Handbook for Estimating Physicochemical Properties of Organic Compounds M Reinhard and A Drefahl

Martin Reinhard, Axel Drefahl0471172642, 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)

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Table of contents :
Cover Page……Page 1
Title Page……Page 2
ISBN 0471172642……Page 3
Preface……Page 4
1. Overview of Property Estimation Methods……Page 5
2. Computable Molecular Descriptors……Page 6
4. Refractive Index and Molar Refraction……Page 7
6. Dynamic and Kinematic Viscosity……Page 8
8. Enthalpy of Vaporization……Page 9
9. Boiling Point……Page 10
11. Aqueous Solubility……Page 11
12. Air-water Partition Coefficient……Page 12
13. 1-octanol-water Partition Coefficient……Page 13
Appendices……Page 14
Index……Page 15
Purpose and Scope……Page 16
Classes of Estimation Methods……Page 17
Computer-aided Property Estimation……Page 20
1.2 Relationships between Isomeric Compounds……Page 21
Stereoisomers……Page 22
Structure-property Relationship for Isomers……Page 23
1.3 Relationships between Homologous Compounds……Page 24
1.4 Quantitative Property-property Relationships……Page 26
1.5 Quantitative Structure-property Relationships……Page 27
1.6 Group Contribution Models……Page 28
Nonlinear GCMs……Page 30
1.7 Similarity-based and Group Interchange Models……Page 31
1.8 Nearest-neighbor Models……Page 36
1.9 Methods to Estimate Temperature-dependent Properties……Page 37
References……Page 38
2.1 Introduction……Page 41
Graph-theoretical Indices……Page 42
Cyclomatic Number of G……Page 43
2.2 Matrices Derived from the Adjacency Matrix……Page 44
Harary Index……Page 46
Charge Indices……Page 47
Indices Based on Atom-pair Weighting……Page 48
Delta Value Schemes and Molecular Connectivity Indices……Page 49
Cluster and Path-cluster MCis……Page 50
Physicochemical Properties as Computable Molecular Descriptors……Page 51
References……Page 52
3.1 Definitions and Applications……Page 54
3.2 Relationships between Isomers……Page 55
3.3.1 Homologous Series……Page 56
Correlations of Kier and Hall……Page 58
Correlation of Xu, Wang, and Su……Page 59
Scaled Volume Method of Girolami……Page 60
LOGIC Method……Page 61
Method of Constantinou, Gani, and O’Connell……Page 62
3.5 Temperature Dependence……Page 63
Method of Grain……Page 64
References……Page 65
4.1 Definitions and Applications……Page 69
4.3 Structure-RD Relationships……Page 70
Van der Waals Volume-molar Refraction Relationships……Page 71
Correlations of Kier and Hall……Page 72
Method of Ghose and Crippen……Page 73
References……Page 74
Parachor……Page 76
5.2 Property-property and Structure-property Relationships……Page 77
5.3 Group Contribution Approach……Page 78
Temperature Dependence of Parachor……Page 79
References……Page 80
6.1 Definitions and Applications……Page 82
6.2 Property-viscosity and Structure-viscosity Relationships……Page 83
6.3 Group Contribution Approaches for Viscosity……Page 84
Methods of Joback and Reid……Page 85
Method of Cao, Knudsen, Fredenslund, and Rasmussen……Page 86
Method of Mehrotra……Page 87
Grain’s Method……Page 88
References……Page 89
7.1 Definitions and Applications……Page 91
Method of Mishra and Yalkowsky……Page 92
Method of Amidon and Anik……Page 93
Method of Macknick and Prausnitz……Page 94
Thomson’s Method to Calculate Antoine Constants……Page 95
Methods to Estimate pv Solely from Molecular Structure……Page 97
References……Page 98
8.1 Definitions and Applications……Page 100
Homologous Series……Page 101
Wiener-index-DeltaHvb Relationship……Page 102
Molar Mass-DeltaHv Relationship……Page 103
Method of Ma and Zhao……Page 104
8.5 Temperature Dependence of DeltaHv……Page 105
References……Page 106
9.1 Definitions and Applications……Page 109
Correlation of Seybold……Page 110
MCI-boiling Point Relationships……Page 111
Correlation of Wessel and Jurs……Page 112
Graph-theoretical Indices-boiling Point Relationships……Page 113
Additivity in Rigid Aromatic Compounds……Page 114
Modified Joback Method……Page 115
Method of Stein and Brown……Page 116
Method of Wang, Milne, and Klopman……Page 117
Method of Constantinou and Gani……Page 118
Reduced-pressure Tb-structure Relationships……Page 119
References……Page 120
10.1 Definitions and Applications……Page 123
Estimation of Melting Points……Page 124
10.2 Homologous Series and Tm……Page 125
Method of Constantinou and Gani……Page 126
Methods of Joback and Reid……Page 127
10.4 Estimation of Tm Based on Molecular Similarity……Page 128
References……Page 131
11.1 Definition……Page 133
Ionic Strength……Page 134
11.2 Relationship between Isomers……Page 135
Function of Activity Coefficients and Crystallinity……Page 137
LSER of He, Wang, Han, Zhao, Zhang, and Zou……Page 139
Solubility-boiling Point Relationships……Page 140
11.5 Structure-solubility Relationships……Page 141
11.6 Group Contribution Approaches for Aqueous Solubility……Page 143
Method of Wakita, Yoshimoto, Miyamoto, and Watanabe……Page 144
11.7 Temperature Dependence of Aqueous Solubility……Page 146
Estimation from Henry’s Law Constant……Page 147
Compounds with a Minimum in Their S(T) function……Page 148
11.8 Solubility in Seawater……Page 149
References……Page 150
12.1 Definitions……Page 155
12.3 Structure-AWPC Correlation……Page 156
Method of Suzuki, Ohtagushi, and Koide……Page 157
12.5 Temperature Dependence of AWPC……Page 158
References……Page 161
13.1 Definitions and Applications……Page 163
Dependence on Solution pH……Page 164
Solubility-Kow Correlations……Page 165
Collander-type Relationships……Page 166
Chromatographic Parameter-Kow Relationships……Page 167
Chlorine Number-Kow Relationships……Page 168
Extended Adjacency Matrix-Kow Relationships……Page 169
Model of Bodor, Gabanyi, and Wong……Page 170
Method of Broto, Moreau, and Vandycke……Page 171
Method of Suzuki and Kudo……Page 173
Method of Hansch and Leo……Page 175
Method of Klopman and Wang……Page 176
Method of Klopman, Li, Wang, and Dimayuga……Page 177
Group Interchange Method of Drefahl and Reinhard……Page 178
References……Page 181
14.1 Definition……Page 186
Koc Estimation Using Kow……Page 188
Model of Bahnick and Doucette……Page 189
Model of Okouchi and Saegusa……Page 190
References……Page 191
Appendix A: Smiles notation: Brief Tutorial……Page 193
Appendix B: Density-temperature Functions……Page 198
Appendix C: Viscosity-temperature Functions……Page 204
Appendix D: AWPC-temperature Functions……Page 207
Appendix E: Contribution Values to Log S of Group Parameters in Models of Klopman et al…….Page 214
Appendix F: Kow Atom Contributions of Broto et al…….Page 217
G.1 Property and Physical State Notations……Page 231
G.2 Molecular Descriptor Notations……Page 232
G.4 Abbreviations for Models, Methods, Algorithms, and Related Terms……Page 235
A……Page 238
B……Page 239
C……Page 240
D……Page 241
G……Page 242
I……Page 244
L……Page 245
M……Page 246
O……Page 247
P……Page 248
S……Page 249
T……Page 251
V……Page 252
X……Page 253
Back Page……Page 254