Nature of intramolecular interactions of vitamin C in view of interacting quantum atoms: the role of hydrogen bond cooperativity on geometry

2016 ◽  
Vol 18 (27) ◽  
pp. 18278-18288 ◽  
Author(s):  
Saeid Ebrahimi ◽  
Hossein A. Dabbagh ◽  
Kiamars Eskandari
Keyword(s):  
Hydrogen Bond ◽  
Vitamin C ◽  
Interatomic Interaction ◽  
Cooperative Networks ◽  
Intramolecular Interactions ◽  
Interaction Energies ◽  
Interacting Quantum Atoms ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bond Cooperativity

For the intramolecular hydrogen bond interplay in cooperativity, changes of the IQA atomic and interatomic interaction energies of the participant interactions were monitored during the formation of cooperative networks.

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.

Role of the bifurcated intramolecular hydrogen bond on the physico-chemical profile of the novel azo pyridone dyes

2019 ◽  
Vol 162 ◽  
pp. 562-572 ◽  
Author(s):  
Jelena Lađarević ◽  
Bojan Božić ◽  
Luka Matović ◽  
Biljana Božić Nedeljković ◽  
Dušan Mijin
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
The Novel ◽  
Chemical Profile ◽  
Physico Chemical ◽  
Intramolecular Hydrogen

The Antimalarial Ferroquine: Role of the Metal and Intramolecular Hydrogen Bond in Activity and Resistance

2011 ◽  
Vol 6 (3) ◽  
pp. 275-287 ◽  
Author(s):  
Faustine Dubar ◽  
Timothy J. Egan ◽  
Bruno Pradines ◽  
David Kuter ◽  
Kanyile K. Ncokazi ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Intramolecular Hydrogen

Correlating experimental electrochemistry and theoretical calculations in 2′-hydroxy chalcones: the role of the intramolecular hydrogen bond

RSC Advances ◽  
2015 ◽  
Vol 5 (63) ◽  
pp. 50929-50937 ◽  
Author(s):  
Maximiliano Martínez-Cifuentes ◽  
Ricardo Salazar ◽  
Carlos A. Escobar ◽  
Boris E. Weiss-López ◽  
Leonardo S. Santos ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Theoretical Calculations ◽  
Electrochemical Behaviour ◽  
Redox Properties ◽  
Methoxy Substituent ◽  
Intramolecular Hydrogen

The molecular structure and electrochemical behaviour of a series of 2′-hydroxychalcones were studied. Results show the importance of the intramolecular hydrogen bond and the methoxy substituent pattern on the redox properties of these compounds.

A DFT-D study on the stability and intramolecular interactions of the energetic salts of 3,6-dihydrazido-1,2,4,5-tetrazine

2016 ◽  
Vol 94 (1) ◽  
pp. 28-34
Author(s):  
Xueli Zhang ◽  
Xuedong Gong
Keyword(s):  
Hydrogen Bond ◽  
Density Functional ◽  
Lattice Energy ◽  
Intramolecular Interactions ◽  
Bond Energies ◽  
Dispersion Energy ◽  
Linear Relationships ◽  
The Stability ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bond Energies

Structures of the salts I–IV formed by 3,6-dihydrazido-1,2,4,5-tetrazine with HNO3, HN(NO2)2, HClO4, and HC(NO2)3, respectively, were studied using dispersion-corrected density functional theory. The intramolecular hydrogen bond energies of I–IV were estimated using the quantum theory of atoms in molecules. The total hydrogen bond energies (EH,tot) have the order of I (65.60 kcal/mol) > II (46.24 kcal/mol) > III (39.13 kcal/mol) > IV (19.68 kcal/mol). In addition, the charge transfer (q), binding energy (Eb), lattice energy (HL), dispersion energy (Edis), and second-order perturbation energy (E2) were evaluated for studying the intramolecular interactions between the cation and anion. Linear relationships exist between any two of EH,tot, qtot, Eb, and E2,tot. HLs have the same variation trend as h50s (characteristic height) and may be used as the indicator of impact sensitivity. The HOMOs and LUMOs of I–IV are derived from the HOMOs of the isolated anions and the LUMOs of the isolated cations, respectively. Ultraviolet spectra of I–IV have the strongest absorptions at around 442, 445, 427, and 587 nm, respectively. The excitations HOMO→LUMO to HOMO–7→LUMO play important roles in the first three excited states.

scholarly journals En route to phosphonato iridium(i) complexes: the decisive effect of an intramolecular hydrogen bond

2016 ◽  
Vol 45 (3) ◽  
pp. 951-962
Author(s):  
Vincenzo Passarelli ◽  
Jesús J. Pérez-Torrente ◽  
Luis A. Oro
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Decisive Role ◽  
Decisive Effect ◽  
Intramolecular Hydrogen

The decisive role of an intramolecular NH⋯OP hydrogen bond in the formation of a dimethyl phosphonato iridium(i) complex is shown.

The role of aromatic rings as hydrogen-bond acceptors in molecular recognition

1993 ◽  
Vol 345 (1674) ◽  
pp. 105-112 ◽  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Gas Phase ◽  
Signal Transmission ◽  
Aromatic Rings ◽  
Aromatic Interactions ◽  
Proton Donors ◽  
The Stability ◽  
Intramolecular Hydrogen

Observations of phenol-benzene and ammonia—benzene complexes in the gas phase show that hydrogen bonds link their proton donors to the π electrons of the benzene with a bond energy of between 2 and 4 kcal mol -1 , large enough to be biologically significant. Intramolecular hydrogen bonds between OH and NH donors and aromatic acceptors have also been found in crystal structures of organic compounds. NH-aromatic interactions stabilize x-helices if donors and acceptors occur at successive turns of the helix. These interactions also contribute to the stability of several proteins and play an important part in cellular and synaptic signal transmission.

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