0000000001299856
AUTHOR
John F. Trant
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…
Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies
Host–guest complexes of C-hexyl-2-bromoresorcinarene (BrC6) with twelve potential aromatic N-oxide guests were studied using single crystal X-ray diffraction analysis and 1H NMR spectroscopy. In the solid state, of the nine obtained X-ray crystal structures, eight were consistent with the formation of BrC6-N-oxide endo complexes. The lone exception was from the association between 4-phenylpyridine N-oxide and BrC6, in that case the host forms a self-inclusion complex. BrC6, as opposed to more rigid previously studied C-ethyl-2-bromoresorcinarene and C-propyl-2-bromoresorcinarene, undergoes remarkable cavity conformational changes to host different N-oxide guests through C–H···π(host) intera…
High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor
N-Alkyl ammonium resorcinarenes selectively bind pyrophosphate in pure water with an exceptionally high binding constant of up to 1.60 × 107 M–1, three orders of magnitude higher than ATP.
Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides*
The host-guest complexes of C-propyl-2-bromoresorcinarene with pyridine N-oxide, 3-methylpyridine N-oxide, quinoline N-oxide and isoquinoline N-oxide are studied using single crystal X-ray crystallography and 1H NMR spectroscopy. The C-propyl-2-bromoresorcinarene forms endo-complexes with the aromatic N-oxides in the solid-state when crystallised from either methanol or acetone. In solution, the endo-complexes were observed only in methanol-d4. In DMSO the solvent itself is a good guest, and crystallisation provides only solvate endo-complexes. The C-propyl-2-bromoresorcinarene shows remarkable flexibility when crystallised from either methanol or acetone, and packs into one-dimensional sel…
Halogen-bonded solvates of tetrahaloethynyl cavitands
The formation and structures of halogen-bonded solvates of three different tetrahaloethynyl cavitands with acetone, chloroform, acetonitrile, DMF and DMSO were prepared and investigated. The inclusion and host–guest behaviour of the resorcinarene cavitands was found to be highly dependent on the flexibility of the ethylene-bridging unit.
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
Bamboo-like Chained Cavities and Other Halogen-Bonded Complexes from Tetrahaloethynyl Cavitands with Simple Ditopic Halogen Bond Acceptors
Halogen bonding provides a useful complement to hydrogen bonding and metal-coordination as a tool for organizing supramolecular systems. Resorcinarenes, tetrameric bowl-shaped cavitands, have been previously shown to function as efficient scaffolds for generating dimeric capsules in both solution and solid-phase, and complicated one-, two-, and three-dimensional frameworks in the solid phase. Tetrahaloethynyl resorcinarenes (bromide and iodide) position the halogen atoms in a very promising “crown-like” orientation for acting as organizing halogen-bond donors to help build capsules and higher-order networks. Symmetric divalent halogen bond acceptors including bipyridines, 1,4-dioxane, and 1…
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…
Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides*
The host-guest complexes of C-propyl-2-bromoresorcinarene with pyridine N-oxide, 3-methylpyridine N-oxide, quinoline N-oxide and isoquinoline N-oxide are studied using single crystal X-ray crystallography and 1H NMR spectroscopy. The C-propyl-2-bromoresorcinarene forms endo-complexes with the aromatic N-oxides in the solid-state when crystallised from either methanol or acetone. In solution, the endo-complexes were observed only in methanol-d4. In DMSO the solvent itself is a good guest, and crystallisation provides only solvate endo-complexes. The C-propyl-2-bromoresorcinarene shows remarkable flexibility when crystallised from either methanol or acetone, and packs into one-dimensional sel…
Endo-/exo- and halogen-bonded complexes of conformationally rigid C-ethyl-2-bromoresorcinarene and aromatic N-oxides
The host-guest complexes of conformationally rigid C-ethyl-2-bromoresorcinarene with aromatic N-oxides were studied using single crystal X-ray crystallography. Unlike that of the conformationally more flexible C-ethyl-2-methylresorcinarene, the C-ethyl-2-bromoresorcinarene cavity forms endo-complexes only with the small pyridine-N-oxides, such as pyridine N-oxide, 2-methyl-, 3-methyl- and 4-methylpyrdine N-oxide, and quinoline N-oxide. The larger 2,4,6-trimethylpyridine, 4-phenylpyridine and isoquinoline N-oxide, and 4,4-bipyridine N,N′-dioxide and 1,3-bis(4-pyridyl)propane N,N′-dioxide do not fit into the host cavity. Instead endo-acetone complexes are formed. Remarkably, differing from th…
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…
Halogen bonding and host–guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests
Single crystal X-ray structures of halogen-bonded assemblies formed between host N-hexylammonium resorcinarene bromide (1) or N-cyclohexylammonium resorcinarene chloride (2), and 1,4-diiodooctafluorobutane and accompanying small solvent guests (methanol, acetonitrile and water) are presented. The guests’ inclusion affects the geometry of the cavity of the receptors 1 and 2, while the divalent halogen bond donor 1,4-diiodooctafluorobutane determines the overall nature of the halogen bond assembly. The crystal lattice of 1 contains two structurally different dimeric assemblies A and B, formally resulting in the mixture of a capsular dimer and a dimeric pseudo-capsule. 1H and 19F NMR analyses …
CCDC 1551407: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
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 1551402: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
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 1556027: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K
CCDC 1583123: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
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 1551412: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
CCDC 1583131: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
CCDC 1556030: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K
CCDC 1583125: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
CCDC 1556033: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K
CCDC 1583130: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
CCDC 1551404: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
CCDC 1583128: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
CCDC 1574172: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, John F. Trant, Robin H. A. Ras, Kari Rissanen|2018|Cryst.Growth Des.|18|513|doi:10.1021/acs.cgd.7b01517
CCDC 1551411: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
CCDC 1574174: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, John F. Trant, Robin H. A. Ras, Kari Rissanen|2018|Cryst.Growth Des.|18|513|doi:10.1021/acs.cgd.7b01517
CCDC 1556029: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K
CCDC 1551410: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
CCDC 1583127: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
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 1551408: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
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 1556032: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K
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 1551406: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
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 1551403: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
CCDC 1574171: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, John F. Trant, Robin H. A. Ras, Kari Rissanen|2018|Cryst.Growth Des.|18|513|doi:10.1021/acs.cgd.7b01517
CCDC 1894767: Experimental Crystal Structure Determination
Related Article: Fangfang Pan, Mohadeseh Dashti, Michael R. Reynolds, Kari Rissanen, John F. Trant, Ngong Kodiah Beyeh|2019|Beilstein J.Org.Chem.|15|947|doi:10.3762/bjoc.15.91
CCDC 1583124: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
CCDC 1556028: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K
CCDC 1551405: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
CCDC 1583126: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
CCDC 1583122: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
CCDC 1894766: Experimental Crystal Structure Determination
Related Article: Fangfang Pan, Mohadeseh Dashti, Michael R. Reynolds, Kari Rissanen, John F. Trant, Ngong Kodiah Beyeh|2019|Beilstein J.Org.Chem.|15|947|doi:10.3762/bjoc.15.91
CCDC 1583129: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurcek, Lotta Turunen, John F. Trant, Robin H. A. Ras and Kari Rissanen|2017|Supramol.Catal.|30|445|doi:10.1080/10610278.2017.1414217
CCDC 1551401: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E
CCDC 1556031: Experimental Crystal Structure Determination
Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K
CCDC 1551409: Experimental Crystal Structure Determination
Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H. A. Ras, John F. Trant, Kari Rissanen|2017|CrystEngComm|19|4312|doi:10.1039/C7CE00975E