. Author manuscript; available in PMC: 2012 Apr 1.

Published in final edited form as: J Org Chem. 2010 Oct 18;75(22):7651–7658. doi: 10.1021/jo1014646

TABLE 6.

1:1 Hydrogen Bond Association Constants in Water at 298 K

H-bond acid	H-bond base	K	log K	α^H₂	β^H₂	α^H₂*β^H₂	Ref
phenol	acetate	0.47	−0.328	0.596	2.930	1.746	34
formic acid	formate	0.25	−0.602	0.700	2.500	1.750	34
acetic acid	acetate	0.40	−0.398	0.580	2.930	1.699	34
RNH₃⁺	phenolate	0.20	−0.700	1.400	2.120	2.968	34
phenol	pyridine	0.60	−0.222	0.596	0.625	0.373	33
4-methylphenol	pyridine	0.69	−0.161	0.569	0.625	0.356	33
2-iodophenol	pyridine	0.57	−0.244	0.400	0.625	0.250	33
4-iodophenol	pyridine	0.61	−0.215	0.679	0.625	0.424	33