The Determination of the Association Constants of Some Acid Amides in Benzene Solution

Hobbs, Marcus E.; Bates, W. W.

doi:10.1021/ja01123a047

Cited by 26 publications

(12 citation statements)

References 5 publications

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“…m-Substituted benzamides showed the highest association constants among the molecules studied. 38 An IR study of primary amides suggested that they may associate into clusters larger than dimers at higher concentrations in CCl 4 . 39 The first recognition of self-assembly and the production of nanoscopic objects among primary amide-containing molecules in solution was performed using 3,4,5-tris(octyloxy)benzamide, which displays liquid crystalline properties, as discussed previously (Fig.…”

Section: Self-assembly In Solutionmentioning

confidence: 99%

Self-assembly driven by an aromatic primary amide motif

2012

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Primary amides are unique supramolecular synthons possessing two hydrogen donors and two hydrogen acceptors. By interacting in a complementary fashion, primary amides reliably generate two-dimensional hydrogen bonded networks that differ from conventional hydrogen bonded structures such as carboxylic acid dimers or one-dimensional secondary amide chains. This feature permits the design of sophisticated supramolecular assemblies based on primary amides (especially aromatic amides). Several interesting crystal structures have been constructed utilizing primary amides, although such structures have been applied only in the field of crystal engineering because the networks strongly favor crystallization. Expansion of the applications of primary amides to liquid crystals and self-assembly in solution requires an appropriate balance between primary amide-based hydrogen bonding and other noncovalent interactions. This perspective article reviews the key hydrogen bonding properties of primary amides determined from crystal structure studies, and a variety of supramolecular assemblies involving primary amides are discussed. A new strategy for overcoming crystallinity and solubility issues is proposed, involving introduction of a trifluoromethyl group at the ortho position of the aromatic primary amide. Such substitutions produce highly processable primary amides, while maintaining the two-dimensional hydrogen bonded network. Examples of self-assembly using 2-trifluoromethylbenzamide demonstrate its usefulness in self-assembly.

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Section: Self-assembly In Solutionmentioning

confidence: 99%

Self-assembly driven by an aromatic primary amide motif

2012

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“…Ultrasonic velocity in liquids and liquid mixes, as well as its influence on molecular structure, was extensively researched. Ultrasonic velocity measurements have been used to identify and determine stronger and weaker molecular interactions in binary and ternary liquid combinations [12][13][14][15][16][17][18]. At a temperature of 293.15K and 298.15K, ultrasonic velocity, density, and viscosity measurements of liquids, both pure and mixed were carried out to establish various acoustic parameters such as Adiabatic compressibility, Intermolecular free length, Acoustic Impedance, Ultrasonic Attenuation, Relaxation Time, Relative association and Gibb's Free Energy.…”

Section: Introductionmentioning

confidence: 99%

Inter-molecular investigation of polyethylene glycols in methanol and butylparaben mixture to compute volumetric and acoustic parameters at 293.15 & 298.15 k temperature

Thakur

Anand²,

Kumari³

2022

J. Phys.: Conf. Ser.

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Acoustic parameters such as acoustic impedance, intermolecular free length, adiabatic compressibility, relative association, and Gibb’s free energy of polyethylene glycols of molecular weight 200 and 600 in methanol butylparaben solution were investigated using ultrasonic velocity and density measurements at temperatures T=293.15 and 298.15k and experimental pressure p=0.1MPa. The acoustic parameters adiabatic compressibility and intermolecular free length obey the same pattern as these measured parameters; however, the parameter acoustic impedance follows the opposite trend. In the current scheme under investigation, there are strong interactions between the solute and solvent molecules.

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“…Based on our previous work, using primary aromatic amides as hydrogen bonding motifs, we synthesized a terpolymer composed of methyl methacrylate (MMA), 2-((3,5-bis(4-carbamoyl-3-(trifluoromethyl)phenoxy)benzyloxy)carbonylamino)ethyl methacrylate as a dendritic benzamide-containing methacrylate (BMA), and lauryl methacrylate (LMA) by reversible addition–fragmentation chain transfer (RAFT) copolymerization. LMA was introduced as a long alkyl chain-containing monomer to facilitate solubility in toluene. ,, To form self-assembled nanostructures, BMA containing dendritic benzamide was selected for its multi-valent and self-complementary hydrogen bonding units. − A benzamide group has an association constant on the order of 40–300 M –1 and has been used for the construction of various supramolecular structures . While the terpolymer showed good solubility in tetrahydrofuran (THF), which is a good solvent to every repeating unit, the solubility of the polymer in toluene at RT and 50 °C varied depending on the composition because of the degree of complimentary hydrogen bonds between the benzamides …”

Section: Introductionmentioning

confidence: 99%

“…LMA was introduced as a long alkyl chain-containing monomer to facilitate solubility in toluene. ,, To form self-assembled nanostructures, BMA containing dendritic benzamide was selected for its multi-valent and self-complementary hydrogen bonding units. − A benzamide group has an association constant on the order of 40–300 M –1 and has been used for the construction of various supramolecular structures . While the terpolymer showed good solubility in tetrahydrofuran (THF), which is a good solvent to every repeating unit, the solubility of the polymer in toluene at RT and 50 °C varied depending on the composition because of the degree of complimentary hydrogen bonds between the benzamides …”

Section: Introductionmentioning

confidence: 99%

Viscosifying a Noncovalently Joined Polymer Nanoparticle Solution upon Heating

Shin

Seo

2020

Macromolecules

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We report the synthesis of a series of statistical terpolymer poly[(methyl methacrylate)-co-lauryl methacrylate-co-2-((3,5-bis(4-carbamoyl-3-(trifluoromethyl)phenoxy)benzyloxy)carbonylamino)ethyl methacrylate] (P(MMA-co-LMA-co-BMA)) by reversible addition–fragmentation chain transfer polymerization and their aggregation behaviors in solution. In toluene, the solution behavior of terpolymer was controlled by the molar fractions of lauryl methacrylate (LMA) and benzamide-containing methacrylate (BMA) in the polymer, which increased solubility and promoted hydrogen bonding between the primary aromatic amides, respectively. Temperature-dependent 1H NMR spectroscopy also indicated gradual dissociation of the hydrogen bonds with increasing temperature. For the polymer containing 2.7 mol % of LMA and 2.7 mol % of BMA repeating units, we demonstrated that dissolving the polymer in tetrahydrofuran as a good solvent and switching the solvent with toluene produced polymer nanoparticles with diameters of several tens of nanometers, as observed by dynamic light scattering. Intramolecular hydrogen bonding was dominant and induced the noncovalent chain collapse. When the temperature of the particle dispersion in toluene at a concentration > 30 mg/mL was increased from RT to 50 °C, a significant increase in viscosity was observed. This behavior was not observed in a toluene solution of poly(methyl methacrylate), which showed decreased viscosity at a higher temperature. The viscosity increase was accompanied by a decrease in the particle size, and both were attributed to the dissociation of some intramolecular hydrogen bonds within the particles, which can increase the number of individual chains in toluene and result in more intermolecular interactions.

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The Determination of the Association Constants of Some Acid Amides in Benzene Solution

Cited by 26 publications

References 5 publications

Self-assembly driven by an aromatic primary amide motif

Self-assembly driven by an aromatic primary amide motif

Inter-molecular investigation of polyethylene glycols in methanol and butylparaben mixture to compute volumetric and acoustic parameters at 293.15 & 298.15 k temperature

Viscosifying a Noncovalently Joined Polymer Nanoparticle Solution upon Heating

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