2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol

2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol
Names
	IUPAC name 3-tert-Butyl-2,2,4,4-tetramethylpentan-3-ol
Identifiers
CAS Number	41902-42-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	125760 ;
PubChem CID	142558;
CompTox Dashboard (EPA)	DTXSID80194673 ;
	InChI InChI=1S/C13H28O/c1-10(2,3)13(14,11(4,5)6)12(7,8)9/h14H,1-9H3 Key: LIUBOLYWYDGCSJ-UHFFFAOYSA-N ; InChI=1/C13H28O/c1-10(2,3)13(14,11(4,5)6)12(7,8)9/h14H,1-9H3 Key: LIUBOLYWYDGCSJ-UHFFFAOYAS;
	SMILES OC(C(C)(C)C)(C(C)(C)C)C(C)(C)C;
Properties
Chemical formula	C13H28O
Molar mass	200.366 g·mol−1
	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

2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol or tri-tert-butylcarbinol is an organic compound with formula C₁₃H₂₈O, ((H₃C)₃C)₃COH, or ^tBu₃COH.[1] It is an alcohol that can be viewed as a structural analog of a tridecane isomer (2,2,4,4-tetramethyl-3-t-butylpentane) where the central hydrogen has been replaced by a hydroxyl group -OH.

Tri-tert-butylcarbinol is arguably the most sterically hindered alcohol that has been prepared to date. In contrast to all other known alcohols, the infrared spectrum of the liquid does not exhibit a broad OH absorption associated with intermolecular hydrogen bonding, making it interesting for research in spectroscopy.[2] The bulky tert-butyl groups (H₃C)₃C- groups attached to the central carbon prevent the formation of a O–H---O hydrogen bond with another molecule, an intermolecular interaction typical of alcohols.

Another structural analog, in which the COH group is replaced by N, is tri-tert-butylamine, a molecule predicted to be stable but has never been prepared.

References

Z. Malarski (1974). "Solid rotator phases in 2,2,4,4-tetramethyl-3-tert-butyl-3-pentanol (t-Bu₃COH)". Mol. Cryst. Liq. Cryst. 25 (3–4): 259–272. doi:10.1080/15421407408082805.
Irena Majerza; Ireneusz Natkaniec (2006). "Experimental and theoretical IR, R, and INS spectra of 2,2,4,4-tetramethyl-3-t-butyl-pentane-3-ol". J. Mol. Struct. 788 (1–3): 93–101. doi:10.1016/j.molstruc.2005.11.022.

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[malar-1] Z. Malarski (1974). "Solid rotator phases in 2,2,4,4-tetramethyl-3-tert-butyl-3-pentanol (t-Bu₃COH)". Mol. Cryst. Liq. Cryst. 25 (3–4): 259–272. doi:10.1080/15421407408082805.

[maje-2] Irena Majerza; Ireneusz Natkaniec (2006). "Experimental and theoretical IR, R, and INS spectra of 2,2,4,4-tetramethyl-3-t-butyl-pentane-3-ol". J. Mol. Struct. 788 (1–3): 93–101. doi:10.1016/j.molstruc.2005.11.022.