2,2'-Dipyridylamine

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2,2′-Dipyridylamine
Dipyridylamine.png
Names
Preferred IUPAC name
N-(Pyridin-2-yl)pyridin-2-amine
Other names
2,2′-Iminodipyridine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.013.513 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-864-3
PubChem CID
UNII
  • InChI=1S/C10H9N3/c1-3-7-11-9(5-1)13-10-6-2-4-8-12-10/h1-8H,(H,11,12,13)
    Key: HMMPCBAWTWYFLR-UHFFFAOYSA-N
  • C1=CC=NC(=C1)NC2=CC=CC=N2
Properties
C10H9N3
Molar mass 171.203 g·mol−1
Appearancewhite solid
Melting point 90.5 °C (194.9 °F; 363.6 K)
Boiling point 307.5 °C (585.5 °F; 580.6 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,2′-Dipyridylamine is an organic compound with the formula (C5H4N)2NH. It consists of a pair of 2-pyridyl groups (C5H4N) linked to a secondary amine. The compound forms a range of coordination complexes. [1] Its conjugate base, 2,2′-dipyridylamide, forms extended metal atom chains. [2]

Formation

2,2′-Dipyridylamine can be formed by heating pyridine with sodium amide. Alternatively, 2-aminopyridine can be heated with 2-chloropyridine over barium oxide. [3]

Related Research Articles

<span class="mw-page-title-main">Coordination complex</span> Molecule or ion containing ligands datively bonded to a central metallic atom

A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the coordination centre, and a surrounding array of bound molecules or ions, that are in turn known as ligands or complexing agents. Many metal-containing compounds, especially those that include transition metals, are coordination complexes.

Cuprates are a class of compounds that contain copper (Cu) atom(s) in an anion. They can be broadly categorized into two main types:

<span class="mw-page-title-main">Phosphorine</span> Chemical compound

Phosphorine is a heavier element analog of pyridine, containing a phosphorus atom instead of an aza- moiety. It is also called phosphabenzene and belongs to the phosphaalkene class. It is a colorless liquid that is mainly of interest in research.

<span class="mw-page-title-main">Bipyridine</span> Group of chemical compounds

Bipyridines are a family of organic compounds with the formula (C5H4N)2, consisting of two pyridyl (C5H4N) rings. Pyridine is an aromatic nitrogen-containing heterocycle. The bipyridines are all colourless solids, which are soluble in organic solvents and slightly soluble in water. Bipyridines, especially the 4,4' isomer, are mainly of significance in pesticides.

<span class="mw-page-title-main">Terpyridine</span> Chemical compound

Terpyridine is a heterocyclic compound derived from pyridine. It is a white solid that is soluble in most organic solvents. The compound is mainly used as a ligand in coordination chemistry.

<span class="mw-page-title-main">1,10-Phenanthroline</span> Heterocyclic organic compound

1,10-Phenanthroline (phen) is a heterocyclic organic compound. It is a white solid that is soluble in organic solvents. The 1,10 refer to the location of the nitrogen atoms that replace CH's in the hydrocarbon called phenanthrene.

<span class="mw-page-title-main">Diethylenetriamine</span> Chemical compound

Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.

<span class="mw-page-title-main">2,2′-Bipyridine</span> Chemical compound

2,2′-Bipyridine (bipy or bpy, pronounced ) is an organic compound with the formula C10H8N2. This colorless solid is an important isomer of the bipyridine family. It is a bidentate chelating ligand, forming complexes with many transition metals. Ruthenium and platinum complexes of bipy exhibit intense luminescence, which may have practical applications.

<span class="mw-page-title-main">Tris(bipyridine)ruthenium(II) chloride</span> Chemical compound

Tris(bipyridine)ruthenium(II) chloride is the chloride salt coordination complex with the formula [Ru(bpy)3]Cl2. This polypyridine complex is a red crystalline salt obtained as the hexahydrate, although all of the properties of interest are in the cation [Ru(bpy)3]2+, which has received much attention because of its distinctive optical properties. The chlorides can be replaced with other anions, such as PF6.

<span class="mw-page-title-main">Acetylenedicarboxylic acid</span> Chemical compound

Acetylenedicarboxylic acid or butynedioic acid is an organic compound with the formula H2C4O4 or HO−C(=O)−C≡C−C(=O)−OH. It is a crystalline solid that is soluble in diethyl ether.

<span class="mw-page-title-main">BTBP</span> A class of tetradentate ligand compounds

The bis-triazinyl bipyridines (BTBPs) are a class of chemical compounds which are tetradentate ligands similar in shape to quaterpyridine. The BTBPs are made by the reaction of hydrazine and a 1,2-diketone with 6,6'-dicyano-2,2'-bipyridine. The dicyanobipy can be made by reacting 2,2'-bipy with hydrogen peroxide in acetic acid, to form 2,2'-bipyridine-N,N-dioxide. The 2,2'-bipyridine-N,N-dioxide is then converted into the dicyano compound by treatment with potassium cyanide and benzoyl chloride in a mixture of water and THF.

<span class="mw-page-title-main">2-Mercaptopyridine</span> Chemical compound

2-Mercaptopyridine is an organosulfur compound with the formula HSC5H4N. This yellow crystalline solid is a derivative of pyridine. The compound and its derivatives serve primarily as acylating agents. A few of 2-mercaptopyridine's other uses include serving as a protecting group for amines and imides as well as forming a selective reducing agent. 2-Mercaptopyridine oxidizes to [[2,2-dipyridyl disulfide]].

<span class="mw-page-title-main">Chromium(VI) oxide peroxide</span> Chemical compound

Chromium(VI) oxide peroxide is the name given to a collection of chromium coordination complexes. They have the formula CrO(O2)2L where L is a ligand. These species are dark blue and often labile. They all feature oxo ligand and two peroxo ligands, with the remaining coordination sites occupied by water, hydroxide, ether, or other Lewis bases.

In chemistry, tetradentate ligands are ligands that bind four donor atoms to a central atom to form a coordination complex. This number of donor atoms that bind is called denticity and is a method of classifying ligands.

<span class="mw-page-title-main">2,2'-Dipyrromethene</span> Chemical compound

2,2'-Dipyrromethene, often called just dipyrromethene or dipyrrin, is a chemical compound with formula C
9
H
8
N
2
whose skeleton can be described as two pyrrole rings C
5
N
connected by a methyne bridge =CH– through their nitrogen-adjacent (position-2) carbons; the remaining bonds being satisfied by hydrogen atoms. It is an unstable compound that is readily attacked by nucleophilic compounds above −40 °C.

<i>cis</i>-Dichlorobis(bipyridine)ruthenium(II) Chemical compound

cis-Dichlorobis(bipyridine)ruthenium(II) is the coordination complex with the formula RuCl2(bipy)2, where bipy is 2,2'-bipyridine. It is a dark green diamagnetic solid that is a precursor to many other complexes of ruthenium, mainly by substitution of the two chloride ligands. The compound has been crystallized as diverse hydrates.

<span class="mw-page-title-main">Transition metal pyridine complexes</span>

Transition metal pyridine complexes encompass many coordination complexes that contain pyridine as a ligand. Most examples are mixed-ligand complexes. Many variants of pyridine are also known to coordinate to metal ions, such as the methylpyridines, quinolines, and more complex rings.

Transition metal complexes of 2,2'-bipyridine are coordination complexes containing one or more 2,2'-bipyridine ligands. Complexes have been described for all of the transition metals. Although few have any practical value, these complexes have been influential. 2,2'-Bipyridine is classified as a diimine ligand. Unlike the structures of pyridine complexes, the two rings in bipy are coplanar, which facilitates electron delocalization. As a consequence of this delocalization, bipy complexes often exhibit distinctive optical and redox properties.

Manganese(III) chloride is the hypothetical inorganic compound with the formula MnCl3.

Cobalt compounds are chemical compounds formed by cobalt with other elements.

References

  1. Wang, Suning (2001). "Luminescence and electroluminescence of Al(III), B(III), Be(II) and Zn(II) complexes with nitrogen donors". Coordination Chemistry Reviews. 215: 79–98. doi:10.1016/S0010-8545(00)00403-3.
  2. Cotton, F. Albert; Daniels, Lee M.; Jordan; Murillo, Carlos A. (1997). "Symmetrical and Unsymmetrical Compounds Having a Linear Co36+ Chain Ligated by a Spiral Set of Dipyridyl Anions". Journal of the American Chemical Society. 119 (43): 10377–10381. doi:10.1021/JA971997H.
  3. Brogden, David W.; Berry, John F. (4 September 2015). "Coordination Chemistry of 2,2′-Dipyridylamine: The Gift That Keeps on Giving". Comments on Inorganic Chemistry. 36 (1): 17–37. doi:10.1080/02603594.2015.1079522. S2CID   101638568.