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Citation: ZHANG Jian-Feng, HU Yue-Hua, WANG Dian-Zuo, WEI Dong-Zhi. Determination and Quantum Chemical Calculation of the Acid Dissociation Constants of Some Phenoxy Acetic Acids[J]. Chinese Journal of Applied Chemistry, ;2004, 21(8): 766-769. shu

Determination and Quantum Chemical Calculation of the Acid Dissociation Constants of Some Phenoxy Acetic Acids

1.
a Research Institute of Biochemistry, East China University of Science and Technology, Shanghai 200237;
2.
b School of Resources Processing and Bioengineering, Central South University, Changsha

Corresponding author: ZHANG Jian-Feng,
Received Date: 18 January 2004
Available Online: 11 June 2004
Fund Project: 国家重点基础研究发展规划资助项目(G1999064901) (G1999064901)

The acid dissociation constants of seven phenoxy acetic acids were determined by potentiometric titration. It has been shown that phenoxy acetic acids exhibit stronger acidity than both acetic acid and benzoic acid due to the induction and conjugation of the oxygen atom on -OCH₂COOH that links to the benzene ring. Acidity of phenoxy acetic acids containing two or more -OCH₂COOH groups is lower than that of phenoxy acetic acid by reason of electron donation of oxygen atom to the benzene ring. Quantum chemical calculation of the phenoxy acetic acids was carried out using CNDO/2 method. The bond charge density (ρ) of O-H and C-O bond in carboxyl group of seven phenoxy acetic acids was calculated, and the value f=ρ_O-H/ρ_C-O, was figured out. The f value of the carboxyl group in phenoxy acetic acid as well as the f values of the most likely dissociated carboxyl group in other six phenoxyl acetic acid derivatives are changed in the corresponding change order of their pK_a or pK_a1 values. It is concluded that the f value can be used as a judgement criterion of relative acidity for phenoxy acetic acids.
- phenoxy acetic acid,
- acid dissociation constant,
- bond charge density,
- quantum chemical calculation
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