Exploiting the Strong Hydrogen Bond Donor Properties of a Borinic Acid Functionality for Fluoride Anion Recognition

For almost 20 years, thioureas have been experiencing a renaissance of interest with the emerged development of asymmetric organocatalysts. Due to their relatively high acidity and strong hydrogen bond donor capability, they differ significantly from ureas and offer, appropriately modified, great potential as organocatalysts, chelators, drug candidates, etc. The review focuses on the family of chiral thioureas, presenting an overview of the current state of knowledge on their synthesis and selected applications in stereoselective synthesis and drug development.

Download Full-text

Linear solvation energy relationship. 46. An improved equation for correlation and prediction of octanol/water partition coefficients of organic nonelectrolytes (including strong hydrogen bond donor solutes)

The Journal of Physical Chemistry ◽

10.1021/j100329a035 ◽

1988 ◽

Vol 92 (18) ◽

pp. 5244-5255 ◽

Cited By ~ 341

Author(s):

Mortimer J. Kamlet ◽

Ruth M. Doherty ◽

Michael H. Abraham ◽

Yizhak Marcus ◽

Robert W. Taft

Keyword(s):

Hydrogen Bond ◽

Partition Coefficients ◽

Solvation Energy ◽

Strong Hydrogen Bond ◽

Hydrogen Bond Donor ◽

Linear Solvation Energy Relationship ◽

Linear Solvation Energy ◽

Linear Solvation

Download Full-text

Chain stopper engineering for hydrogen bonded supramolecular polymers

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.6.102 ◽

2010 ◽

Vol 6 ◽

pp. 869-875 ◽

Cited By ~ 8

Author(s):

Thomas Pinault ◽

Bruno Andrioletti ◽

Laurent Bouteiller

Keyword(s):

Hydrogen Bond ◽

Molar Mass ◽

Strong Hydrogen Bond ◽

Supramolecular Polymers ◽

Supramolecular Polymer ◽

Hydrogen Bond Donor ◽

Linear Chains ◽

Non Covalent Interactions ◽

Viscous Solutions ◽

Covalent Interactions

Supramolecular polymers are linear chains of low molar mass monomers held together by reversible and directional non-covalent interactions, which can form gels or highly viscous solutions if the self-assembled chains are sufficiently long and rigid. The viscosity of these solutions can be controlled by adding monofunctional compounds, which interact with the chain extremities: chain stoppers. We have synthesized new substituted ureas and thioureas and tested them as chain stoppers for a bis-urea based supramolecular polymer. In particular, the bis-thiourea analogue of the bis-urea monomer is shown not to form a supramolecular polymer, but a good chain stopper, because it is a strong hydrogen bond donor and a weak acceptor. Moreover, all substituted ureas tested reduce the viscosity of the supramolecular polymer solutions, but the best chain stopper is obtained when two hydrogen bond acceptors are placed in the same relative position as for the monomer and when no hydrogen bond donor is present.

Download Full-text

Interaction Behavior between Active Hydrogen Bond Donor-Acceptors as a Binding Decoration for Anion Recognition: Experimental Observation and Theoretical Validation

ChemistrySelect ◽

10.1002/slct.201602045 ◽

2017 ◽

Vol 2 (9) ◽

pp. 2815-2821 ◽

Cited By ~ 6

Author(s):

Monaj Karar ◽

Suvendu Paul ◽

Arabinda Mallick ◽

Tapas Majumdar

Keyword(s):

Hydrogen Bond ◽

Experimental Observation ◽

Anion Recognition ◽

Active Hydrogen ◽

Hydrogen Bond Donor ◽

Interaction Behavior

Download Full-text

Towards an understanding of the propensity for crystalline hydrate formation by molecular compounds

IUCrJ ◽

10.1107/s2052252516015633 ◽

2016 ◽

Vol 3 (6) ◽

pp. 430-439 ◽

Cited By ~ 25

Author(s):

Alankriti Bajpai ◽

Hayley S. Scott ◽

Tony Pham ◽

Kai-Jie Chen ◽

Brian Space ◽

...

Keyword(s):

Hydrogen Bond ◽

Crystal Packing ◽

Hydrate Formation ◽

Crystalline Hydrate ◽

Strong Hydrogen Bond ◽

Hydrogen Bond Donor ◽

Screening Experiments ◽

Group Form ◽

Structural Database ◽

Molecular Compounds

Hydrates are technologically important and ubiquitous yet they remain a poorly understood and understudied class of molecular crystals. In this work, we attempt to rationalize propensity towards hydrate formation through crystallization studies of molecules that lack strong hydrogen-bond donor groups. A Cambridge Structural Database (CSD) survey indicates that the statistical occurrence of hydrates in 124 molecules that contain five- and six-memberedN-heterocyclic aromatic moieties is 18.5%. However, hydrate screening experiments on a library of 11N-heterocyclic aromatic compounds with at least two acceptor moieties and no competing hydrogen-bond donors or acceptors reveals that over 70% of this group form hydrates, suggesting that extrapolation from CSD statistics might, at least in some cases, be deceiving. Slurrying in water and exposure to humidity were found to be the most effective discovery methods. Electrostatic potential maps and/or analysis of the crystal packing in anhydrate structures was used to rationalize why certain molecules did not readily form hydrates.

Download Full-text