Abstract:The strength of a weak intramolecular hydrogen bond was quantified using molecular torsion balances and found to vary between -0.99 kcal/mol and +1.00 kcal/mol due to solvation. Analyzing the results...
“…According to Kamlet–Taft parameters, it is conceivable that the formation constant for hydrogen-bonded complexes is larger in EtOH than in MeOH. 53 Conversely, the increase in e-density on the imidazole nitrogen promotes the hydrogen bonding between the H-donor BTC and the H-acceptor 2-EIM by transfer of a proton. This interaction contributes additional stability to the complex that is formed.…”
A new complex formed by the transfer of charge between 2-ethylimidazole (2-EIM) as an electron donor and 1,2,4,5-benzenetetracarboxylic acid (BTC) as an π acceptor has been created and studied using...
“…According to Kamlet–Taft parameters, it is conceivable that the formation constant for hydrogen-bonded complexes is larger in EtOH than in MeOH. 53 Conversely, the increase in e-density on the imidazole nitrogen promotes the hydrogen bonding between the H-donor BTC and the H-acceptor 2-EIM by transfer of a proton. This interaction contributes additional stability to the complex that is formed.…”
A new complex formed by the transfer of charge between 2-ethylimidazole (2-EIM) as an electron donor and 1,2,4,5-benzenetetracarboxylic acid (BTC) as an π acceptor has been created and studied using...
“…The energy barrier to the phenyl-imide N–C bond rotation, especially of phenyl rings with an ortho -substituted methyl, tends to be sufficiently high such that equilibrating conformers interconvert slowly on the NMR timescale. 13,14 The test models consist of an N -phenylimide integrated into a polyether macrocycle—henceforth labelled as “macrobalances” for convenience—where two distinct low-energy conformers are observed. The ortho -methyl of the folded conformer is positioned directly above the π-electron cloud of the adjacent aromatic ring, leading to an intramolecular methyl CH–π interaction (Fig.…”
Incorporating an N-phenylimide unit into macrocycles enabled measurements of macrocyclization strains by comparing the N-phenylimide’s conformational changes to similar units attached to a linear-chain control. Systems of larger macrocycles displayed...
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