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In terms of bonding, isocyanates are closely related to carbon dioxide (CO 2) and carbodiimides (C(NR) 2). The C−N=C=O unit that defines isocyanates is planar, and the N=C=O linkage is nearly linear. In phenyl isocyanate, the C=N and C=O distances are respectively 1.195 and 1.173 Å. The C−N=C angle is 134.9° and the N=C=O angle is 173.1°.
The C-N distance in isocyanides is 115.8 pm in methyl isocyanide.The C-N-C angles are near 180°. [3]Akin to carbon monoxide, isocyanides are described by two resonance structures, one with a triple bond between the nitrogen and the carbon and one with a double bond between.
The electronic structure is described most simply as :Ö̤−C≡N: with a single C−O bond and a triple C≡N bond. (Or more completely as :Ö̤−C≡N: ↔ Ö̤=C=N̤̈ ↔ :O≡C−N̤̈:) The infrared spectrum of a cyanate salt has a band at ca. 2096 cm −1; such a high frequency is characteristic of a triple bond. [2]
Toluene diisocyanate (TDI) is an organic compound with the formula CH 3 C 6 H 3 (NCO) 2.Two of the six possible isomers are commercially important: 2,4-TDI (CAS: 584-84-9) and 2,6-TDI (CAS: 91-08-7). 2,4-TDI is produced in the pure state, but TDI is often marketed as 80/20 and 65/35 mixtures of the 2,4 and 2,6 isomers respectively.
Tetramethylxylylene diisocyanate (TMXDI) is an organic compound with the formula C 6 H 4 (CMe 2 NCO) 2 (Me = CH 3).Introduced in the 1980s by American Cyanamid, the molecule features two isocyanate groups.
Phenyl isocyanate is an organic compound typically abbreviated PhNCO. The molecule consists of a phenyl ring attached to the isocyanate functional group. It is a colourless liquid that reacts with water. Phenyl isocyanate has a strong odor and tearing vapours, therefore it has to be handled with care.
Structure of Fe(tert-BuNC) 5.Notice that some C-N-C angles strongly deviate from 180°, a characteristic of low-valent isocyanide complexes. [8]Because of their low steric profile and high basicity, isocyanide ligands often install easily, e.g. by treating metal halides with the isocyanide.
Hydrogen isocyanide (HNC) is a linear triatomic molecule with C ∞v point group symmetry.It is a zwitterion and an isomer of hydrogen cyanide (HCN). [2] Both HNC and HCN have large, similar dipole moments, with μ HNC = 3.05 Debye and μ HCN = 2.98 Debye respectively. [3]