19497-26-8

Basic information

• Product Name: tributylammonium
• Synonyms: tributylammonium
• CAS NO: 19497-26-8
• Molecular Weight: 186.361
• Mol File: 19497-26-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tributylammonium(CAS DataBase Reference)
• NIST Chemistry Reference: tributylammonium(19497-26-8)
• EPA Substance Registry System: tributylammonium(19497-26-8)

Safety Data

• Hazardous Substances Data: 19497-26-8(Hazardous Substances Data)

Upstream product

• 102-82-9 tributyl-amine 
• 56577-69-6 Bis-(4-nitrophenyl)cyanomethane 
• 1610-26-0 1-nitro-4-(nitromethyl)benzene 
• 50985-90-5 tri(n-propyl)amine-H⁺ 
• 7310-95-4 2-Hydroxy-5-methylisophthalaldehyde 
• 17440-81-2 triethylammonium 

Downstream Products

• 102-82-9 tributyl-amine 
• 7310-95-4 2-Hydroxy-5-methylisophthalaldehyde 

Relevant articles and documents

Kinetic study of the reactions of various types of C-acids with amine bases in acetonitrile. An unusual effect of common BH+ cation on the rate constants

The rates of proton transfer reactions between C-acids of different types such as 1-(4-nitrophenyl)-1-nitroalkanes, 4-nitrophenylcyanomethanes, and 2,4,6-trinitrotoluene, and organic bases such as 1,1,3,3-tetrametylguanidine, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), and tri-n-butylamine have been measured in acetonitrile at pseudo-first-order conditions. A general equation for the rates of proton transfer reactions between C-acids and bases with product existing in two forms, ions and ion pairs, has been derived and its applicability tested. The equation works well except for reactions of 1-(4-nitrophenyl)-1-nitroalkanes with guanidines for which the second-order rate constant is diminished with concentration of guanidinium cation, while tetrabutylammonium salts accelerate the reactions. Possible reasons for this are discussed.

Entropy barriers to proton transfer

Proton transfer between sterically hindered pyridines and amines proceeds through locked-rotor, low-entropy intermediates. The reactions exhibit slow kinetics (efficiencies of 0.1-0.0001) and large negative temperature coefficients (up to k = CT-8.7). The rates become slower and the temperature dependencies steeper with increasing steric hindrance. The observations are reproduced by a multiple complex-switching RRKM model that allows several alternative complexes to be rate controlling: a series of loose complexes, a locked-rotor tight complex that occurs before the formation of a hydrogen-bonded complex, and a complex located at the central barrier. The rate-limiting transition state shifts from the loose to the tight and central-barrier complexes with increasing temperature. The model suggests that at elevated temperatures, above 1000 K, ion-molecule reactions will become slow even for unhindered, small reactants. Ion kinetics may then become similar to neutral radical kinetics.