Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes
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Bringing a Molecular Plus One : Synergistic Binding Creates Guest-Mediated Three-Component Complexes. / Taimoory, S. Maryamdokht; Twum, Kwaku; Dashti, Mohadeseh; Pan, Fangfang; Lahtinen, Manu; Rissanen, Kari; Puttreddy, Rakesh; Trant, John F.; Beyeh, Ngong Kodiah.
In: Journal of Organic Chemistry, Vol. 85, No. 9, 2020, p. 5884-5894.Research output: Contribution to journal › Article › Scientific › peer-review
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TY - JOUR
T1 - Bringing a Molecular Plus One
T2 - Synergistic Binding Creates Guest-Mediated Three-Component Complexes
AU - Taimoory, S. Maryamdokht
AU - Twum, Kwaku
AU - Dashti, Mohadeseh
AU - Pan, Fangfang
AU - Lahtinen, Manu
AU - Rissanen, Kari
AU - Puttreddy, Rakesh
AU - Trant, John F.
AU - Beyeh, Ngong Kodiah
PY - 2020
Y1 - 2020
N2 - Cethyl-2-methylresorcinarene (A), pyridine (B), and a set of 10 carboxylic acids (Cn) associate to form A·B·Cn ternary assemblies with 1:1:1 stoichiometry, representing a useful class of ternary systems where the guest mediates complex formation between the host and a third component. Although individually weak in solution, the combined strength of the multiple noncovalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution, as explored by both experimental and computational methods. The interactions between A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions between A and B, demonstrating positive cooperativity. Our results reveal that the two-component system such as that formed by A and B can form the basis for the development of specific sensors for the molecular recognition of carboxylic acids.
AB - Cethyl-2-methylresorcinarene (A), pyridine (B), and a set of 10 carboxylic acids (Cn) associate to form A·B·Cn ternary assemblies with 1:1:1 stoichiometry, representing a useful class of ternary systems where the guest mediates complex formation between the host and a third component. Although individually weak in solution, the combined strength of the multiple noncovalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution, as explored by both experimental and computational methods. The interactions between A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions between A and B, demonstrating positive cooperativity. Our results reveal that the two-component system such as that formed by A and B can form the basis for the development of specific sensors for the molecular recognition of carboxylic acids.
U2 - 10.1021/acs.joc.0c00220
DO - 10.1021/acs.joc.0c00220
M3 - Article
VL - 85
SP - 5884
EP - 5894
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 9
ER -