Can someone please tell me the pKa of the following carboxylic acids? 2-Hexyldecanoic acid, 2, 2-Dicyclohexylacetic acid and Adamantane carboxylic acid
Just use a software package to calculate the pKa values. It should give you an idea of the relative strengths of the acids. Pretty sure that Scifinder has one built in.
By first principles and through bond inductive effects, 2,2-dicyclohexylacetic acid and 2-hexyldecanoic acid will have a similar pKa of about 4.8. Presumably 1-Adamantane carboxylic acid would have a higher pKa of ~4.9-5.0
if u have pH of the following acids, u can calculate pKa values of them using Hasselsen Handerbalch equation pH= pKa + log [conjugate base]/[conjugate acid]
a) pKa = 4.81±0.10 (predicted); after: https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9227778.htm
b) pKa = 4.7 (predicted); after: T.M. Misiti, “Fate and Effect of Naphthenic Acids In Biological Systems”, PhD Thesis, Georgia Inst. of Technol., 2012, p. 206.
c) Gas phase acidity:
Article Acidities of substituted acetic acids
III. On the pKa of 1-adamantanecarboxylic acid (adamantane-3-carboxylic acid):
a) pKa = 4.86±0.20 (predicted); after: https://www.chemicalbook.com/ProductChemicalPropertiesCB3145173_EN.htm
b) pKa ≈ 4.9 (predicted); after: https://www.sciencedirect.com/science/article/pii/B9780123821614000042?via%3Dihub
c) Gas phase acidity:Article Intrinsic acidities of carboxylic acids from gas-phase acid ...
Can. J. Chem., 67(4) 1989, 611-618; https://doi.org/10.1139/v89-092