31. Brinkley, Ray L.; Gupta, Ram B.  Hydrogen bonding with aromatic rings.    AIChE J.  (2001),  47(4),  948-953.


Thermodn. effects of hydrogen bonding are important in detg. the phase behavior in polar fluids.  While efforts to understand "strong" donor and "strong" acceptor combinations (H-bonds involving a formation energy more neg. than - 20 kJ/mol such as alkanol-alkanol H-bonding have been substantial, weak H-bonds involving double bonds or arom. rings as proton acceptors) have largely been ignored.  Using FTIR spectroscopy H-bonding between alc. donor and arom. ring-contg. acceptor mols. was studied including l-hexanol and cyclohexanol at low concns. where self-assocn. is negligible (strong donors).  H-bonding "weak" acceptors studied include toluene and m-xylene.  Clear spectroscopic evidence existed for the formation of H-bonds between the alc. and arom. mols., which are much weaker than conventional "strong donor"-"strong acceptor" H-bonds.  Using quant. FTIR measurements, the percentage of H-bonded alc. mols. over a range of arom. concns. was detd.  Ab initio calcns. also showed that alc.-arom. H-bonds are much weaker than alc.-alc. H-bonds.  This H-bonding, though weak, will contribute significantly to the chem. potential of the mols.


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