The purpose of this Handbook is to introduce the reader to the concept of property estimation, and to summarize property estimation methods use for important psychochemical properties. The number of estimation methods available in the literature is large and rapidly expanding. This book covers a subset judged by the authors to have relatively broad applicability and high practical value. A key word is judged, this book is not a literature review of all methods. In this regard, it is somewhat disheartening to see no mention of Sam Karikoff's early practical correlation of Koc to solubility and melting point. Knowing Martin, this omission is not an act of professional slight, but a consequence of efficiency in selecting recent, updated works because the later ones impacts directly on the goals of their Handbook. Nevertheless, readers, users and future generations will be unaware of Sam's contribution to the area of property prediction of environmentally relevant chemicals. He really popularized the subject publishing a key manuscript in 1979 and set the stage for high interest in the entire subject of predicting partition coefficients from thermodynamic properties. In addition, they will be unaware of his predecessor Ed Kanaga, who first proposed the idea to environmental chemists and engineers the previous year.. I reviewed an early manuscript of the book several years ago and liked it. This version is improved and some things of practical interest were included. My interest is primarily in Chapters 11 through 14, these subjects are: aqueous solubility, air-water partition coefficients (AWPC), 1-octanol water partition coefficients, and soil-water partition coefficients respectively. As an example of use of the Handbook I was particularly interested in AWPC estimation. These are found on pages 141-143 where four algorithms are reviewed and two are given. This is followed by the use of the method of Suzuki et al.; calculation details are given for determining Henry's constant for quinoline. The correlation is based on both molecular connectivity indices (MCI) and groups contributions. Additional statistical information is given about estimator algorithms useful to the practitioner. For the Suzuki et al. method: n=229, s=0.20 and r=0.994. This is a small book (228 pages), both handy and un-intimidating in size. It is filled with easy to use algorithms. Some, however, are easier than others. The group contribution approaches are more convenient to use than the MCI ones, in my opinion. It contains data in five appendixes. These include: density/temperature, vircosity temperatures, AWPC/temperatures, logs contributions, and Kow atom contributions. The full glossary in Appendix G is invaluable for using the algorithms effectively. The other chapter titles are: Overview of Property Estimation Methods; Computable Molecular Descriptiors; Density and Molar Volume; Refractive Index and Molar Refraction; Surface tension and Parachor Dynamic and Kinematic Viscosity; Vapor Pressure; Enthalpy of Vaporization; Boiling Point and Melting Point. Basically, thermodynamic things with viscosity being the only transport property covered. I wonder why they did not include molecular diffusivity as well. Knowing the physicochemical properties of organic chemicals is a prerequisite for many tasks met by chemical engineers and scientists. Chemical property estimation is the process of deriving an unknown property for a query compound from available properties, molecular descriptions, or reference compounds. The first chapter reviews the classes of estimation methods. Four general classes are covered, they include: quantitative property-property relationships (QPPRs); quantitative structure-property relationships (QSPRs); group contribution models (GCMs); and simlarity-based models. This overview chapter of theoretical approaches summaraizes the property estimation methods considered in the book. The remaining thirteen chapters are comprehensive compendium of published property estimation techniques for organic compounds for use by scientists and engineers seeking to estimate properties. The estimation methods have been carefully selected by the authors. Being highly respected researches in the subject area, they are well qualified to make this judgement.
Louis J. Thibodeaux, Jesse Coates Professor and Kallait T. Valsaraj, Associate Professor Gordon A. and Mary Cain Department of Chemical Engineering Louisiana State University Baton Rouge, LA 70803
Author(s): Martin Reinhard, Axel Drefahl
Edition: 1
Publisher: Wiley-Interscience
Year: 1998
Language: English
Commentary: +OCR
Pages: 255
Dependence on Solution pH......Page 1
Model of Bahnick and Doucette......Page 3
Table of Contents......Page 0
Model of Okouchi and Saegusa......Page 4
Extended Adjacency Matrix-Kow Relationships......Page 6
Model of Bodor, Gabanyi, and Wong......Page 7
Koc Estimation Using Kow......Page 2
Appendix B: Density-temperature Functions......Page 5
Method of Broto, Moreau, and Vandycke......Page 8
Method of Suzuki and Kudo......Page 10
Appendix C: Viscosity-temperature Functions......Page 11
Method of Hansch and Leo......Page 12
Appendix D: AWPC-temperature Functions......Page 14
Group Interchange Method of Drefahl and Reinhard......Page 15
1.8 Nearest-neighbor Models......Page 20
Appendix E: Contribution Values to Log S of Group Parameters in Models of Klopman et al.......Page 21
Computer-aided Property Estimation......Page 22
Method of Constantinou and Gani......Page 9
Method of Klopman and Wang......Page 13
11.8 Solubility in Seawater......Page 16
References......Page 17
Purpose and Scope......Page 18
Stereoisomers......Page 24
1.8 Nearest-neighbor Models......Page 38
1.9 Methods to Estimate Temperature-dependent Properties......Page 39
G.4 Abbreviations for Models, Methods, Algorithms, and Related Terms......Page 42
Classes of Estimation Methods......Page 19
1.2 Relationships between Isomeric Compounds......Page 23
Structure-property Relationship for Isomers......Page 25
1.3 Relationships between Homologous Compounds......Page 26
1.4 Quantitative Property-property Relationships......Page 28
1.5 Quantitative Structure-property Relationships......Page 29
1.6 Group Contribution Models......Page 30
Nonlinear GCMs......Page 32
1.7 Similarity-based and Group Interchange Models......Page 33
References......Page 40
2.1 Introduction......Page 43
Graph-theoretical Indices......Page 44
Cyclomatic Number of G......Page 45
2.2 Matrices Derived from the Adjacency Matrix......Page 46
Harary Index......Page 48
Charge Indices......Page 49
Indices Based on Atom-pair Weighting......Page 50
Delta Value Schemes and Molecular Connectivity Indices......Page 51
Cluster and Path-cluster MCis......Page 52
Physicochemical Properties as Computable Molecular Descriptors......Page 53
References......Page 54
3.1 Definitions and Applications......Page 56
3.2 Relationships between Isomers......Page 57
3.3.1 Homologous Series......Page 58
Correlations of Kier and Hall......Page 60
Correlation of Xu, Wang, and Su......Page 61
Scaled Volume Method of Girolami......Page 62
LOGIC Method......Page 63
Method of Constantinou, Gani, and O'Connell......Page 64
3.5 Temperature Dependence......Page 65
Method of Grain......Page 66
References......Page 67
4.1 Definitions and Applications......Page 71
4.3 Structure-RD Relationships......Page 72
Van der Waals Volume-molar Refraction Relationships......Page 73
Correlations of Kier and Hall......Page 74
Method of Ghose and Crippen......Page 75
References......Page 76
Parachor......Page 78
5.2 Property-property and Structure-property Relationships......Page 79
5.3 Group Contribution Approach......Page 80
Temperature Dependence of Parachor......Page 81
References......Page 82
6.1 Definitions and Applications......Page 84
6.2 Property-viscosity and Structure-viscosity Relationships......Page 85
6.3 Group Contribution Approaches for Viscosity......Page 86
Methods of Joback and Reid......Page 87
Method of Cao, Knudsen, Fredenslund, and Rasmussen......Page 88
Method of Mehrotra......Page 89
Grain's Method......Page 90
References......Page 91
7.1 Definitions and Applications......Page 93
Method of Mishra and Yalkowsky......Page 94
Method of Amidon and Anik......Page 95
Method of Macknick and Prausnitz......Page 96
Thomson's Method to Calculate Antoine Constants......Page 97
Methods to Estimate pv Solely from Molecular Structure......Page 99
References......Page 100
8.1 Definitions and Applications......Page 102
Homologous Series......Page 103
Wiener-index-DeltaHvb Relationship......Page 104
Molar Mass-DeltaHv Relationship......Page 105
Method of Ma and Zhao......Page 106
8.5 Temperature Dependence of DeltaHv......Page 107
References......Page 108
9.1 Definitions and Applications......Page 111
Correlation of Seybold......Page 112
MCI-boiling Point Relationships......Page 113
Correlation of Wessel and Jurs......Page 114
Graph-theoretical Indices-boiling Point Relationships......Page 115
Additivity in Rigid Aromatic Compounds......Page 116
Modified Joback Method......Page 117
Method of Stein and Brown......Page 118
Method of Wang, Milne, and Klopman......Page 119
Method of Constantinou and Gani......Page 120
Reduced-pressure Tb-structure Relationships......Page 121
References......Page 122
10.1 Definitions and Applications......Page 125
Estimation of Melting Points......Page 126
10.2 Homologous Series and Tm......Page 127
Method of Constantinou and Gani......Page 128
Methods of Joback and Reid......Page 129
10.4 Estimation of Tm Based on Molecular Similarity......Page 130
References......Page 133
11.1 Definition......Page 135
Ionic Strength......Page 136
11.2 Relationship between Isomers......Page 137
Function of Activity Coefficients and Crystallinity......Page 139
LSER of He, Wang, Han, Zhao, Zhang, and Zou......Page 141
Solubility-boiling Point Relationships......Page 142
11.5 Structure-solubility Relationships......Page 143
11.6 Group Contribution Approaches for Aqueous Solubility......Page 145
Method of Wakita, Yoshimoto, Miyamoto, and Watanabe......Page 146
11.7 Temperature Dependence of Aqueous Solubility......Page 148
Estimation from Henry's Law Constant......Page 149
Compounds with a Minimum in Their S(T) function......Page 150
11.8 Solubility in Seawater......Page 151
References......Page 152
12.1 Definitions......Page 157
12.3 Structure-AWPC Correlation......Page 158
Method of Suzuki, Ohtagushi, and Koide......Page 159
12.5 Temperature Dependence of AWPC......Page 160
References......Page 163
13.1 Definitions and Applications......Page 165
Dependence on Solution pH......Page 166
Solubility-Kow Correlations......Page 167
Collander-type Relationships......Page 168
Chromatographic Parameter-Kow Relationships......Page 169
Chlorine Number-Kow Relationships......Page 170
Extended Adjacency Matrix-Kow Relationships......Page 171
Model of Bodor, Gabanyi, and Wong......Page 172
Method of Broto, Moreau, and Vandycke......Page 173
Method of Suzuki and Kudo......Page 175
Method of Hansch and Leo......Page 177
Method of Klopman and Wang......Page 178
Method of Klopman, Li, Wang, and Dimayuga......Page 179
Group Interchange Method of Drefahl and Reinhard......Page 180
References......Page 183
14.1 Definition......Page 188
Koc Estimation Using Kow......Page 190
Model of Bahnick and Doucette......Page 191
Model of Okouchi and Saegusa......Page 192
References......Page 193
Appendix A: Smiles notation: Brief Tutorial......Page 195
Appendix B: Density-temperature Functions......Page 200
Appendix C: Viscosity-temperature Functions......Page 206
Appendix D: AWPC-temperature Functions......Page 209
Appendix E: Contribution Values to Log S of Group Parameters in Models of Klopman et al.......Page 216
Appendix F: Kow Atom Contributions of Broto et al.......Page 219
G.1 Property and Physical State Notations......Page 233
G.2 Molecular Descriptor Notations......Page 234
G.4 Abbreviations for Models, Methods, Algorithms, and Related Terms......Page 237
A......Page 240
B......Page 241
C......Page 242
D......Page 243
G......Page 244
I......Page 246
L......Page 247
M......Page 248
O......Page 249
P......Page 250
S......Page 251
T......Page 253
V......Page 254
X......Page 255
