1361091-53-3Relevant academic research and scientific papers
Substituent effects in double-helical hydrogen-bonded AAA-DDD complexes
Wang, Hong-Bo,Mudraboyina, Bhanu P.,Wisner, James A.
supporting information; experimental part, p. 1322 - 1327 (2012/03/26)
Two series of DDD and AAA hydrogen-bond arrays were synthesized that form triply-hydrogenbonded double-helical complexes when combined in CDCl3 solution. Derivatization of the DDD arrays with electron- withdrawing groups increases the complex association constants by up to a factor of 30 in those arrays examined. Derivatization of the AAA arrays with electron donating substituents reveals a similar magnitude effect on the complex stabilities. The effect of substitution on both types of arrays are modeled quite satisfactorily (R2 > 0.96 in all cases) as free energy relationships with respect to the sums of their Hammett substituent constants. In all, the complex stabilities can be manipulated over more than three orders of magnitude (>20 kJmol-1) using this type of modification.
