An NMR investigation of the importance of intramolecular hydrogen bonding in determining the conformational equilibrium of ethylene glycol in solution

2005 ◽  
Vol 43 (3) ◽  
pp. 225-230 ◽  
Author(s):  
Krag A. Petterson ◽  
Robin S. Stein ◽  
Michael D. Drake ◽  
John D. Roberts
Keyword(s):  
Hydrogen Bonding ◽  
Ethylene Glycol ◽  
Conformational Equilibrium ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Hydrogen

scholarly journals Conformational analysis and intramolecular interactions in monosubstituted phenylboranes and phenylboronic acids

2013 ◽  
Vol 9 ◽  
pp. 1127-1134 ◽  
Author(s):  
Josué M Silla ◽  
Rodrigo A Cormanich ◽  
Roberto Rittner ◽  
Matheus P Freitas
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Conformational Analysis ◽  
Conformational Equilibrium ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Interactions ◽  
Coupling Constant ◽  
Intramolecular Hydrogen ◽  
Phenylboronic Acids ◽  
Electron Donation

A 1 TS J F,H(O) coupling pathway, dictated by a hydrogen bond, in some 2-fluorobenzoic acids has been observed, while such an interaction does not occur in 2-fluorophenol. Thus, this work reports the conformational analysis of 2-fluorophenylboronic acid (1), in order to evaluate a possible intramolecular OH∙∙∙F hydrogen bond in comparison to an nF→pB interaction, which mimics the quantum nF→σ*OH hydrogen bond that would be expected in 2-fluorophenol. 2-Fluorophenylborane (3), which does not experience hydrogen bonding, was used to verify whether nF→pB interaction governs the conformational equilibrium in 1 due to a predominant OH∙∙∙F hydrogen bond or to other effects. A series of 2-X-phenylboranes (X = Cl, Br, NH2, PH2, OH and SH) were further computationally analyzed to search for electron donors to boron, capable of influencing the conformational equilibrium. Overall, the intramolecular OH∙∙∙F hydrogen bond in 1 is quite stabilizing and dictates the 1 h J F,H(O) coupling constant. Moreover, electron donation to the empty p orbital of boron (for noncoplanar BH2 moiety relative to the phenyl ring) is also significantly stabilizing for the NH2 and PH2 derivatives, but not enough to make the corresponding conformers appreciably populated, because of steric effects and the loss of πCC→pB resonance. Thus, the results found earlier for 2-fluorophenol about the lack of intramolecular hydrogen bonding are now corroborated.

Microwave Spectrum, Intramolecular Hydrogen Bonding and Conformational Equilibrium of trans-2-Methylcyclopropanemethanol.

1992 ◽  
Vol 46 ◽  
pp. 861-866 ◽  
Author(s):  
K.-M. Marstokk ◽  
Harald Møllendal ◽  
Sine Larsen ◽  
Carsten H. Petersen ◽  
Johan Springborg ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Conformational Equilibrium ◽  
Intramolecular Hydrogen Bonding ◽  
Microwave Spectrum ◽  
Intramolecular Hydrogen

An FT-IR study on intramolecular hydrogen-bonding in ethylene glycol derivatives

1991 ◽  
Vol 245 (3-4) ◽  
pp. 183-194 ◽  
Author(s):  
F.A.J. Singelenberg ◽  
J.H. van der Maas ◽  
L.M.J. Kroon-Batenburg
Keyword(s):  
Hydrogen Bonding ◽  
Ethylene Glycol ◽  
Intramolecular Hydrogen Bonding ◽  
Ft Ir ◽  
Ethylene Glycol Derivatives ◽  
Ir Study ◽  
Intramolecular Hydrogen

scholarly journals Microwave Spectrum, Conformation, Intramolecular Hydrogen Bonding and Ab Initio Calculations for Ethylene Glycol Vinyl Ether.

1995 ◽  
Vol 49 ◽  
pp. 728-733 ◽  
Author(s):  
K.-M. Marstokk ◽  
Harald Møllendal ◽  
I. F. Heglund ◽  
R. Sande ◽  
C. P. Tønseth ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Ethylene Glycol ◽  
Ab Initio Calculations ◽  
Ab Initio ◽  
Vinyl Ether ◽  
Intramolecular Hydrogen Bonding ◽  
Microwave Spectrum ◽  
Intramolecular Hydrogen

scholarly journals Microwave Spectrum, Conformational Equilibrium, Intramolecular Hydrogen Bonding and Centrifugal Distortion of 3-Aminopropionitrile.

1983 ◽  
Vol 37a ◽  
pp. 493-501 ◽  
Author(s):  
Ole-Anders Braathen ◽  
K.-M. Marstokk ◽  
Harald Møllendal ◽  
H. Priebe ◽  
D. L. Powell ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Conformational Equilibrium ◽  
Intramolecular Hydrogen Bonding ◽  
Microwave Spectrum ◽  
Centrifugal Distortion ◽  
Intramolecular Hydrogen
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