Hydrogen bonded arrays: The power of multiple hydrogen bonds

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

doi:10.1021/ja2081907

Hydrogen bonded arrays: The power of multiple hydrogen bonds

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

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63 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 language	English (US)
Pages (from-to)	2094-2099
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	134
Issue number	4
DOIs	https://doi.org/10.1021/ja2081907
State	Published - Feb 1 2012

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title = "Hydrogen bonded arrays: The power of multiple hydrogen bonds",

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.",

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T1 - Hydrogen bonded arrays

T2 - The power of multiple hydrogen bonds

AU - Shokri, Alireza

AU - Schmidt, Jacob

AU - Wang, Xue Bin

AU - Kass, Steven R.

PY - 2012/2/1

Y1 - 2012/2/1

N2 - 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.

AB - 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.

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Hydrogen bonded arrays: The power of multiple hydrogen bonds

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