axes freely to equalize the tension of the threading polymer networks, which is similar to pulleys. With this specific structure, slide-ring materials can be fabricated highly stretchable engineering materials due to their different mechanical properties.If the rings and axes are biodegradable and biocompatible, the polyrotaxanes can also be used for biomedical application, such as gene/drug delivery. The advantage of polyrotaxanes over other biomedical polymers, such as polysaccharides, is that because the interlocked structures are maintained by bulky stoppers at the ends of the strings, if the bulky stoppers are removed, such as removed by a chemical stimulus, rings dethread from the axes. The drastic structural change can be used for programmed drug or gene delivery, in which the drug or gene can be released with the rings when the stoppers are cut off at the specific destination.


Sodium is a chemical element with symbol Na (from Latin natrium) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table, because it has a single electron in its outer shell, which it readily donates, creating a positively charged ion—the Na+ cation. Its only stable isotope is 23Na. The free metal does not occur in nature, and must be prepared from compounds. Sodium is the sixth most abundant element in the Earth's crust and exists in numerous minerals such as feldspars, sodalite, and rock salt (NaCl). Many salts of sodium are highly water-soluble: sodium ions have been leached by the action of water from the Earth's minerals over eons, and thus sodium and chlorine are the most common dissolved elements by weight in the oceans.

Sodium was first isolated by Humphry Davy in 1807 by the electrolysis of sodium hydroxide. Among many other useful sodium compounds, sodium hydroxide (lye) is used in soap manufacture, and sodium chloride (edible salt) is a de-icing agent and a nutrient for animals including humans.

Sodium is an essential element for all animals and some plants. Sodium ions are the major cation in the extracellular fluid (ECF) and as such are the major contributor to the ECF osmotic pressure and ECF compartment volume. Loss of water from the ECF compartment increases the sodium concentration, a condition called hypernatremia. Isotonic loss of water and sodium from the ECF compartment decreases the size of that compartment in a condition called ECF hypovolemia.

By means of the sodium-potassium pump, living human cells pump three sodium ions out of the cell in exchange for two potassium ions pumped in; comparing ion concentrations across the cell membrane, inside to outside, potassium measures about 40:1, and sodium, about 1:10. In nerve cells, the electrical charge across the cell membrane enables transmission of the nerve impulse—an action potential—when the charge is dissipated; sodium plays a key role in that activity.

Stability constants of complexes

A stability constant (formation constant, binding constant) is an equilibrium constant for the formation of a complex in solution. It is a measure of the strength of the interaction between the reagents that come together to form the complex. There are two main kinds of complex: compounds formed by the interaction of a metal ion with a ligand and supramolecular complexes, such as host–guest complexes and complexes of anions. The stability constant(s) provide the information required to calculate the concentration(s) of the complex(es) in solution. There are many areas of application in chemistry, biology and medicine.

Transporter Classification Database

The Transporter Classification Database (or TCDB) is an International Union of Biochemistry and Molecular Biology (IUBMB)-approved classification system for membrane transport proteins, including ion channels.

Vincent L. Pecoraro

Vincent L. Pecoraro, professor at the University of Michigan, is a researcher in bioinorganic chemistry and inorganic chemistry. He is a specialist in the chemistry and biochemistry of manganese, vanadium, and metallacrown chemistry. He is a fellow of the American Association for the Advancement of Science

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