The effect of intramolecular interactions on hydrogen bond acidityElectronic supplementary information (ESI) available: summary of retrained regression using DFT methods. See http://www.rsc.org/suppdata/ob/b3/b300598d/

Huque, Farah T.T.; Platts, James Alexis

doi:10.1039/b300598d

Cited by 44 publications

(21 citation statements)

References 30 publications

(16 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It also explains (Figure 1) why the introduction of a second fluorine atom into 1 (to give 7 ) leads to a decrease in H‐bond acidity (this new fluorine atom can engage in an intramolecular F⋅⋅⋅HO interaction), and why the introduction of an anti fluorine substituent into 2 (to also give 7 ) leads to a strong H‐bond acidity increase. The reduction of H‐bond acidity due to intramolecular H‐bonding had been reported previously for a series of phenols, and the energy of the intramolecular H‐bond was shown to be unrelated to the overall H‐bond acidity of the studied structures 34…”

Section: Methodssupporting

confidence: 75%

Cysteine‐Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding

Gac

Schwartz

Koepf

et al. 2010

Chemistry A European J

View full text Add to dashboard Cite

The straightforward syntheses of polyisocyanides containing the alanine-cysteine motif in their side chains have been achieved. Detailed characterization of the polymers revealed a well-defined and highly stable helical conformation of the polyimine backbone responsible for the formation of rodlike structures of over one hundred nanometers. The 4(1) helix is further stabilized by beta-sheet-like interactions between the peptide arms. As a result, the cysteine sulfur atoms are regularly aligned along the polymer axis, which provides a unique platform for the scaffolding of various entities by using versatile click-chemistry postmodification approaches. For instance, pyrene derivatives were introduced through thio-specific reactions involving either maleimide, iodoacetamide, or thioester groups, leading to arrays of stacked chromophores with excimer-like emission. A water-soluble cysteine-rich polyisocyanide was successfully biotinylated and coupled to streptavidin.

show abstract

Section: Methodssupporting

confidence: 75%

Cysteine‐Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding

Gac

Schwartz

Koepf

et al. 2010

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The structures of polypeptides and double helices of polynucleotides are directed by hydrogen bonding interactions. Their significant roles in solvation, diffusion through biological tissues of membranes, adsorption on to the surfaces are well recognized 7–9. The structures of α helix and β sheet of polynucleotides are directed by hydrogen bonding interactions 10.…”

Section: Introductionmentioning

confidence: 99%

Intra and intermolecular hydrogen bonding in formohydroxamic acid

Kaur

Kohli

2007

Int J of Quantum Chemistry

View full text Add to dashboard Cite

ABSTRACT:The presence of hydrogen bonding interactions in several tautomeric forms of formohydroxamic acid (FHA) and 1:1 association among the tautomeric forms and water-coordinated tautomeric forms of FHA is explored theoretically. Out of the seven equilibrium structures, four tautomeric forms have been selected for aggregation with single water molecule and dimer formation. Fifteen aggregates of FHA with H 2 O have been optimized at MP2/AUG-cc-PVDZ level and analyzed for intramolecular and intermolecular H-bond interactions. Twenty-seven dimers of the four tautomeric forms have been obtained at MP2/6-31ϩG* level. The stabilization energies associated with dimerization and adduct formation with water are the result of H-bond interactions and range from very weak to medium. The atomic charges and NBO analysis indicate that the electrostatic and the charge transfer are the important components favoring H-bond formation.

show abstract

“…Selected Molecular, Supramolecular, and Crystal Parameters for Racemic and/or Enantiopure Non-Carborane Based 2-Pyridylalcohols from the CSD36 …”

mentioning

confidence: 99%

Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

Tsang

Salvo

Teixidor

et al. 2015

Crystal Growth & Design

View full text Add to dashboard Cite

International audienceTen structurally related racemic 2-pyridylmethyl alcohols containing an o-carborane core (1,2-closo-C2B10H10; rac-1a) or m-carborane (1,7-closo-C2B10H10; rac-2a) or p-carborane (1,7-closo-C2B10H10; rac-3a) and their enantiopure forms (R- and S-1a or R- and S-2a or R- and S-3a), as well as an iodo derivative of rac-3a (rac-4a) and a non-carborane derivative (C6H5; rac-5) have been studied by single crystal X-ray crystallography. All racemic and enantiopure structures show O-H center dot center dot center dot N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O-H center dot center dot center dot N hydrogen bonded trimers. A comparison of these X-ray structures with that for others found in the Cambridge Structural Database for chiral 2-pyridyl alcohols-either in racemic or enantiopure forms-that form O-H center dot center dot center dot N hydrogen bonded homochiral 21-helical networks reveals a possible relationship between the torsion angle of the hydrogen bond donor and acceptor groups in these molecules and the hydrogen bonded supramolecular helices formed in the solid state

show abstract

The effect of intramolecular interactions on hydrogen bond acidityElectronic supplementary information (ESI) available: summary of retrained regression using DFT methods. See http://www.rsc.org/suppdata/ob/b3/b300598d/

Cited by 44 publications

References 30 publications

Cysteine‐Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding

Cysteine‐Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding

Intra and intermolecular hydrogen bonding in formohydroxamic acid

Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

Contact Info

Product

Resources

About