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Citation: FENG Chang-Jun, WANG Chao, YANG Wei-Hua. The Quantitative Structure-Property Relationships Between the Topological Indices of Molecular Tree and pK_a Values of Carboxylic Acids[J]. Chinese Journal of Applied Chemistry, ;2004, 21(5): 469-474. shu

The Quantitative Structure-Property Relationships Between the Topological Indices of Molecular Tree and pK_a Values of Carboxylic Acids

1.
Department of Chemistry, Xuzhou Normal University, Xuzhou 221116

Corresponding author: FENG Chang-Jun,
Received Date: 20 June 2003
Available Online: 20 December 2003
Fund Project: 江苏省高校自然科学基金项目(02KJB150008) (02KJB150008)

A new acidity point valence(δⁱ^a) of non-hydrogen atom based on Randićs branching degree(δⁱ) is derived. A novel topological index(^m<F) of molecular tree and its trunk index(^m<F_c), leaf index(^m<Fx) are set up from δⁱ^a. The ⁰F_x, ⁰F_c,¹F_c and other structural parameters(,L,x',I) exhibit an excellent correlation to the acidity pK_a of 38 carboxylic acids. The best linear equation of heptvariant regression is proposed:pK_a= 11.409 33-1.243 27⁰F_x-0.617 23⁰F_c+0.097 00¹F_c-0.982 00x_p+1.283 71L-0.200 47x'-0.862 10I, R=0.987 1, S=0.168. The model could be used effectively to predict the pK_a values of carboxylic acids. Furthermore, a modified Jackknife test is used to validate the model robustness. On the basis of 12 structural parameters, a satisfactory equation of the pK_a has been obtained, whose correlation coefficient(R) and mean error(S) were 0.988 6 and 0.116, respectively. The correlativity is better than the results obtained from comparative molecular field analysis(CoMFA) reported in the literature, where R and S were 0.988 and 0.121, respectively.
- molecular tree,
- topological index,
- carboxylic acid,
- acid strength,
- quantitative structure-property relationship
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The Quantitative Structure-Property Relationships Between the Topological Indices of Molecular Tree and pKa Values of Carboxylic Acids

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通讯作者: 陈斌, bchen63@163.com

The Quantitative Structure-Property Relationships Between the Topological Indices of Molecular Tree and pK_a Values of Carboxylic Acids