Abstract
Reaction of N-heterocyclic carbenes (NHCs) with isocyanates yields stable zwitterionic imidates/amidates in toluene solution. These compounds were fully characterized and the crystal structures of several species were determined by X-ray crystallography. The thermochemistry of binding of these and related species was studied by solution calorimetry. Comparison is made of the enthalpies of binding of NHC to isocyanates (RNCO) and isomeric nitrile oxides (RCNO) as well as CO2. DFT calculations were performed to additionally assess the nature of bonding in these compounds.
| Original language | English |
|---|---|
| Pages (from-to) | 2059-2068 |
| Number of pages | 10 |
| Journal | Structural Chemistry |
| Volume | 24 |
| Issue number | 6 |
| DOIs | |
| State | Published - Dec 1 2013 |
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Keywords
- Betaines
- Carbenes
- NHC
- Thermochemistry
- Zwitterions
ASJC Scopus subject areas
- Condensed Matter Physics
- Physical and Theoretical Chemistry
Cite this
Synthesis, structure, and thermochemistry of adduct formation between N-heterocyclic carbenes and isocyanates or mesitylnitrile oxide. / Temprado, Manuel; Majumdar, Subhojit; Cai, Xiaochen; Captain, Burjor; Hoff, Carl.
In: Structural Chemistry, Vol. 24, No. 6, 01.12.2013, p. 2059-2068.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis, structure, and thermochemistry of adduct formation between N-heterocyclic carbenes and isocyanates or mesitylnitrile oxide
AU - Temprado, Manuel
AU - Majumdar, Subhojit
AU - Cai, Xiaochen
AU - Captain, Burjor
AU - Hoff, Carl
PY - 2013/12/1
Y1 - 2013/12/1
N2 - Reaction of N-heterocyclic carbenes (NHCs) with isocyanates yields stable zwitterionic imidates/amidates in toluene solution. These compounds were fully characterized and the crystal structures of several species were determined by X-ray crystallography. The thermochemistry of binding of these and related species was studied by solution calorimetry. Comparison is made of the enthalpies of binding of NHC to isocyanates (RNCO) and isomeric nitrile oxides (RCNO) as well as CO2. DFT calculations were performed to additionally assess the nature of bonding in these compounds.
AB - Reaction of N-heterocyclic carbenes (NHCs) with isocyanates yields stable zwitterionic imidates/amidates in toluene solution. These compounds were fully characterized and the crystal structures of several species were determined by X-ray crystallography. The thermochemistry of binding of these and related species was studied by solution calorimetry. Comparison is made of the enthalpies of binding of NHC to isocyanates (RNCO) and isomeric nitrile oxides (RCNO) as well as CO2. DFT calculations were performed to additionally assess the nature of bonding in these compounds.
KW - Betaines
KW - Carbenes
KW - NHC
KW - Thermochemistry
KW - Zwitterions
UR - http://www.scopus.com/inward/record.url?scp=84889087211&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84889087211&partnerID=8YFLogxK
U2 - 10.1007/s11224-013-0305-2
DO - 10.1007/s11224-013-0305-2
M3 - Article
AN - SCOPUS:84889087211
VL - 24
SP - 2059
EP - 2068
JO - Structural Chemistry
JF - Structural Chemistry
SN - 1040-0400
IS - 6
ER -