Hydrogen Bonded Arrays: The Power of Multiple Hydrogen Bonds

Journal Article · Wed Feb 01 04:00:00 EST 2012 · Journal of the American Chemical Society, 134(4):2094-2099

DOI:https://doi.org/10.1021/ja2081907· OSTI ID:1038368

Shokri, Alireza; Schmidt, Jacob C.; Wang, Xue B.; Kass, Steven R.

Hydrogen bond interactions in small covalent model compounds (i.e. deprotonated polyhydroxy alcohols) were measured by negative ion photoelectron spectroscopy. The experimentally determined vertical and adiabatic electron detachment energies for (HOCH2CH2)2CHO (2a), (HOCH2CH2) 3CO (3a) and (HOCH2CH2CH(OH)CH2)3CO (4a) reveal that hydrogen-bonded networks can provide enormous stabilizations, and that a single charge center not only can be stabilized by up to 3 hydrogen bonds but it can increase the interaction energy between non-charged OH groups by 5.8 kcal mol1 or more per hydrogen bond. This can lead to pKa values that are very different than in water, and provide some of the impetus for catalytic processes.

• Research Organization: Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC05-76RL01830
• OSTI ID: 1038368
• Report Number(s): PNNL-SA-82915; 42309; 42590; KC0301020
• Journal Information: Journal of the American Chemical Society, 134(4):2094-2099, Journal Name: Journal of the American Chemical Society, 134(4):2094-2099 Journal Issue: 4 Vol. 134; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

08 HYDROGEN
ALCOHOLS
ANIONS
ELECTRON DETACHMENT
Environmental Molecular Sciences Laboratory
HYDROGEN
PHOTOELECTRON SPECTROSCOPY