3-Hexyne

3-Hexyne

Skeletal formula
Ball-and-stick model
Names
IUPAC name Hex-3-yne
Other names Diethylacetylene
Identifiers
CAS Number	928-49-4 Y
ChemSpider	12979 Y
Jmol 3D model	Interactive image Interactive image
PubChem	13568
InChI InChI=1S/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3 Y Key: DQQNMIPXXNPGCV-UHFFFAOYSA-N Y InChI=1/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3 Key: DQQNMIPXXNPGCV-UHFFFAOYAF
SMILES C(#CCC)CC CCC#CCC
Properties
Chemical formula	C6H10
Molar mass	82.14 g/mol
Appearance	Colorless liquid
Density	0.723 g/cm3
Melting point	−105 °C (−157 °F; 168 K)
Boiling point	81 to 82 °C (178 to 180 °F; 354 to 355 K)
Solubility in water	low
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

3-Hexyne is the organic compound with the formula C₂H₅CCC₂H₅, simplified to C₆H₁₀. This colorless liquid is the most common of the three isomeric hexynes. Together with 2-butyne and diphenylacetylene, it serves as a reference acetylenic ligand in organometallic chemistry. 3-Hexyne is useful because the ¹H NMR signals for the methylene bridges convey stereochemical information in its octahedral complexes.

Properties

Spectral characteristics

In a proton NMR spectroscopy result, 3-hexyne produces a triplet of integrated area 6H at a chemical shift of approximately 1.0 ppm and a quartet of integrated area 4H at approximately 2.2 ppm. The less deshielded triplet corresponds to the terminal methyl hydrogen atoms that experience spin-spin splitting from the adjacent methylene hydrogen atoms. The quartet corresponds to the more deshielded methylene hydrogen atoms that are spin-spin split by the adjacent methyl hydrogen atoms. The methylene hydrogens don't form a complex multiplet because the internal alkyne function that is adjacent to them does not contain any bonded hydrogen atoms with which they can interact. The overall symmetry of the molecule causes both methylene bridges to contain hydrogen atoms in exactly the same electronic environment. The same logic follows to explain the identical spectroscopic results provided by the hydrogen atoms on all methyl groups.