Intramolecular interactions I. The use of someMannich bases of naphthols as model compounds for intramolecular hydrogen bonding

1980 ◽  
Vol 111 (3) ◽  
pp. 563-574 ◽  
Author(s):  
Ernst Haslinger ◽  
Peter Wolschann
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Interactions ◽  
Model Compounds ◽  
Intramolecular Hydrogen

Seven-Membered Intramolecular Hydrogen Bonding of Phenols: Database Analysis and Phloroglucinol Model Compounds

2012 ◽  
Vol 2012 (24) ◽  
pp. 4483-4492 ◽  
Author(s):  
Ronald K. Castellano ◽  
Yan Li ◽  
Edwin A. Homan ◽  
Andrew J. Lampkins ◽  
Iris V. Marín ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Model Compounds ◽  
Database Analysis ◽  
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.

Intramolecular hydrogen bonding stabilizes the nuclearity of complexes. A comparative study based on the H-carborane and Me-carborane framework

2015 ◽  
Vol 44 (22) ◽  
pp. 10399-10409 ◽  
Author(s):  
Mònica Fontanet ◽  
Montserrat Rodríguez ◽  
Xavier Fontrodona ◽  
Isabel Romero ◽  
Clara Viñas ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Comparative Study ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Interactions ◽  
Intramolecular Hydrogen

The H– on the adjacent carbon of the carboranylcarboxylate ligand is responsible for intramolecular interactions that stabilize the nuclearity of Cu(ii) complexes.

Vapour phase infrared studies of alcohols - I. Intramolecular interactions and self-association

1973 ◽  
Vol 335 (1600) ◽  
pp. 97-111 ◽  
Keyword(s):  
Hydrogen Bonding ◽  
Infrared Spectra ◽  
Path Length ◽  
Intramolecular Hydrogen Bonding ◽  
Vapour Phase ◽  
Intramolecular Interactions ◽  
Argon Matrix ◽  
Infrared Studies ◽  
Self Association ◽  
Intramolecular Hydrogen

Infrared spectra are reported of methanol, ethanol, propan-2-ol, 2-methylpropan-2-ol, 2, 2, 2-trifluoroethanol, 2, 2, 3, 3-tetrafluoropropan-1-ol and 1, 1, 1, 3, 3, 3-hexafluoropropan-2-ol in the vapour phase in a 1 m path-length cell at pressures up to the s. v. p. of the alcohol. Also reported are 40 m path-length vapour and argon matrix spectra of trifluoroethanol. Dimer absorptions are identified for all the alkanols and for trifluoroethanol, and some estimates of ∆ H provided. Trifluoroethanol exhibits a striking series of sum-and-difference bands of the OH stretch with other fundamentals, 14 summation modes being observed extending in frequency to over 5000 cm -1 and involving most of the fundamentals below 1500 cm -1 . Other fluoroalcohols with fluorines substituted on β carbon atoms exhibit similar sum-and-difference modes. The alkanols exhibit only one such pair of bands due to the OH stretch plus or minus the OH torsion, and this provides a convenient method of measuring the torsional frequencies. The different behaviour of the fluoroalcohols is attributed to intramolecular hydrogen bonding.

Sign in / Sign up

Export Citation Format

Share Document