Hydrogen bond formation between aliphatic alcohols and tertiary amines

<b>Vibrational spectra of <i>t</i>-butyl alcohol, <i>t</i>-butylamine and <i>t</i>-butyl alcohol + <i>t</i>-butylamine binary liquid mixtures</b>

“…As the mole fraction of Bu t OH increases, this shoulder develops into a band centred at 3294 cm -1 indicating probably partially covalent linear hydrogen-bonded complex formation of the type NH 2 ----O-H. This band thus is due to the amine-alcohol complex which is in agreement with earlier reports [14,15]. Finally the 3294 cm -1 band dominates the spectrum at high concentrations of Bu t OH, leaving the other band as a shoulder.…”

Volumetric Properties of a Binary Mixture Composed of N,N-Dimethylcyclohexylamine and Alcohols

“…For example, the maximum negative values at 298.15 K are (−1.097, −1.094, −0.900, −1.033, −1.154, and −1.073) cm 3 ·mol –1 for ethanol + DMCA, n -propanol + DMCA, iso -propanol + DMCA, n -butanol + DMCA, iso -butanol + DMCA, and tert -butanol + DMCA system, respectively. With the addition of DMCA to a large volume of alcohol, molecular complexes may be formed due to the −OH···NR 3 – hydrogen bonding interaction between the unlike molecules. ,− Besides, the large differences of molar volume and steric structure between the alcohol molecule and DMCA molecule may also easily result in the geometrical accommodation. Hence, all these are possibly responsible to the volume shrinkage, which contributes to the overall negative V m E values.…”

“…Therefore, from this point, the n -butanol + DMCA mixture should exhibit the most negative V m E values. However, the real mixture containing small molecule ethanol deviates the ideality the most, which is in accordance with our reported work. ,,, This suggests that the accommodation of small alcohol molecules into the large structural space of DMCA is mainly responsible for the sequence of V m E values of linear alcohol + DMCA binary mixtures.…”

Stereodivergent, Diels–Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application

“…On the basis of previous studies of alcohol–amine complexes, 65 we envisaged a hydrogen-bonded complex between these amino Brønsted bases and the alcohol moiety of the dienes employed. We postulated that evidence for such an interaction might be detected by 13 C NMR through increased electron density at the carbinol-carbon of diene due to inductive effects propagated through the σ-framework.…”

“…Based on the aforementioned experimental and computational results suggesting that bulky Brønsted bases could not effectively compete with BTM as Lewis base promoter during the initial DA cycloaddition, we considered other roles that the Brønsted base could be serving during the cycloaddition. On the basis of previous studies of alcohol–amine complexes, 65 we envisaged a hydrogen-bonded complex between these amino Brønsted bases and the alcohol moiety of the dienes employed. We postulated that evidence for such an interaction might be detected by 13 C NMR through increased electron density at the carbinol-carbon of diene due to inductive effects propagated through the σ-framework.…”