Hydrogen bonded arrays: The power of multiple hydrogen bonds

Alireza Shokri, Jacob Schmidt, Xue Bin Wang, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

56 Scopus citations

Abstract

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 (HOCH 2CH 2) 2CHO -(2a), (HOCH 2CH 2) 3CO - (3a), and (HOCH 2CH 2CH(OH)CH 2) 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 three hydrogen bonds but also can increase the interaction energy between noncharged OH groups by 5.8 kcal mol -1 or more per hydrogen bond. This can lead to pK a values that are very different from those in water and can provide some of the impetus for catalytic processes.

Original languageEnglish (US)
Pages (from-to)2094-2099
Number of pages6
JournalJournal of the American Chemical Society
Volume134
Issue number4
DOIs
StatePublished - Feb 1 2012

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