scholarly journals α-Fluoro-o-cresols: The Key Role of Intramolecular Hydrogen Bonding in Conformational Preference and Hydrogen-Bond Acidity

ChemPhysChem ◽  
2016 ◽  
Vol 17 (17) ◽  
pp. 2702-2709 ◽  
Author(s):  
Elena Bogdan ◽  
Alexis Quarré de Verneuil ◽  
François Besseau ◽  
Guillaume Compain ◽  
Bruno Linclau ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Conformational Preference ◽  
Hydrogen Bond Acidity ◽  
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.

Computer aided design of organic superbases: the role of intramolecular hydrogen bonding

2002 ◽  
Vol 26 (10) ◽  
pp. 1329-1334 ◽  
Author(s):  
Borislav Kovačević ◽  
Zvonimir B. Maksić ◽  
Robert Vianello ◽  
Miljenko Primorac
Keyword(s):  
Hydrogen Bonding ◽  
Computer Aided Design ◽  
Intramolecular Hydrogen Bonding ◽  
Computer Aided ◽  
Intramolecular Hydrogen ◽  
Aided Design

Antioxidant Activity ofo-Bisphenols:  the Role of Intramolecular Hydrogen Bonding

2003 ◽  
Vol 68 (13) ◽  
pp. 5198-5204 ◽  
Author(s):  
Riccardo Amorati ◽  
Marco Lucarini ◽  
Veronica Mugnaini ◽  
Gian Franco Pedulli
Keyword(s):  
Antioxidant Activity ◽  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Hydrogen

scholarly journals Towards Understanding Photodegradation Pathways in Lignins: The Role of Intramolecular Hydrogen Bonding in Excited States

2014 ◽  
Vol 5 (12) ◽  
pp. 2138-2143 ◽  
Author(s):  
Jamie D. Young ◽  
Michael Staniforth ◽  
Jacob C. Dean ◽  
Gareth M. Roberts ◽  
Federico Mazzoni ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Excited States ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Hydrogen

The stabilizing role of intramolecular hydrogen bonding in disubstituted hydroxy-quinones

2013 ◽  
Vol 110 ◽  
pp. 628-633 ◽  
Author(s):  
Georgina Armendáriz-Vidales ◽  
Eduardo Martínez-González ◽  
Héctor Javier Cuevas-Fernández ◽  
Didier Omar Fernández-Campos ◽  
Rutely C. Burgos-Castillo ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Hydrogen
Sign in / Sign up

Export Citation Format

Share Document