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Title: Characterization of Carbenes via Hydrogenation Energies, Stability, and Reactivity: What's in a Name?

Authors:
 [1]; ORCiD logo [2];  [1]; ORCiD logo [1]
  1. Department of Chemistry, The University of Alabama, Shelby Hall, Tuscaloosa Alabama 35487-0336 USA
  2. Department of Chemistry, Washington State University, Pullman WA 99164-4630 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1409477
Grant/Contract Number:  
Catalysis Center Program
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Name: Chemistry - A European Journal Journal Volume: 23 Journal Issue: 69; Journal ID: ISSN 0947-6539
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Vasiliu, Monica, Peterson, Kirk A., Arduengo, Anthony J., and Dixon, David A. Characterization of Carbenes via Hydrogenation Energies, Stability, and Reactivity: What's in a Name?. Germany: N. p., 2017. Web. doi:10.1002/chem.201703539.
Vasiliu, Monica, Peterson, Kirk A., Arduengo, Anthony J., & Dixon, David A. Characterization of Carbenes via Hydrogenation Energies, Stability, and Reactivity: What's in a Name?. Germany. doi:10.1002/chem.201703539.
Vasiliu, Monica, Peterson, Kirk A., Arduengo, Anthony J., and Dixon, David A. Thu . "Characterization of Carbenes via Hydrogenation Energies, Stability, and Reactivity: What's in a Name?". Germany. doi:10.1002/chem.201703539.
@article{osti_1409477,
title = {Characterization of Carbenes via Hydrogenation Energies, Stability, and Reactivity: What's in a Name?},
author = {Vasiliu, Monica and Peterson, Kirk A. and Arduengo, Anthony J. and Dixon, David A.},
abstractNote = {},
doi = {10.1002/chem.201703539},
journal = {Chemistry - A European Journal},
number = 69,
volume = 23,
place = {Germany},
year = {2017},
month = {11}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/chem.201703539

Citation Metrics:
Cited by: 1 work
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Works referenced in this record:

Gaussian-3 theory using reduced Mo/ller-Plesset order
journal, March 1999

  • Curtiss, Larry A.; Redfern, Paul C.; Raghavachari, Krishnan
  • The Journal of Chemical Physics, Vol. 110, Issue 10
  • DOI: 10.1063/1.478385

Generalized Gradient Approximation Made Simple
journal, October 1996

  • Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias
  • Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868
  • DOI: 10.1103/PhysRevLett.77.3865

N-Heterocyclic Carbene-Phosphinidyne Transition Metal Complexes
journal, October 2014

  • Doddi, Adinarayana; Bockfeld, Dirk; Bannenberg, Thomas
  • Angewandte Chemie International Edition, Vol. 53, Issue 49
  • DOI: 10.1002/anie.201408354

Reliable Determination of Amidicity in Acyclic Amides and Lactams
journal, June 2012

  • Glover, Stephen A.; Rosser, Adam A.
  • The Journal of Organic Chemistry, Vol. 77, Issue 13
  • DOI: 10.1021/jo300347k

Electron Distribution in a Stable Carbene
journal, July 1994

  • Arduengo, Anthony J.; Dias, H. V. Rasika; Dixon, David A.
  • Journal of the American Chemical Society, Vol. 116, Issue 15
  • DOI: 10.1021/ja00094a040

A stable crystalline carbene
journal, January 1991

  • Arduengo, Anthony J.; Harlow, Richard L.; Kline, Michael
  • Journal of the American Chemical Society, Vol. 113, Issue 1
  • DOI: 10.1021/ja00001a054

1,3,4,5-Tetramethyl-2-methyleneimidazoline—an ylidic olefin
journal, January 1993

  • Kuhn, Norbert; Bohnen, Hans; Kreutzberg, Jörg
  • J. Chem. Soc., Chem. Commun., Issue 14
  • DOI: 10.1039/C39930001136

Molpro: a general-purpose quantum chemistry program package: Molpro
journal, July 2011

  • Werner, Hans-Joachim; Knowles, Peter J.; Knizia, Gerald
  • Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 2
  • DOI: 10.1002/wcms.82

Accurate Heats of Formation of the “Arduengo-Type” Carbene and Various Adducts Including H 2 from ab Initio Molecular Orbital Theory
journal, February 2006

  • Dixon, David A.; Arduengo, Anthony J.
  • The Journal of Physical Chemistry A, Vol. 110, Issue 5
  • DOI: 10.1021/jp055527i

Electronic Structure of Stable Carbenes, Silylenes, and Germylenes
journal, January 1996

  • Boehme, Christian; Frenking, Gernot
  • Journal of the American Chemical Society, Vol. 118, Issue 8
  • DOI: 10.1021/ja9527075

PhenoFluor: Practical Synthesis, New Formulation, and Deoxyfluorination of Heteroaromatics
journal, July 2014

  • Fujimoto, Teppei; Becker, Fabian; Ritter, Tobias
  • Organic Process Research & Development, Vol. 18, Issue 8
  • DOI: 10.1021/op500121w

Ein stabiles Tetraazafulvalen
journal, May 1996


Improved synthesis of N-heterocyclic olefins and evaluation of their donor strengths
journal, March 2016


Heats of Formation of Simple Perfluorinated Carbon Compounds
journal, June 1999

  • Dixon, David A.; Feller, David; Sandrone, Giovanni
  • The Journal of Physical Chemistry A, Vol. 103, Issue 24
  • DOI: 10.1021/jp990425b

Analogous .alpha.,.alpha.'-bis-carbenoid, triply bonded species: synthesis of a stable .lambda.3-phosphino carbene-.lambda.5-phosphaacetylene
journal, September 1988

  • Igau, Alain.; Grutzmacher, Hansjorg.; Baceiredo, Antoine.
  • Journal of the American Chemical Society, Vol. 110, Issue 19
  • DOI: 10.1021/ja00227a028

Chemical Shielding Tensor of a Carbene
journal, July 1994

  • Arduengo, Anthony J.; Dixon, David A.; Kumashiro, Kristin K.
  • Journal of the American Chemical Society, Vol. 116, Issue 14
  • DOI: 10.1021/ja00093a041

Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen
journal, January 1989

  • Dunning, Thom H.
  • The Journal of Chemical Physics, Vol. 90, Issue 2
  • DOI: 10.1063/1.456153

Electronegativity: The density functional viewpoint
journal, April 1978

  • Parr, Robert G.; Donnelly, Robert A.; Levy, Mel
  • The Journal of Chemical Physics, Vol. 68, Issue 8
  • DOI: 10.1063/1.436185

Stable Carbenes
journal, January 2000

  • Bourissou, Didier; Guerret, Olivier; Gabbaï, François P.
  • Chemical Reviews, Vol. 100, Issue 1
  • DOI: 10.1021/cr940472u

The resonance energy of amides, the structure of aziridinone, and its relationship to other strained lactams
journal, February 1991

  • Greenberg, Arthur; Chiu, Yeu-Yi; Johnson, Jeri L.
  • Structural Chemistry, Vol. 2, Issue 2
  • DOI: 10.1007/BF00676622

Amidicity Change as a Significant Driving Force and Thermodynamic Selection Rule of Transamidation Reactions. A Synergy between Experiment and Theory
journal, July 2008

  • Mucsi, Zoltán; Chass, Gregory A.; Csizmadia, Imre G.
  • The Journal of Physical Chemistry B, Vol. 112, Issue 26
  • DOI: 10.1021/jp8023292

NBO 6.0 : Natural bond orbital analysis program
journal, March 2013

  • Glendening, Eric D.; Landis, Clark R.; Weinhold, Frank
  • Journal of Computational Chemistry, Vol. 34, Issue 16
  • DOI: 10.1002/jcc.23266

Calculation of negative electron affinity and aqueous anion hardness using Kohn–Sham HOMO and LUMO energies
journal, January 2007

  • De Proft, Frank; Sablon, Nick; Tozer, David J.
  • Faraday Discuss., Vol. 135
  • DOI: 10.1039/B605302P

Looking for Stable Carbenes:  The Difficulty in Starting Anew
journal, November 1999

  • Arduengo, Anthony J.
  • Accounts of Chemical Research, Vol. 32, Issue 11
  • DOI: 10.1021/ar980126p

Further benchmarks of a composite, convergent, statistically calibrated coupled-cluster-based approach for thermochemical and spectroscopic studies
journal, April 2012


A second order multiconfiguration SCF procedure with optimum convergence
journal, June 1985

  • Werner, Hans‐Joachim; Knowles, Peter J.
  • The Journal of Chemical Physics, Vol. 82, Issue 11
  • DOI: 10.1063/1.448627

Intercepting low oxidation state main group hydrides with a nucleophilic N-heterocyclic olefin
journal, January 2011

  • Ibrahim Al-Rafia, S. M.; Malcolm, Adam C.; Liew, Sean K.
  • Chemical Communications, Vol. 47, Issue 24
  • DOI: 10.1039/c1cc11737h

A Quantitative Scale for the Extent of Conjugation of the Amide Bond. Amidity Percentage as a Chemical Driving Force
journal, December 2007

  • Mucsi, Zoltán; Tsai, Alex; Szori, Milan
  • The Journal of Physical Chemistry A, Vol. 111, Issue 50
  • DOI: 10.1021/jp0759325

The complete active space SCF (CASSCF) method in a Newton–Raphson formulation with application to the HNO molecule
journal, February 1981

  • Siegbahn, Per E. M.; Almlöf, Jan; Heiberg, Anders
  • The Journal of Chemical Physics, Vol. 74, Issue 4
  • DOI: 10.1063/1.441359

Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
journal, September 1988

  • Reed, Alan E.; Curtiss, Larry A.; Weinhold, Frank
  • Chemical Reviews, Vol. 88, Issue 6
  • DOI: 10.1021/cr00088a005

Optimization of Gaussian-type basis sets for local spin density functional calculations. Part I. Boron through neon, optimization technique and validation
journal, February 1992

  • Godbout, Nathalie; Salahub, Dennis R.; Andzelm, Jan
  • Canadian Journal of Chemistry, Vol. 70, Issue 2
  • DOI: 10.1139/v92-079

An efficient second-order MC SCF method for long configuration expansions
journal, April 1985


Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993

  • Becke, Axel D.
  • The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
  • DOI: 10.1063/1.464913

Bond Energies in Models of the Schrock Metathesis Catalyst
journal, May 2011

  • Vasiliu, Monica; Li, Shenggang; Arduengo, Anthony J.
  • The Journal of Physical Chemistry C, Vol. 115, Issue 24
  • DOI: 10.1021/jp202668p

A complete active space SCF method (CASSCF) using a density matrix formulated super-CI approach
journal, May 1980


Carbene-Based Lewis Pairs for Hydrogen Activation
journal, January 2011

  • Runyon, Jason W.; Steinhof, Oliver; Dias, H. V. Rasika
  • Australian Journal of Chemistry, Vol. 64, Issue 8
  • DOI: 10.1071/CH11246

Computation of the Hardness and the Problem of Negative Electron Affinities in Density Functional Theory
journal, October 2005

  • Tozer, David J.; De Proft, Frank
  • The Journal of Physical Chemistry A, Vol. 109, Issue 39
  • DOI: 10.1021/jp053504y

Generalized Gradient Approximation Made Simple [Phys. Rev. Lett. 77, 3865 (1996)]
journal, February 1997


Conceptual Density Functional Theory
journal, May 2003

  • Geerlings, P.; De Proft, F.; Langenaeker, W.
  • Chemical Reviews, Vol. 103, Issue 5
  • DOI: 10.1021/cr990029p

Photoelectron Spectroscopy of a Carbene/Silylene/Germylene Series
journal, July 1994

  • Arduengo, Anthony J.; Bock, Hans; Chen, Han
  • Journal of the American Chemical Society, Vol. 116, Issue 15
  • DOI: 10.1021/ja00094a020

Stabilities of Carbenes: Independent Measures for Singlets and Triplets
journal, March 2011

  • Gronert, Scott; Keeffe, James R.; More O’Ferrall, Rory A.
  • Journal of the American Chemical Society, Vol. 133, Issue 10
  • DOI: 10.1021/ja1071493

Chemical accuracy in ab initio thermochemistry and spectroscopy: current strategies and future challenges
journal, January 2012

  • Peterson, Kirk A.; Feller, David; Dixon, David A.
  • Theoretical Chemistry Accounts, Vol. 131, Issue 1
  • DOI: 10.1007/s00214-011-1079-5

Absolute hardness: companion parameter to absolute electronegativity
journal, December 1983

  • Parr, Robert G.; Pearson, Ralph G.
  • Journal of the American Chemical Society, Vol. 105, Issue 26
  • DOI: 10.1021/ja00364a005

Density-Functional Theory of the Electronic Structure of Molecules
journal, October 1995


An Air Stable Carbene and Mixed Carbene “Dimers”
journal, December 1997

  • Arduengo, Anthony J.; Davidson, Frederic; Dias, H. V. R.
  • Journal of the American Chemical Society, Vol. 119, Issue 52
  • DOI: 10.1021/ja973241o

Electronic stabilization of nucleophilic carbenes
journal, July 1992

  • Arduengo, Anthony J.; Dias, H. V. Rasika; Harlow, Richard L.
  • Journal of the American Chemical Society, Vol. 114, Issue 14
  • DOI: 10.1021/ja00040a007

Absolute electronegativity and hardness correlated with molecular orbital theory
journal, November 1986


A Brief Survey of Our Contribution to Stable Carbene Chemistry
journal, October 2011

  • Martin, David; Melaimi, Mohand; Soleilhavoup, Michele
  • Organometallics, Vol. 30, Issue 20
  • DOI: 10.1021/om200650x

A Stable Tetraazafulvalene
journal, May 1996

  • Taton, T. Andrew; Chen, Peter
  • Angewandte Chemie International Edition in English, Vol. 35, Issue 9
  • DOI: 10.1002/anie.199610111

N-Heterocyclic Carbene-Phosphinidyne Transition Metal Complexes
journal, October 2014

  • Doddi, Adinarayana; Bockfeld, Dirk; Bannenberg, Thomas
  • Angewandte Chemie, Vol. 126, Issue 49
  • DOI: 10.1002/ange.201408354

Electronic structure of phosphine. Effect of basic set and correlation on the inversion barrier
journal, March 1982

  • Marynick, Dennis S.; Dixon, David A.
  • The Journal of Physical Chemistry, Vol. 86, Issue 6
  • DOI: 10.1021/j100395a015

A survey of factors contributing to accurate theoretical predictions of atomization energies and molecular structures
journal, November 2008

  • Feller, David; Peterson, Kirk A.; Dixon, David A.
  • The Journal of Chemical Physics, Vol. 129, Issue 20
  • DOI: 10.1063/1.3008061

Trifluoroethylidynesulfur Trifluoride, F3CCSF3
journal, February 1984

  • Pötter, Brigitte; Seppelt, Konrad
  • Angewandte Chemie International Edition in English, Vol. 23, Issue 2
  • DOI: 10.1002/anie.198401501