Hexapus, a new complexing agent for organic molecules

Menger, F. M.; Takeshita, Michihiro; Chow, J. F.

doi:10.1021/ja00409a067

Cited by 44 publications

(18 citation statements)

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“…[13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] Figure 5 shows a frequency plot of lg K a values for all the 973 complexes, whose aqueous association constants were reported in references [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27]. Complexes involving metal-containing hosts and/or charged guests have been excluded.…”

Section: Synthetic Hostsmentioning

confidence: 99%

“…The hosts include many of the most familiar organic receptors, some of which required special substituents to make them water-soluble: resorcinols, [13] resorcinarenes, [14] cyclophanes, [15] azacyclophanes, [16] ammonium cyclophanes, [17] crown ethers and their nitrogen analogues (macrocyclic polyamines), [18] calixarenes, [19] the cyclophanes of Dougherty and co-workers, [20] a macrocyclic derivative of Tröger's base, [21] flavinophanes, [22] metal-free porphyrins, [23] cyclotetrachromotropylene, [24] the aromatic hosts of Lehn and coworkers, [25] hexapus, [26] and cucurbituril [27] (Figure 6). The K a values are mostly within the range of 1 to 10 7 m À1 (see Figure 5).…”

Section: Synthetic Hostsmentioning

confidence: 99%

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Binding Affinities of Host–Guest, Protein–Ligand, and Protein–Transition‐State Complexes

et al. 2003

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The affinities of hosts—ranging from small synthetic cavitands to large proteins—for organic molecules are well documented. The average association constants for the binding of organic molecules by cyclodextrins, synthetic hosts, and albumins in water, as well as of catalytic antibodies or enzymes for substrates are 103.5±2.5 M−1. Binding affinities are elevated to 108±2 M−1 for the complexation of transition states and biological antigens by antibodies or inhibitors by enzymes, and to 1016±4 M−1 for transition states with enzymes. The origins of the distributions of association constants observed for the broad range of host–guest systems are explored in this Review, and typical approaches to compute and analyze host–guest binding in solution are discussed. In many classes of complexes a rough correlation is found between the binding affinity and the surface area that is buried upon complexation. Enzymes transcend this effect and achieve transition‐state binding much greater than is expected from the surface areas.

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Section: Synthetic Hostsmentioning

confidence: 99%

Section: Synthetic Hostsmentioning

confidence: 99%

Binding Affinities of Host–Guest, Protein–Ligand, and Protein–Transition‐State Complexes

et al. 2003

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“…In the present paper we report on the mesophases formed by yet another type of molecular architecture, namely of molecules consisting of a rigid central core with pyramidal symmetry to which long side chains are symmetrically bound at the pyramid base. The compound chosen consists of hexasubstituted tribenzocyclononene (2,3,7,8,12,13-hexasubstituted-5,10,15-dihydrotribenzo[a,d,g]cyclononene).…”

Section: Introductionmentioning

confidence: 99%

“…As may be seen from the structural formula, the central core of these series consist of a rigid crown structure with a trigonal pyramidal symmetry in which the three benzene rings form the three sides of the pyramid while the three methylene groups point towards its apex [5][6][7][8], The molecular structure is thus reminiscent of conventional discogenic compounds [1][2][3][4][9][10][11] except that their central core is no flat. As a result of this structure, symmetrically substituted homologues will in general possess a net electric dipole moment along the C 3 symmetry axis of the molecule.…”

Section: Introductionmentioning

confidence: 99%

Pyramidic Mesophases

Zimmermann

Poupko

Luz

et al. 1985

Zeitschrift Für Naturforschung A

159

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Two series of mesogenic compounds consisting of a rigid pyramidal central core and six equal flexible side chains were synthesized and their mesomorphic properties studied by calorimetry and optical microscopy. The two series of compounds are: I-hexaalkyloxytribenzocyclononene and II-hexaalkanoyloxytribenzocyclononene. In series I, enantiotropic mesophases appear for homologues in which the number, n, of carbon atoms in each side chain is equal or larger than six, while for series II mesomorphism is exhibited for all the compounds studied (8- 15). Some of these exhibit dimorphism (i.e. I-11 and II-12 to II-14) and even trimorphism (II-11). In total Five different mesophases are identified in both series. Several of these are stable at room temperature. Optical measurements indicate that they are not layered, they appear to be columnar. Due to the pyramidal shape of the central core of the constituent molecules special molecular arrangements for these mesophases are possible. It is suggested to call them pyramidic mesophases.

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“…Defined "oligomeric" surfactant structures obviously have stimulated the imagination of many colloid chemists, as a number of imaginative names were suggested for them: bola-surfactants [410][411][412], gemini-surfactants [413][414][415], tentacle molecules [416][417], octopus molecules [418], hexapus [419], multiarmed amphiphiles [420][421][422]. .…”

Section: Defined Oligomeric Surfactantsmentioning

confidence: 99%

Molecular concepts, self-organisation and properties of polysoaps

Laschewsky

Polysoaps/Stabilizers/Nitrogen-15 NMR

221

126

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The article reviews water-soluble polymers characterized by surfactant side chains, and related amphiphilic polymers. Various synthetic approaches are presented, and rules for useful molecular architectures are given. Models for the self-organization of such polymers in water are presented comparing them with the micellization of low molecular weight surfactants. Highlighting key properties of aqueous polysoap solutions such as viscosity, surface tension and solubilization power, some structure-property relationships are established. Further, the formation of mesophases and of superstructures in bulk is addressed. Finally, the functionalization of polysoaps, and potential applications are discussed.

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Hexapus, a new complexing agent for organic molecules

Cited by 44 publications

References 0 publications

Binding Affinities of Host–Guest, Protein–Ligand, and Protein–Transition‐State Complexes

Binding Affinities of Host–Guest, Protein–Ligand, and Protein–Transition‐State Complexes

Pyramidic Mesophases

Molecular concepts, self-organisation and properties of polysoaps

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