Hydrogen Bonding of N‐Heterocyclic Carbenes in Solution: Mechanisms of Solvent Reorganization

2018 ◽  
Vol 24 (45) ◽  
pp. 11594-11604 ◽  
Author(s):  
Sascha Gehrke ◽  
Oldamur Hollóczki
Keyword(s):  
Hydrogen Bonding ◽  
Heterocyclic Carbenes

N-Heterocyclic Carbenes and Parent Cations: Acidity, Nucleophilicity, Stability, and Hydrogen Bonding-Electrochemical Study and Ab Initio Calculations

2016 ◽  
Vol 3 (7) ◽  
pp. 1133-1141 ◽  
Author(s):  
Marta Feroci ◽  
Isabella Chiarotto ◽  
Francesca D'Anna ◽  
Fabrizio Gala ◽  
Renato Noto ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Ab Initio Calculations ◽  
Ab Initio ◽  
Heterocyclic Carbenes ◽  
Electrochemical Study

Anion-Exchange-Triggered 1,3-Shift of an NH Proton to Iridium in Protic N-Heterocyclic Carbenes: Hydrogen-Bonding and Ion-Pairing Effects

2009 ◽  
Vol 49 (5) ◽  
pp. 912-917 ◽  
Author(s):  
Guoyong Song ◽  
Yan Su ◽  
Roy A. Periana ◽  
Robert H. Crabtree ◽  
Keli Han ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Anion Exchange ◽  
Ion Pairing ◽  
Heterocyclic Carbenes

scholarly journals Preferential N–H⋯:C hydrogen bonding involving ditopic NH-containing systems and N-heterocyclic carbenes

RSC Advances ◽  
2020 ◽  
Vol 10 (69) ◽  
pp. 42164-42171
Author(s):  
Zacharias J. Kinney ◽  
Arnold L. Rheingold ◽  
John D. Protasiewicz
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Heterocyclic Carbenes ◽  
Secondary Amines ◽  
Solution State

Non-traditional hydrogen bonds between a singlet carbene and a series of ditopic secondary amines is detailed. Both the solid- and solution-state metrics reveal the strength of these associations are dependent on the pKa of the NH-containing molecule.

Unveiling the peculiar hydrogen bonding behavior of solvated N-heterocyclic carbenes

2016 ◽  
Vol 18 (1) ◽  
pp. 126-140 ◽  
Author(s):  
Oldamur Hollóczki
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Force Field ◽  
Practical Importance ◽  
Md Simulations ◽  
Heterocyclic Carbenes ◽  
Mechanical Force

After fitting a molecular mechanical force field for imidazol-2-ylidenes, MD simulations revealed carbene–carbene and three-center hydrogen bonds of carbenes. The practical importance of these structures is also highlighted.

Anion-Exchange-Triggered 1,3-Shift of an NH Proton to Iridium in Protic N-Heterocyclic Carbenes: Hydrogen-Bonding and Ion-Pairing Effects

2010 ◽  
Vol 122 (5) ◽  
pp. 924-929 ◽  
Author(s):  
Guoyong Song ◽  
Yan Su ◽  
Roy A. Periana ◽  
Robert H. Crabtree ◽  
Keli Han ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Anion Exchange ◽  
Ion Pairing ◽  
Heterocyclic Carbenes

Recent Progress in Equilibrium Acidity Studies of Organocatalysts

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1940-1949 ◽  
Author(s):  
Zhen Li ◽  
Xin Li ◽  
Jin-Pei Cheng
Keyword(s):  
Hydrogen Bonding ◽  
High Accuracy ◽  
Heterocyclic Carbenes ◽  
Cinchona Alkaloids ◽  
Acid Catalysts ◽  
Hydrogen Bond Donor ◽  
Indicator Method ◽  
Linear Free Energy ◽  
Energy Relationships ◽  
Double Hydrogen

This account summarizes our recent work on the pK a scales of some frequently used organocatalysts, especially those of hydrogen-bond-donor catalysts and stronger Brønsted acid catalysts. Most of these pK a values were obtained by the Bordwell overlapping indicator method, which is known to provide high accuracy. Linear free-energy relationships associated with pK a values are discussed in relation to understanding of reaction mechanisms.1 Introduction2 Single Hydrogen-Bonding Donors2.1 Proline-Type Organocatalysts2.2 Cinchona Alkaloids Bearing a Hydrogen-Bonding Donor in the 6′-Position3 Double-Hydrogen-Bonding Donors3.1 Thioureas3.2 Squaramides3.3 BINOLs4 Stronger Brønsted Acids5 N-Heterocyclic Carbenes6 Summary and Outlook

Hydrogen-Bonding Pincer Complexes with Two Protic N-Heterocyclic Carbenes from Direct Metalation of a 1,8-Bis(imidazol-1-yl)carbazole by Platinum, Palladium, and Nickel

2015 ◽  
Vol 21 (31) ◽  
pp. 10988-10992 ◽  
Author(s):  
David C. Marelius ◽  
Evan H. Darrow ◽  
Curtis E. Moore ◽  
James A. Golen ◽  
Arnold L. Rheingold ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Heterocyclic Carbenes ◽  
Pincer Complexes

Hydrogen bonding in liquid methanol at ambient conditions and at high pressure

2000 ◽  
Vol 98 (3) ◽  
pp. 125-134 ◽  
Author(s):  
T. Weitkamp, J. Neuefeind, H. E. Fisch
Keyword(s):  
High Pressure ◽  
Hydrogen Bonding ◽  
Ambient Conditions
Sign in / Sign up

Export Citation Format

Share Document