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Hydration of trimethylamine-N-oxide and of dimethyldodecylamine-N-oxide: An ab initio study

Kocherbitov, Vitaly LU ; Veryazov, Valera LU and Söderman, Olle LU (2007) In Journal of molecular structure. Theochem 808(1-3). p.111-118
Abstract
Density functional theory (B3LYP) calculations of the hydration of trimethylamine-N-oxide (TMAO) and a surfactant dimethyldodecylamine-N-oxide (DDAO) are reported. Hydrogen-bonded complexes of DDAO with up to three water molecules and of TMAO with up to five water molecules are studied. Interactions of both TMAO and DDAO with water give rise to the binding energies that are much higher than that in the water dimer. A significant charge transfer from amine oxide to water is observed. Energies of water-water interactions increase in the presence of amine oxides. The hydration number of TMAO in the hydrogen bonded complexes is shown to be three. The energies of amine oxide-water interactions in the hydrogen bonded complexes have been analyzed... (More)
Density functional theory (B3LYP) calculations of the hydration of trimethylamine-N-oxide (TMAO) and a surfactant dimethyldodecylamine-N-oxide (DDAO) are reported. Hydrogen-bonded complexes of DDAO with up to three water molecules and of TMAO with up to five water molecules are studied. Interactions of both TMAO and DDAO with water give rise to the binding energies that are much higher than that in the water dimer. A significant charge transfer from amine oxide to water is observed. Energies of water-water interactions increase in the presence of amine oxides. The hydration number of TMAO in the hydrogen bonded complexes is shown to be three. The energies of amine oxide-water interactions in the hydrogen bonded complexes have been analyzed using differential energetic parameters analogous to the parameters measured in calorimetric experiments. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
MOLECULAR-DYNAMICS SIMULATION, hydrogen bond, water, DFT, SOLUTES, DDAO, TMAO, D-GLUCOSIDE/WATER SYSTEM, CRYSTAL-STRUCTURE, PHASE-DIAGRAM
in
Journal of molecular structure. Theochem
volume
808
issue
1-3
pages
111 - 118
publisher
Elsevier
external identifiers
  • wos:000246334000014
  • scopus:33947702059
ISSN
0166-1280
DOI
10.1016/j.theochem.2006.12.043
language
English
LU publication?
yes
id
3ae091c0-5764-4800-a8bf-0e20a52df916 (old id 1026560)
date added to LUP
2008-02-06 18:09:14
date last changed
2017-08-06 04:34:57
@article{3ae091c0-5764-4800-a8bf-0e20a52df916,
  abstract     = {Density functional theory (B3LYP) calculations of the hydration of trimethylamine-N-oxide (TMAO) and a surfactant dimethyldodecylamine-N-oxide (DDAO) are reported. Hydrogen-bonded complexes of DDAO with up to three water molecules and of TMAO with up to five water molecules are studied. Interactions of both TMAO and DDAO with water give rise to the binding energies that are much higher than that in the water dimer. A significant charge transfer from amine oxide to water is observed. Energies of water-water interactions increase in the presence of amine oxides. The hydration number of TMAO in the hydrogen bonded complexes is shown to be three. The energies of amine oxide-water interactions in the hydrogen bonded complexes have been analyzed using differential energetic parameters analogous to the parameters measured in calorimetric experiments.},
  author       = {Kocherbitov, Vitaly and Veryazov, Valera and Söderman, Olle},
  issn         = {0166-1280},
  keyword      = {MOLECULAR-DYNAMICS SIMULATION,hydrogen bond,water,DFT,SOLUTES,DDAO,TMAO,D-GLUCOSIDE/WATER SYSTEM,CRYSTAL-STRUCTURE,PHASE-DIAGRAM},
  language     = {eng},
  number       = {1-3},
  pages        = {111--118},
  publisher    = {Elsevier},
  series       = {Journal of molecular structure. Theochem},
  title        = {Hydration of trimethylamine-N-oxide and of dimethyldodecylamine-N-oxide: An ab initio study},
  url          = {http://dx.doi.org/10.1016/j.theochem.2006.12.043},
  volume       = {808},
  year         = {2007},
}