Electron Donation in the Water-Water Hydrogen Bond

2008 ◽  
Vol 15 (4) ◽  
pp. 851-855 ◽  
Author(s):  
Rustam Z. Khaliullin ◽  
Alexis T. Bell ◽  
Martin Head-Gordon
Keyword(s):  
Hydrogen Bond ◽  
Electron Donation ◽  
Water 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.

Hydration of phospholipid interface: carbonyl–water hydrogen bond association

2009 ◽  
Vol 11 (43) ◽  
pp. 9979 ◽  
Author(s):  
Victor Volkov ◽  
Yuji Takaoka ◽  
Roberto Righini
Keyword(s):  
Hydrogen Bond ◽  
Water Hydrogen

scholarly journals Reactions and interactions between peri-groups in 1-dimethylamino-naphthalene salts: an example of a “through space” amide

2016 ◽  
Vol 88 (4) ◽  
pp. 317-331
Author(s):  
Amélie Wannebroucq ◽  
Andrew P. Jarmyn ◽  
Mateusz B. Pitak ◽  
Simon J. Coles ◽  
John D. Wallis
Keyword(s):  
Hydrogen Bond ◽  
Methyl Ester ◽  
Carbonyl Group ◽  
Dimethylamino Group ◽  
X Ray ◽  
X Ray Crystallography ◽  
Electron Donation ◽  
Protonated Cation

Abstract8-Dimethylaminonaphthalene-1-carbaldehyde reacts readily at 0°C with benzoyl or pivaloyl chloride by O-acylation and formation of a N–C bond (1.566(2)–1.568(3) Å) between the peri-substituents to give a salt. The reaction is promoted by electron donation from the dimethylamino group to the carbonyl group, akin to the properties of an amide. In contrast, the corresponding methyl ester and N,N-diisopropylamide react with acid in ether by protonation of the dimethylamino group and formation of a hydrogen bond to the carbonyl group, while under similar conditions the N,N-dimethylamide undergoes ready hydrolysis to the acid. The structures of products are determined by X-ray crystallography, and from the latter hydrolysis crystals containing zwitterionic 1-dimethylammonium-naphthalene-8-carboxylate and the corresponding O-protonated cation along with dimethylammonium and triflate ions were obtained.

Understanding the effect of nanoconfinement on the structure of water hydrogen bond networks

2019 ◽  
Vol 21 (47) ◽  
pp. 26237-26250 ◽  
Author(s):  
Myong In Oh ◽  
Mayuri Gupta ◽  
Chang In Oh ◽  
Donald F. Weaver
Keyword(s):  
Hydrogen Bond ◽  
Information Flow ◽  
Flow Model ◽  
Phospholipid Membranes ◽  
Structure Of Water ◽  
Hydrogen Bond Networks ◽  
Information Flow Model ◽  
Water Hydrogen

Dynamic hydrogen bond trails in water confined between two phospholipid membranes traced by the information flow model.

Water dynamics at electrified graphene interfaces: a jump model perspective

2020 ◽  
Vol 22 (19) ◽  
pp. 10581-10591 ◽  
Author(s):  
Yiwei Zhang ◽  
Guillaume Stirnemann ◽  
James T. Hynes ◽  
Damien Laage
Keyword(s):  
Hydrogen Bond ◽  
Electrode Potential ◽  
Water Dynamics ◽  
Asymmetric Behavior ◽  
Jump Model ◽  
Reorientation Dynamics ◽  
Potential Sign ◽  
Water Hydrogen

Changes in water reorientation dynamics at electrified graphene interfaces arise from the interfaces’ impact on water hydrogen-bond exchanges; the asymmetric behavior with electrode potential sign is quantitatively described by an extended jump model.

Water hydrogen bond analysis on hydrophilic and hydrophobic biomolecule sites

2008 ◽  
Vol 10 (32) ◽  
pp. 4968 ◽  
Author(s):  
Daniela Russo ◽  
Jacques Ollivier ◽  
José Teixeira
Keyword(s):  
Hydrogen Bond ◽  
Water Hydrogen ◽  
Hydrogen Bond Analysis
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