Names | |
---|---|
IUPAC name
Imidazolate
| |
Other names
Imidazolide
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
Properties | |
C3H3N2 | |
Molar mass | 67.070 |
Acidity (pKa) | 14.05 [1] |
Thermochemistry | |
Std enthalpy of
formation (ΔfH⦵298) |
67.8 kJ·mol−1 (16.2 kcal·mol−1) Gas phase. [2] |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Imidazolate (C3H3N−
2) is the conjugate base of
imidazole. It is a nucleophile and a strong base. The free anion has C2v
symmetry. Imidazole has a
pKa of 14.05,
[1] so the deprotonation of imidazole (C3H3N2H) requires a strong base.
Imidazolate is a common bridging ligand in coordination chemistry. In the zeolitic imidazolate frameworks, the metals are interconnected via imidazolates. [4] [5] In the enzyme superoxide dismutase, imidazolate links copper and zinc centers.
Names | |
---|---|
IUPAC name
Imidazolate
| |
Other names
Imidazolide
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
Properties | |
C3H3N2 | |
Molar mass | 67.070 |
Acidity (pKa) | 14.05 [1] |
Thermochemistry | |
Std enthalpy of
formation (ΔfH⦵298) |
67.8 kJ·mol−1 (16.2 kcal·mol−1) Gas phase. [2] |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Imidazolate (C3H3N−
2) is the conjugate base of
imidazole. It is a nucleophile and a strong base. The free anion has C2v
symmetry. Imidazole has a
pKa of 14.05,
[1] so the deprotonation of imidazole (C3H3N2H) requires a strong base.
Imidazolate is a common bridging ligand in coordination chemistry. In the zeolitic imidazolate frameworks, the metals are interconnected via imidazolates. [4] [5] In the enzyme superoxide dismutase, imidazolate links copper and zinc centers.