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a's of the hydrogen bond donors and acceptors in organic solvents (refs 3 and 10 and references therein).
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15844368513
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13] minimizes complications from ion-pairing effects (see Experimental Section).
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H bond represents the free energy of hydrogen bond formation in the monoanion and is a lower limit of the difference in free energy of the hydrogen bond in the anionic vs the acid species.
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2-BA would be correspondingly lowered by 2 units. This lowers the estimated stabilization from one and two hydrogen bonds to values of 6.5 and 11.7 kcal/mol, respectively. The corrected value of 11.7 kcal/mol remains similar to the value of 13.0 kcal/mol expected from an additive effect.
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note
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We thank John Griffin and members of the Herschlag lab for comments on the manuscript. This work is supported by grants from the Lucille P. Markey Charitable Trust and the Chicago Community Trust to D.H. D.H. is a Lucille P. Markey Scholar and a Searle Scholar.
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