Synthesis, structure, and thermochemistry of adduct formation between N-heterocyclic carbenes and isocyanates or mesitylnitrile oxide

Manuel Temprado, Subhojit Majumdar, Xiaochen Cai, Burjor Captain, Carl Hoff

Research output: Contribution to journalArticle

8 Citations (Scopus)

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 languageEnglish
Pages (from-to)2059-2068
Number of pages10
JournalStructural Chemistry
Volume24
Issue number6
DOIs
StatePublished - Dec 1 2013

Fingerprint

Thermochemistry
Isocyanates
isocyanates
thermochemistry
carbenes
Oxides
adducts
Imidoesters
Nitriles
oxides
X ray crystallography
nitriles
Toluene
Calorimetry
synthesis
Discrete Fourier transforms
crystallography
toluene
Enthalpy
heat measurement

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 journalArticle

@article{a1d4078119b1477cb9ec8798fb16d75a,
title = "Synthesis, structure, and thermochemistry of adduct formation between N-heterocyclic carbenes and isocyanates or mesitylnitrile oxide",
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.",
keywords = "Betaines, Carbenes, NHC, Thermochemistry, Zwitterions",
author = "Manuel Temprado and Subhojit Majumdar and Xiaochen Cai and Burjor Captain and Carl Hoff",
year = "2013",
month = "12",
day = "1",
doi = "10.1007/s11224-013-0305-2",
language = "English",
volume = "24",
pages = "2059--2068",
journal = "Structural Chemistry",
issn = "1040-0400",
publisher = "Springer New York",
number = "6",

}

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

VL - 24

SP - 2059

EP - 2068

JO - Structural Chemistry

JF - Structural Chemistry

SN - 1040-0400

IS - 6

ER -