Ab initio analysis of 2-aminoethanol conformers, including electron correlation corrections for the energy

Vanquickenborne, L. G.; Coussens, Betty; Verlinde, Christophe L. M. J.; Ranter, Camiel De

doi:10.1016/0166-1280(89)87058-7

Cited by 24 publications

(25 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The stability of this conformer was attributed to the presence of an intramolecular hydrogen bond of the type OH…N, that has also been found to operate in other similar molecules [20,21]. This result has received support from theoretical calculations carried out at different levels of approximation [3][4][5][6][7][8][9][10][11][12][13][14][15]. However, different methods of calculation do not fully agree with respect to the relative order of stability of the remaining conformers, despite some general consensus has emerged from the whole set of calculations already carried out: (a) conformers where OH…N or NH…O intramolecular hydrogen bonding operate have an increased stability (the estimated stabilizing energies for the stronger intramolecular H-bonding of each type-OH…N, in g H Gg H , and NH…O in gGt -amount to ca.…”

Section: Introductionsupporting

confidence: 53%

“…Conformational isomerism in AE has been the subject of several theoretical and experimental studies [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. For the isolated molecule situation and in the gaseous phase, it has been shown that intramolecular hydrogen bonding plays a decisive role in stabilizing those conformations which correspond to the most stable conformational states of the studied molecule [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A concerted SCF-MO ab initio and vibrational spectroscopic study of the conformational isomerism in 2-aminoethanol

Silva

Duarte

Fausto

1999

Journal of Molecular Structure

View full text Add to dashboard Cite

Conformational isomerism in isolated and liquid 2-aminoethanol was investigated by a concerted molecular orbital and vibrational spectroscopic approach. The molecular structures, relative energies, dipole moments and vibrational spectra (both infrared and Raman) of the various possible conformers of the studied compound were calculated, using the extended 6-31G* basis set at the HF-SCF ab initio level of theory. The theoretical results were then used to interpret infrared and Raman data obtained under different experimental conditions. It was found that none of the most populated conformational states existing in the pure liquid (where intermolecular H-bonding occurs extensively)-the gGt and tTt conformers-, correspond to the conformational ground state for the isolated 2-aminoethanol molecule-the intramolecularly H-bonded g H Gg H conformer.

show abstract

Section: Introductionsupporting

confidence: 53%

Section: Introductionmentioning

confidence: 99%

A concerted SCF-MO ab initio and vibrational spectroscopic study of the conformational isomerism in 2-aminoethanol

Silva

Duarte

Fausto

1999

Journal of Molecular Structure

View full text Add to dashboard Cite

show abstract

“…For molecules of monoethanolamine (MEA), 14 nonequivalent conformers have been established, 13 of which are stable [1,6,[12][13][14][15]. As with ethylene glycol, some of the conformers are stabilized with intramolecular hydrogen bonds [1,6,[12][13][14][15][16]18].…”

Section: Introductionmentioning

confidence: 99%

“…As with ethylene glycol, some of the conformers are stabilized with intramolecular hydrogen bonds [1,6,[12][13][14][15][16]18]. Considerably fewer works have been devoted to inter molecular hydrogen bonds [14,16], and just one work used the NBO (Natural Bond Orbital) approach [14].…”

Section: Introductionmentioning

confidence: 99%

Intra- and intermolecular hydrogen bonds in ethylene glycol, monoethanolamine, and ethylenediamine

Krest’yaninov

Titova

Zaichikov

2014

Russ. J. Phys. Chem.

View full text Add to dashboard Cite

The structures of ethylene glycol, aminoethanol, ethylenediamine, and their dimers with the for mation of hydrogen bonds of different types are optimized by density functional theory (DFT) using hybrid functional B3LYP in the basis of 6 31++G(d,p), 6 311++G(2d,2p) and aug CC pVTZ. Energies of interac tions, hydrogen bond parameters, and oscillation frequency are calculated, and NBO analysis is performed. The types of hydrogen bonds formed in dimers of 1,2 disubstituted ethanes X-CH 2 -CH 2 -Y (X, Y = OH, NH 2 ) are established. Keywords: ethylene glycol, aminoethanol, ethylenediamine, intro and intermolecular hydrogen bonds, quan tum chemical methods of calculation.

show abstract

“…Theoretical studies based on ab initio calculations, on either isolated alkanolamines or dimers, probed the conformational features and the characteristics of the intramolecular hydrogen bonds. [8][9][10][11][12][13][14][15][16][17][18][19] Theoretical methodology had also been used to determine thermodynamic properties. Da Silva and Svendsen [20] combined ab initio methods and Monte Carlo free-energy perturbations to predict protonation constant (pK a ) values for several amines.…”

Section: Introductionmentioning

confidence: 99%

Molecular Simulations of Primary Alkanolamines Using an Extendable Force Field

et al. 2012

View full text Add to dashboard Cite

A classical force field is proposed for the molecular simulation of primary alkanolamines containing a NH(2)-C-C-OH backbone. A method is devised to take into account the polar (H-bonding) environment of the alkanolamines by calculating electrostatic charges in the presence of explicit solvent molecules. The force field does not use a universal set of charges, but is rather constructed by following a general method for obtaining specific charges for the different alkanolamines. The model is parameterized on the two simplest primary alkanolamines and then validated by calculating thermodynamic properties of five other molecules. Experimental liquid densities and enthalpies of vaporization are also reported in order to complete existing literature data. The predicted ability of the force field is evaluated by comparing the simulation results with experimental densities and enthalpies of vaporization. Densities are predicted with an uncertainty of 1.5 % and enthalpies of vaporization with an uncertainty of 1 kJ mol(-1). A decomposition of the interaction energy into electrostatic and repulsive-dispersive interactions and an analysis of hydrogen-bond statistics lead to a complex picture. Some terms of these interactions are related to the molecular structure in a clear way, others are not. The results provide insights into the structure-property relations that contribute to a better description of the thermodynamic properties of alkanolamines.

show abstract

Ab initio analysis of 2-aminoethanol conformers, including electron correlation corrections for the energy

Cited by 24 publications

References 32 publications

A concerted SCF-MO ab initio and vibrational spectroscopic study of the conformational isomerism in 2-aminoethanol

A concerted SCF-MO ab initio and vibrational spectroscopic study of the conformational isomerism in 2-aminoethanol

Intra- and intermolecular hydrogen bonds in ethylene glycol, monoethanolamine, and ethylenediamine

Molecular Simulations of Primary Alkanolamines Using an Extendable Force Field

Contact Info

Product

Resources

About