. Author manuscript; available in PMC: 2010 Jun 19.

Published in final edited form as: J Org Chem. 2009 Jun 19;74(12):4433–4446. doi: 10.1021/jo900497s

Table 3.

Results for equation 1 compared to experimental ion pair pKs in THF. For compounds known to be aggregated (eg cesium enolates) the quoted pKs refer to the monomers.

RH Standard set	ΔE^a Kcal mol⁻¹	pK (THF)
Fluorene	0.0000	22.90^b
11 H-Benzo[a]fluorene	−4.6193	20.13^b
11 H-Benzo[b]fluorene	3.6544	23.63^b
7H–Benzo[c]fluorene	−5.8302	19.47^b
Benzo[def]fluorene	1.8526	22.91^b
9-Methylfluorene	1.6366	22.32^b
9-Phenylfluorene	−4.5744	18.15^b
9-tBuFluorene	2.5349	24.39^b
Triphenylmethane	16.4247	31.26^b
Phenalene	−4.7116	18.52^c
Benzanthrene	0.8934	21.48^c
Benzo[cd]pyrene	−0.4154	19.95^c
1,3-Diphenylpropene	12.0576	27.85^b
1,3-Diphenylindene	−13.6248	12.66^d
Delocalized
Diphenylmethane	11.5893	33.25^b
Toluene	24.6114	40.92^b
p-PhToluene	23.6189	38.73^b
Indene	−7.8107	19.79^e
Cyclopentadiene	−15.8297	16.11^f
Aryl
Benzene	35.2980	44.80^g,^h
p-fluorobenzene	33.2329	43.10^g,^h
m-fluorobenzene	31.2082	41.70^g,^h
2,6-difluorobenzene	11.6103	34.30^h
Acetylenic
Adamantylacetylene	6.2084	31.56ⁱ
Ketones
Bn₂CO	−16.9726	18.07^j
α-Tetralone	−0.7246	23.60^k
2-PhCyclohexanone	−8.9007	19.80^l
PhIsobutyrophenone	−0.1831	25.08^m
Acetophenone	−1.9777
Amines
Carbazole	−10.7763	19.24ⁿ
Ph2NH	−1.9869	24.20^o
Sulfur Cpds
Dithiane	14.3461	36.50^p
Phenyldithiane	10.6865	30.50^p
MeDithiane	19.0443	38.20^p
Trithiane^r	8.3652	30.20^p
Dimethyl Sulfone	−3.9859	28.80^q
Phenyl Methyl Sulfone	−2.1612	27.30^q