Handbook for Estimating Physiochemical Properties of Organic Compounds

Martin Reinhard, Axel Drefahl0-471-17264-2, 9780471172642

A comprehensive compendium of published property estimation techniques for organic compounds. For scientists and engineers seeking to estimate properties of compounds, this time-saving Handbook brings together in one compact volume a vast array of property estimation methods from more than 2,700 published sources for calculating these and many other properties of organic compounds: * Density and molar volume * Boiling point * Refractive index and molar refraction * Melting point * Surface tension and parachor * Water solubility * Viscosity * * Air/water partition coefficient * Vapor pressure * Octanol/water partition coefficient * Enthalpy of vaporization * Soil/water partition coefficient. The property estimation techniques detailed in the Handbook have been chosen for their broad applicability and practical value. The discussion of each estimating technique includes a clear exposition of the technique, including classes of compounds for which it is applicable and critical consideration of its strengths and weaknesses, as well as many worked-out examples demonstrating the technique. The Handbook can be used on its own or in tandem with the Toolkit for Estimating Physicochemical Properties of Organic Compounds, an easy-to-use, Windows(r)-based program that puts rapid estimation routines and flexible search capabilities at the user’s fingertips. The Toolkit CD features routines for estimating key properties of organic compounds and a database of property and other data for more than 24,000 organic compounds. Also available: Toolkit for Estimating Physicochemical Properties of Organic Compounds ISBN 0-471-19492-1 (CD-ROM) * Toolkit for Estimating Physicochemical Properties of Organic Compounds ISBN 0-471-17263-4 (book/CD-ROM set)

---

Table of contents :
Front Matter……Page 1
Preface……Page 3
Table of Contents……Page 0
Front Matter……Page 4
Preface……Page 6
Table of Contents……Page 7
Purpose and Scope……Page 18
Classes of Estimation Methods……Page 19
Computer-aided Property Estimation……Page 22
1.2 Relationships between Isomeric Compounds……Page 23
Stereoisomers……Page 24
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
1.8 Nearest-neighbor Models……Page 38
1.9 Methods to Estimate Temperature-dependent Properties……Page 39
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