Exploring the relationship between the conformation and pK_a: can a pK_a value be used to determine the conformational equilibrium?

TY - JOUR

T1 - Exploring the relationship between the conformation and pKa

T2 - can a pKa value be used to determine the conformational equilibrium?

AU - Olsen, Jacob Ingemar

AU - Sauer, Stephan P. A.

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2015/3/14

Y1 - 2015/3/14

N2 - Four substituted cis and trans-4,5-dihydroxyhexahydropyridazines that were expected to undergo pH induced conformational switching were synthesized and carefully investigated by NMR analyses and calculations. For two of the compounds a large difference in pKa existed between the two possible chair conformers and for one compound this resulted in conformational switching as a result of pH change. For the first time it is shown that the pKa directly reflects the conformational equilibrium of conformers.

AB - Four substituted cis and trans-4,5-dihydroxyhexahydropyridazines that were expected to undergo pH induced conformational switching were synthesized and carefully investigated by NMR analyses and calculations. For two of the compounds a large difference in pKa existed between the two possible chair conformers and for one compound this resulted in conformational switching as a result of pH change. For the first time it is shown that the pKa directly reflects the conformational equilibrium of conformers.

U2 - 10.1039/C4OB02630F

DO - 10.1039/C4OB02630F

M3 - Journal article

SN - 1470-4358

VL - 13

SP - 3116

EP - 3121

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 10

ER -