ESTIMATION OF PK(A) FOR ORGANIC OXYACIDS USING CALCULATED ATOMIC CHARGES

被引：90

作者：

DIXON, SL ^{[1
]}

JURS, PC ^{[1
]}

机构：

[1] PENN STATE UNIV,DEPT CHEM,UNIV PK,UNIV PK,PA 16802

来源：

JOURNAL OF COMPUTATIONAL CHEMISTRY | 1993年 / 14卷 / 12期

关键词：

D O I：

10.1002/jcc.540141208

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A method for the estimation of pK(a) from empirically calculated atomic charges has been developed and tested on a diverse set of organic oxyacids. The approach involves a comparison of the atomic charges calculated for both the acid and the negative ion that is formed after loss of the acidic proton. These charges have been used in conjunction with the familiar concepts of induction and resonance to develop an accurate formula to predict pK(a). Results for a set of 135 compounds, including alcohols, phenols, and carboxylic acids, yielded a fit of pK(a) with r = 0.993 and an rms error of 0.455. (C) 1993 by John Wiley & Sons, Inc.

引用

页码：1460 / 1467

页数：8

共 13 条

[1] CHARGE CALCULATIONS IN MOLECULAR MECHANICS .4. A GENERAL-METHOD FOR CONJUGATED SYSTEMS
ABRAHAM, RJ
SMITH, PE
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1988, 9 (04) : 288 - 297
[2] APPROACHES TO CHARGE CALCULATIONS IN MOLECULAR MECHANICS
ABRAHAM, RJ
GRIFFITHS, L
LOFTUS, P
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1982, 3 (03) : 407 - 416
[3] BARLIN GB, 1972, TECHNIQUES CHEM, V4, pCH9
[4] ATOMIC CHARGE CALCULATIONS FOR QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIPS
DIXON, SL
JURS, PC
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1992, 13 (04) : 492 - 504
[5] Hansch C., 1979, SUBSTITUENT CONSTANT
[6] Hine J., 1975, STRUCTURAL EFFECTS E
[7] A REEXAMINATION OF THE HAMMETT EQUATION
JAFFE, HH
[J]. CHEMICAL REVIEWS, 1953, 53 (02) : 191 - 261
[8] Leffler JE., 1989, RATES EQUILIBRIA ORG
[9] EFFICIENT METHOD FOR FINDING MINIMUM OF FUNCTION OF SEVERAL-VARIABLES WITHOUT CALCULATING DERIVATIVES
POWELL, MJD
[J]. COMPUTER JOURNAL, 1964, 7 (02) : 155 - &
[10] Sanderson R. T., 1960, CHEM PERIODICITY

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