Chapter One Introduction ....................................................... 1
1.1 A database of the BDEs .................................................. 1
1.2 What is the BDE? ........................................................ 1
1.3 Why we need reliable BDEs ............................................... 2
1.4 Scope of this book ...................................................... 2
1.5 On energy units ......................................................... 3
1.6 How to search for BDEs in this book ..................................... 3
1.7 How to use the tables of the BDE data ................................... 4
Chapter Two Experimental methods for measuring BDEs ............................ 7
Chapter Three Tabulated BDEs of C-H bonds ..................................... 11
3.1 Chain saturated hydrocarbons ........................................... 11
3.2 Chain unsaturated hydrocarbons ......................................... 15
3.3 Cyclic hydrocarbons .................................................... 21
3.4 Aromatic hydrocarbons .................................................. 30
3.5 Halogenated hydrocarbons ............................................... 50
3.6 Organic compounds containing heteroatoms ............................... 57
3.6.1 C-H BDEs with α-OH, -OR, -C(O), and -C(O)O ....................... 57
3.6.2 C-H BDEs with α-N, -CN, -NO, -N02, and -NN ....................... 72
3.6.3 C-H BDEs with α-O, -N, and their groups .......................... 84
3.6.4 C-H BDEs with α-C(S), -S, -SO, and -S02 .......................... 89
3.6.5 C-H BDEs with other heteroatoms at α-position .................... 93
Chapter Four Tabulated BDEs of C-C bonds ...................................... 95
4.1 Saturated hydrocarbons ................................................. 95
4.2 Chain unsaturated hydrocarbons ........................................ 101
4.3 Aromatic hydrocarbons ................................................. 107
4.4 Halogenated hydrocarbons .............................................. 111
4.5 Organic compounds containing heteroatoms .............................. 119
4.5.1 Organic compounds containing oxygen atoms ....................... 119
4.5.2 Organic compounds containing nitrogen atoms ..................... 130
4.5.3 Organic compounds containing sulfur atoms ....................... 135
Chapter Five Tabulated BDEs of C-halogen bonds ............................... 139
5.1 C-F bonds ............................................................. 139
5.2 C-Cl bonds ............................................................ 142
5.3 C-Br bonds ............................................................ 151
5.4 C-I bonds ............................................................. 157
Chapter Six Tabulated BDEs of O-X bonds ...................................... 163
6.1 O-H bonds ............................................................. 163
6.1.1 O-H bonds in nonphenols ......................................... 163
6.1.2 O-H bonds in oximes and hydroxylamines .......................... 171
6.1.3 O-H bonds in phenols ............................................ 182
6.1.4 O-H bonds in sterically hindered phenols ........................ 195
6.2 O-O bonds ............................................................. 202
6.3 O-C bonds ............................................................. 205
6.3.1 O-C bonds in alcohols ........................................... 205
6.3.2 O-C bonds in ethers ............................................. 209
6.3.3 O-C bonds in esters, acids, and anhydrides ...................... 217
6.3.4 O-C bonds in peroxides and peroxys .............................. 220
6.3.5 O-C bonds in other species ...................................... 223
6.4 O-N bonds ............................................................. 225
6.5 O-S, O-halogen, and O-P bonds ......................................... 229
Chapter Seven Tabulated BDEs of N-X bonds .................................... 233
7.1 N-H bonds ............................................................. 233
7.1.1 N-H bonds in nonanilines ........................................ 233
7.1.2 N-H bonds in anilines ........................................... 240
7.1.3 N-H bonds in cyclic compounds ................................... 248
7.2 N-N bonds ............................................................. 254
7.3 N-C bonds ............................................................. 258
7.4 N-S bonds ............................................................. 269
7.5 N-halogen bonds ....................................................... 269
Chapter Eight Tabulated BDEs of S-X bonds .................................... 273
8.1 S-H bonds ............................................................. 273
8.2 S-S bonds ............................................................. 277
8.3 S-C bonds ............................................................. 279
8.4 S-halogen and S-P bonds ............................................... 285
Chapter Nine Tabulated BDEs of Si-, Ge-, Sn-, P-, and Se-X bonds ............. 287
9.1 Si-X bonds ............................................................ 287
9.2 Ge-X bonds ............................................................ 294
9.3 Sn-X bonds ............................................................ 296
9.4 P-X bonds ............................................................. 297
9.5 Se-X bonds ............................................................ 299
Chapter Ten Tabulated BDEs in some inorganic compounds ....................... 301
Chapter Eleven Heats of formation of atoms, inorganic and organic radicals ... 307
11.1 Gaseous atoms ........................................................ 307
11.2 Small inorganic radicals in the gas phase ............................ 308
11.3 Organic radicals in the gas phase .................................... 310
11.3.1 C-centered radicals ........................................... 310
11.3.2 O-centered radicals ........................................... 319
11.3.3 N-centered radicals ........................................... 321
11.3.4 S-centered radicals ........................................... 323
11.3.5 Si-, Ge-, and Sn-centered radicals ............................ 324
11.4 Group additivity values for organic radicals ......................... 325
11.4.1 GAVs of C/H radicals .......................................... 325
11.4.2 GAVs of O/C/H radicals ........................................ 326
11.4.3 GAVs of N/C/H/O radicals ...................................... 328
11.4.4 GAVs of S/C/H/O radicals ...................................... 329
References .................................................................... 331
Index of compound classes ..................................................... 361
Index of compound names ....................................................... 367
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