No Contribution of an Inductive Effect to Secondary Deuterium Isotope Effects on Acidity

Perrin, Charles L.; Flach, Agnes

doi:10.1002/anie.201102125

Cited by 23 publications

(24 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…An IE exists if the isotope substitution has a marked effect on the rate constant of the reaction. Such measurements have been used for many decades and have provided methods to investigate compounds' acidities 46 and basicities. 47 In NMR spectroscopy, the IE terminology refers to differences in chemical shift for nuclei that are directly attached to the isotope or that are neighbors to the site of isotope substitution.…”

Section: H-/d-exchange In Nmr Solventmentioning

confidence: 99%

Structure assignment and H/D-exchange behavior of several glycosylated polyphenols

Franz¹,

Serebnitskaya²,

Gudial³

et al. 2014

Arkivoc

View full text Add to dashboard Cite

The NMR-structures of six polyphenols, resveratrol (1), (-)-epicatechin (2), pelargonidin chloride (3), cyanidin chloride (4), cyanin chloride (5), and keracyanin chloride (6), were fully assigned. For the glycosylated polyphenols 5 and 6, the three-dimensional solution structure and long-range 1 H-13 C-coupling constants across the glycosidic bond were measured. Satisfactory fit to standard Karplus-equations was achieved for glycosides directly attached to the aromatic core in cyanin chloride. Molecular dynamics simulation data in vacuum at the AM1-level of theory were shown to approximate the NMR-solution data reasonably well. Selective HCl-catalyzed H/D-exchange was observed for aromatic protons H6 and H8 in flavonoid structures containing a 5,7-metadisubstituted chromelynium core with free OH-groups. The exchange took place readily in compounds 3, 4, and 6, whereas 1, 2, and 5 did not exchange.

show abstract

Section: H-/d-exchange In Nmr Solventmentioning

confidence: 99%

Structure assignment and H/D-exchange behavior of several glycosylated polyphenols

Franz¹,

Serebnitskaya²,

Gudial³

et al. 2014

Arkivoc

View full text Add to dashboard Cite

show abstract

“…Finally, we return to the experimental finding that SDIEs on acidity appear in the enthalpy, with no entropic contribution, 3 which is what prompted Halevi's recent paper.…”

mentioning

confidence: 85%

Comment on “The role of electrostatic induction in secondary isotope effects on acidity” by E. A. Halevi, New J. Chem., 2014, 38, 3840

Perrin

2015

New J. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…After postdoctoral research with Andrew Streitwieser, Jr. at the University of California, Berkeley, he started his independent career at the University of California, San Diego, in 1964 and remains there to this day. Perrin’s research interests are in molecular structure and in mechanisms of organic reactions, including malonic anhydrides, kinetic and equilibrium isotope effects, and the symmetry of hydrogen bonds 11 …”

Section: Awarded …︁mentioning

confidence: 99%

American Chemical Society 2015 National Award Winners

2015

Angew Chem Int Ed

View full text Add to dashboard Cite

No Contribution of an Inductive Effect to Secondary Deuterium Isotope Effects on Acidity

Cited by 23 publications

References 29 publications

Structure assignment and H/D-exchange behavior of several glycosylated polyphenols

Structure assignment and H/D-exchange behavior of several glycosylated polyphenols

Comment on “The role of electrostatic induction in secondary isotope effects on acidity” by E. A. Halevi, New J. Chem., 2014, 38, 3840

American Chemical Society 2015 National Award Winners

Contact Info

Product

Resources

About