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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 journalArticleScientificpeer-review

Harvard

Taimoory, SM, Twum, K, Dashti, M, Pan, F, Lahtinen, M, Rissanen, K, Puttreddy, R, Trant, JF & Beyeh, NK 2020, 'Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes', Journal of Organic Chemistry, vol. 85, no. 9, pp. 5884-5894. https://doi.org/10.1021/acs.joc.0c00220

APA

Taimoory, S. M., Twum, K., Dashti, M., Pan, F., Lahtinen, M., Rissanen, K., ... Beyeh, N. K. (2020). Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes. Journal of Organic Chemistry, 85(9), 5884-5894. https://doi.org/10.1021/acs.joc.0c00220

Vancouver

Taimoory SM, Twum K, Dashti M, Pan F, Lahtinen M, Rissanen K et al. Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes. Journal of Organic Chemistry. 2020;85(9):5884-5894. https://doi.org/10.1021/acs.joc.0c00220

Author

Taimoory, S. Maryamdokht ; Twum, Kwaku ; Dashti, Mohadeseh ; Pan, Fangfang ; Lahtinen, Manu ; Rissanen, Kari ; Puttreddy, Rakesh ; Trant, John F. ; Beyeh, Ngong Kodiah. / Bringing a Molecular Plus One : Synergistic Binding Creates Guest-Mediated Three-Component Complexes. In: Journal of Organic Chemistry. 2020 ; Vol. 85, No. 9. pp. 5884-5894.

Bibtex - Download

@article{42ec6f9781a342fb89a7b3154ab4b602,
title = "Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes",
abstract = "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.",
author = "Taimoory, {S. Maryamdokht} and Kwaku Twum and Mohadeseh Dashti and Fangfang Pan and Manu Lahtinen and Kari Rissanen and Rakesh Puttreddy and Trant, {John F.} and Beyeh, {Ngong Kodiah}",
year = "2020",
doi = "10.1021/acs.joc.0c00220",
language = "English",
volume = "85",
pages = "5884--5894",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "AMER CHEMICAL SOC",
number = "9",

}

RIS (suitable for import to EndNote) - Download

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 -