0000000001010001
AUTHOR
Kwaku Twum
Host–Guest Interactions of Sodiumsulfonatomethyleneresorcinarene and Quaternary Ammonium Halides: An Experimental–Computational Analysis of the Guest Inclusion Properties
The molecular recognition of nine quaternary alkyl- and aryl-ammonium halides (Bn) by two different receptors, Calkyl-tetrasodiumsulfonatomethyleneresorcinarene (An), were studied in solution using...
Sharing the salt bowl: counterion identity drives N-alkyl resorcinarene affinity for pyrophosphate in water
N-Alkyl ammonium resorcinarene chloride receptors, NARX4, have been shown to act as high-sensitivity detectors of pyrophosphate (PPi), a biomarker of disease, in aqueous media through the chloride-to-PPi exchange [NAR(Cl)4 to NARPPi]. The nature of the anion of the macrocyclic NARX4 (X = Cl−, Br−, triflate OTf−) receptor greatly influences the PPi-affinity in aqueous media. The binding affinity for [NAR (Cl)4] is 3.61 × 105 M−1, while the NAR (Br)4 and NAR (OTf)4 show stronger binding of 5.30 × 105 M−1, and 6.10 × 105 M−1, respectively. The effects of upper rim ammonium cation, –N+H2R substituents (R = 3-hydroxypropyl, cyclohexyl, benzyl, or napththalen-1-ylmethyl), of the macrocyclic resor…
The “nitrogen effect” : Complexation with macrocycles potentiates fused heterocycles to form halogen bonds in competitive solvents
Weak intermolecular forces are typically very difficult to observe in highly competitive polar protic solvents as they are overwhelmed by the quantity of competing solvent. This is even more challenging for three-component ternary assemblies of pure organic compounds. In this work, we overcome these complications by leveraging the binding of fused aromatic N-heterocycles in an open resorcinarene cavity to template the formation of a three-component halogen-bonded ternary assembly in a protic polar solvent system. peerReviewed
Host-Guest Interactions of Sodiumsulfonatomethyleneresorcinarene and Quaternary Ammonium Halides : An Experimental-Computational Analysis of the Guest Inclusion Properties
The molecular recognition of nine quaternary alkyl- and aryl-ammonium halides (Bn) by two different receptors, Calkyl-tetrasodiumsulfonatomethyleneresorcinarene (An), were studied in solution using 1H NMR spectroscopy. Substitution of methylenesulfonate groups at 2-positions of resorcinol units resulted in an increase of cavity depth by ∼2.80 Å and a narrow cavity aperture compared to Calkyl-2-H-resorcinarenes. The effect of alkyl chain lengths on the endo-complexation, that is the ability to incorporate other than N-methyl chains inside the cavities, were investigated using ammonium cations of the type ⁺NH2(R1)(R2), (R1 = Me, Et, Bu, R2 = Bu, Ph, Bz ). The C−H⋯ interactions between guests …
Recent Advances in Halogen Bonded Assemblies with Resorcin[4]arenes
Resorcinarenes are cavity-containing compounds when in the crown conformation, from the calixarene family of concave compounds. These easy to synthesize macrocycles can be decorated at the upper rim through the eight hydroxyl groups and/or the 2-position of the aromatic ring. They are good synthons in supramolecular chemistry leading to appealing assemblies such as open-inclusion complexes, capsules and tubes through multiple weak interactions with various guests. Halogen bonding (XB) is a highly directional non-covalent interaction by an electron-deficient halogen atom as a donor that interacts with a Lewis base, the XB acceptor. This tutorial review provides an overview of recent advances…
Bringing a Molecular Plus One : Synergistic Binding Creates Guest-Mediated Three-Component Complexes
C-Ethyl-2-Methylresorcinarene (A), pyridine (B), and a set of ten 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 non-covalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution as explored by both experimental and computational methods. The interactions be-tween A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions b…
Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes
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 betw…
CCDC 1938867: Experimental Crystal Structure Determination
Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220
CCDC 1966175: Experimental Crystal Structure Determination
Related Article: Kwaku Twum, J. Mikko Rautiainen, Shilin Yu, Khai-Nghi Truong, Jordan Feder, Kari Rissanen, Rakesh Puttreddy, Ngong Kodiah Beyeh|2020|Cryst.Growth Des.|20|2367|doi:10.1021/acs.cgd.9b01540
CCDC 2231744: Experimental Crystal Structure Determination
Related Article: Kwaku Twum, Sanaz Nadimi, Frank Boateng Osei, Rakesh Puttreddy, Yvonne Bessem Ojong, John J. Hayward, Kari Rissanen, John F. Trant, Ngong Kodiah Beyeh|2023|Chem.Asian J.|18|e202201308|doi:10.1002/asia.202201308
CCDC 1938870: Experimental Crystal Structure Determination
Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220
CCDC 1938871: Experimental Crystal Structure Determination
Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220
CCDC 1966174: Experimental Crystal Structure Determination
Related Article: Kwaku Twum, J. Mikko Rautiainen, Shilin Yu, Khai-Nghi Truong, Jordan Feder, Kari Rissanen, Rakesh Puttreddy, Ngong Kodiah Beyeh|2020|Cryst.Growth Des.|20|2367|doi:10.1021/acs.cgd.9b01540
CCDC 1938873: Experimental Crystal Structure Determination
Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220
CCDC 1938868: Experimental Crystal Structure Determination
Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220
CCDC 1938872: Experimental Crystal Structure Determination
Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220
CCDC 1938866: Experimental Crystal Structure Determination
Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220
CCDC 1938869: Experimental Crystal Structure Determination
Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220
CCDC 1966171: Experimental Crystal Structure Determination
Related Article: Kwaku Twum, J. Mikko Rautiainen, Shilin Yu, Khai-Nghi Truong, Jordan Feder, Kari Rissanen, Rakesh Puttreddy, Ngong Kodiah Beyeh|2020|Cryst.Growth Des.|20|2367|doi:10.1021/acs.cgd.9b01540
CCDC 1966173: Experimental Crystal Structure Determination
Related Article: Kwaku Twum, J. Mikko Rautiainen, Shilin Yu, Khai-Nghi Truong, Jordan Feder, Kari Rissanen, Rakesh Puttreddy, Ngong Kodiah Beyeh|2020|Cryst.Growth Des.|20|2367|doi:10.1021/acs.cgd.9b01540
CCDC 1966172: Experimental Crystal Structure Determination
Related Article: Kwaku Twum, J. Mikko Rautiainen, Shilin Yu, Khai-Nghi Truong, Jordan Feder, Kari Rissanen, Rakesh Puttreddy, Ngong Kodiah Beyeh|2020|Cryst.Growth Des.|20|2367|doi:10.1021/acs.cgd.9b01540