Bond Dissociation Energies of Carbene–Carbene and Carbene–Main Group Adducts

Vasiliu, Monica; Edwards, Kyle C.; Tapu, Daniela; Castillo, Clarisa E.; Stein, Trent H.; Craciun, Raluca; Arduengo, Anthony J.; Dixon, David A.

doi:10.1021/acs.jpca.2c00921

Bond Dissociation Energies of Carbene–Carbene and Carbene–Main Group Adducts

Journal Article · 20 April 2022 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.2c00921· OSTI ID:1981889

Vasiliu, Monica ^[1]; Edwards, Kyle C. ^[1]; ^[2]; Castillo, Clarisa E. ^[1]; Stein, Trent H. ^[1]; Craciun, Raluca ^[1]; Arduengo, Anthony J. ^[3]; ^[1]

Department of Chemistry and Biochemistry, The University of Alabama, Tuscaloosa, Alabama 35487-0336, United States
Department of Chemistry and Biochemistry, Kennesaw State University, Kennesaw, Georgia 30144, United States
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, United States

Not provided.

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Center for Scalable Predictive Methods for Excitations and Correlated Phenomena (SPEC)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1981889

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 17 Vol. 126; ISSN 1089-5639

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (52)

Characterization of Carbenes via Hydrogenation Energies, Stability, and Reactivity: What's in a Name? Vasiliu, Monica; Peterson, Kirk A.; Arduengo, Anthony J. Chemistry – A European Journal, Vol. 23, Issue 69 https://doi.org/10.1002/chem.201703539	journal	November 2017
Absolute hardness: companion parameter to absolute electronegativity Parr, Robert G.; Pearson, Ralph G. Journal of the American Chemical Society, Vol. 105, Issue 26 https://doi.org/10.1021/ja00364a005	journal	December 1983
Generation and Coordinating Properties of a Carbene Bearing a Phosphorus Ylide: An Intensely Electron-Donating Ligand Nakafuji, Shin-ya; Kobayashi, Junji; Kawashima, Takayuki Angewandte Chemie International Edition, Vol. 47, Issue 6 https://doi.org/10.1002/anie.200704746	journal	January 2008
Bond Dissociation Energies in Second-Row Compounds Grant, Daniel J.; Matus, Myrna H.; Switzer, Jackson R. The Journal of Physical Chemistry A, Vol. 112, Issue 14 https://doi.org/10.1021/jp710373e	journal	April 2008
Trifluoroethylidynesulfur trifluoride, CF3C.tplbond.SF3, and its dimer Poetter, Brigitte; Seppelt, Konrad; Simon, Arndt Journal of the American Chemical Society, Vol. 107, Issue 4 https://doi.org/10.1021/ja00290a038	journal	February 1985
Synthesis of an Extremely Bent Acyclic Allene (A “Carbodicarbene”): A Strong Donor Ligand Dyker, C. Adam; Lavallo, Vincent; Donnadieu, Bruno Angewandte Chemie International Edition, Vol. 47, Issue 17 https://doi.org/10.1002/anie.200705620	journal	April 2008
Correlating Electronic Properties of N ‐Heterocyclic Carbenes with Structure, and the Implications of Using Different Probes Barnett, Christopher; Harper, Jason B.; Cole, Marcus L. ChemistrySelect, Vol. 7, Issue 2 https://doi.org/10.1002/slct.202104348	journal	January 2022
Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory Lavallo, V. Science, Vol. 312, Issue 5774 https://doi.org/10.1126/science.1126675	journal	May 2006
The Measure of All Rings-N-Heterocyclic Carbenes Dröge, Thomas; Glorius, Frank Angewandte Chemie International Edition, Vol. 49, Issue 39 https://doi.org/10.1002/anie.201001865	journal	August 2010
Relation between singlet-triplet gaps and bond energies Carter, Emily A.; Goddard, William A. The Journal of Physical Chemistry, Vol. 90, Issue 6 https://doi.org/10.1021/j100278a006	journal	March 1986
A tetranuclear molecular rectangle from four gold(I) atoms linked by dicarbene and diphosphine ligands Radloff, Christian; Weigand, Jan J.; Hahn, F. Ekkehardt Dalton Transactions, Issue 43 https://doi.org/10.1039/b916651c	journal	January 2009
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Derivate des Imidazols, XIX. Koordination oder Reduktion? Zur Reaktion von 1,3‐Diisopropyl‐4,5‐dimethylimidazol‐2‐yliden mit Schwefelhalogeniden und Schwefeloxidhalogeniden Kuhn, Norbert; Bohnen, Hans; Fahl, Joanna Chemische Berichte, Vol. 129, Issue 12 https://doi.org/10.1002/cber.19961291228	journal	December 1996
A new inversion process at Group VA (Group 15) elements. Edge inversion through a planar T-shaped structure Dixon, David A.; Arduengo, Anthony J.; Fukunaga, Tadamichi. Journal of the American Chemical Society, Vol. 108, Issue 9 https://doi.org/10.1021/ja00269a063	journal	April 1986
Solvent stabilization of the edge inversion transition state in tetrahedral molecules Dixon, David A.; Arduengo, Anthony J. International Journal of Quantum Chemistry, Vol. 34, Issue S22 https://doi.org/10.1002/qua.560340814	journal	March 1988
Understanding the M(NHC) (NHC=N-heterocyclic carbene) bond Jacobsen, Heiko; Correa, Andrea; Poater, Albert Coordination Chemistry Reviews, Vol. 253, Issue 5-6 https://doi.org/10.1016/j.ccr.2008.06.006	journal	March 2009
Analogous .alpha.,.alpha.'-bis-carbenoid, triply bonded species: synthesis of a stable .lambda.3-phosphino carbene-.lambda.5-phosphaacetylene Igau, Alain.; Grutzmacher, Hansjorg.; Baceiredo, Antoine. Journal of the American Chemical Society, Vol. 110, Issue 19 https://doi.org/10.1021/ja00227a028	journal	September 1988
Synthesis and Reactivity of a CAAC-Aminoborylene Adduct: A Hetero-Allene or an Organoboron Isoelectronic with Singlet Carbenes Dahcheh, Fatme; Martin, David; Stephan, Douglas W. Angewandte Chemie, Vol. 126, Issue 48 https://doi.org/10.1002/ange.201408371	journal	September 2014
Reactions of Arylcarbenes with Lewis Acids Raut, Akshay Hemant; Costa, Paolo; Sander, Wolfram Chemistry – A European Journal, Vol. 24, Issue 68 https://doi.org/10.1002/chem.201803695	journal	November 2018
Stability and Structure of Carbene-Derived Neutral Penta- and Hexacoordinate Silicon Complexes Hollóczki, Oldamur; Nyulászi, László Organometallics, Vol. 28, Issue 14 https://doi.org/10.1021/om9002768	journal	June 2009
Lewis Acidity and Basicity: Another Measure of Carbene Reactivity Stein, Trent H.; Vasiliu, Monica; Arduengo, Anthony J. The Journal of Physical Chemistry A, Vol. 124, Issue 29 https://doi.org/10.1021/acs.jpca.0c03877	journal	June 2020
Stable Carbenes Bourissou, Didier; Guerret, Olivier; Gabbaï, François P. Chemical Reviews, Vol. 100, Issue 1 https://doi.org/10.1021/cr940472u	journal	January 2000
A stable crystalline carbene Arduengo, Anthony J.; Harlow, Richard L.; Kline, Michael Journal of the American Chemical Society, Vol. 113, Issue 1 https://doi.org/10.1021/ja00001a054	journal	January 1991
A Brief Survey of Our Contribution to Stable Carbene Chemistry Martin, David; Melaimi, Mohand; Soleilhavoup, Michele Organometallics, Vol. 30, Issue 20 https://doi.org/10.1021/om200650x	journal	October 2011
Optimization of Gaussian-type basis sets for local spin density functional calculations. Part I. Boron through neon, optimization technique and validation Godbout, Nathalie; Salahub, Dennis R.; Andzelm, Jan Canadian Journal of Chemistry, Vol. 70, Issue 2 https://doi.org/10.1139/v92-079	journal	February 1992
Stable Aminooxy- and Aminothiocarbenes Alder, Roger. W.; Butts, Craig P.; Orpen, A. Guy Journal of the American Chemical Society, Vol. 120, Issue 44 https://doi.org/10.1021/ja9819312	journal	November 1998
A Stable P-Heterocyclic Carbene Martin, David; Baceiredo, Antoine; Gornitzka, Heinz Angewandte Chemie International Edition, Vol. 44, Issue 11 https://doi.org/10.1002/anie.200462239	journal	March 2005
Stretching the P–C Bond. Variations on Carbenes and Phosphanes Buzsáki, Dániel; Kelemen, Zsolt; Nyulászi, László The Journal of Physical Chemistry A, Vol. 124, Issue 13 https://doi.org/10.1021/acs.jpca.0c00641	journal	March 2020
A Benzobisimidazolium-Based Fluorescent and Colorimetric Chemosensor for CO₂ Guo, Zhiqian; Song, Na Ri; Moon, Jong Hun Journal of the American Chemical Society, Vol. 134, Issue 43 https://doi.org/10.1021/ja306891c	journal	September 2012
N-Heterocyclic Carbenes in Late Transition Metal Catalysis Díez-González, Silvia; Marion, Nicolas; Nolan, Steven P. Chemical Reviews, Vol. 109, Issue 8 https://doi.org/10.1021/cr900074m	journal	August 2009
Trifluoroethylidynesulfur Trifluoride, F3CCSF3 Pötter, Brigitte; Seppelt, Konrad Angewandte Chemie International Edition in English, Vol. 23, Issue 2 https://doi.org/10.1002/anie.198401501	journal	February 1984
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Synthetic Routes to N-Heterocyclic Carbene Precursors Benhamou, Laure; Chardon, Edith; Lavigne, Guy Chemical Reviews, Vol. 111, Issue 4 https://doi.org/10.1021/cr100328e	journal	January 2011
Heterocyclic Carbenes: Synthesis and Coordination Chemistry Hahn, F. Ekkehardt; Jahnke, Mareike C. Angewandte Chemie International Edition, Vol. 47, Issue 17 https://doi.org/10.1002/anie.200703883	journal	April 2008
Ab Initio Coupled Cluster Determination of the Heats of Formation of C ₂ H ₂ F ₂ , C ₂ F ₂ , and C ₂ F ₄ Feller, David; Peterson, Kirk A.; Dixon, David A. The Journal of Physical Chemistry A, Vol. 115, Issue 8 https://doi.org/10.1021/jp111644h	journal	March 2011
Carbenes: Synthesis, properties, and organometallic chemistry de Frémont, Pierre; Marion, Nicolas; Nolan, Steven P. Coordination Chemistry Reviews, Vol. 253, Issue 7-8 https://doi.org/10.1016/j.ccr.2008.05.018	journal	April 2009
Neutral Penta- and Hexacoordinate N-Heterocyclic Carbene Complexes Derived from SiX₄(X = F, Br) Ghadwal, Rajendra S.; Sen, Sakya S.; Roesky, Herbert W. Organometallics, Vol. 28, Issue 21 https://doi.org/10.1021/om9007696	journal	October 2009
Photoelectron spectroscopy of the aluminum hydride anions: AlH ₂ ⁻ , AlH ₃ ⁻ , Al ₂ H ₆ ⁻ , Al ₃ H ₉ ⁻ , and Al ₄ H ₁₂ ⁻ Zhang, Xinxing; Wang, Haopeng; Collins, Evan The Journal of Chemical Physics, Vol. 138, Issue 12 https://doi.org/10.1063/1.4796200	journal	March 2013
Gaussian-3 theory using reduced Mo/ller-Plesset order Curtiss, Larry A.; Redfern, Paul C.; Raghavachari, Krishnan The Journal of Chemical Physics, Vol. 110, Issue 10 https://doi.org/10.1063/1.478385	journal	March 1999
Oxidation of poly(enetetramine)s: a new strategy for the synthesis of conjugated polyelectrolytes Tennyson, Andrew G.; Kamplain, Justin W.; Bielawski, Christopher W. Chemical Communications, Issue 16 https://doi.org/10.1039/b902030f	journal	January 2009
Revisit to imidazolium receptors for the recognition of anions: highlighted research during 2006–2009 Xu, Zhaochao; Kim, Sook Kyung; Yoon, Juyoung Chemical Society Reviews, Vol. 39, Issue 5 https://doi.org/10.1039/b918937h	journal	January 2010
NBO 7.0 : New vistas in localized and delocalized chemical bonding theory Glendening, Eric D.; Landis, Clark R.; Weinhold, Frank Journal of Computational Chemistry https://doi.org/10.1002/jcc.25873	journal	June 2019
Tricoordinate hypervalent sulfur compounds Arduengo, A. J.; Burgess, Edward M. Journal of the American Chemical Society, Vol. 99, Issue 7 https://doi.org/10.1021/ja00449a078	journal	March 1977
Organocatalysis by N-Heterocyclic Carbenes Enders, Dieter; Niemeier, Oliver; Henseler, Alexander Chemical Reviews, Vol. 107, Issue 12, p. 5606-5655 https://doi.org/10.1021/cr068372z	journal	December 2007
The carbon-carbon double bond of tetrafluoroethylene Carter, Emily A.; Goddard, William A. Journal of the American Chemical Society, Vol. 110, Issue 12 https://doi.org/10.1021/ja00220a079	journal	June 1988
Stereoelectronic parameters associated with N-heterocyclic carbene (NHC) ligands: A quest for understanding Díez-González, Silvia; Nolan, Steven P. Coordination Chemistry Reviews, Vol. 251, Issue 5-6 https://doi.org/10.1016/j.ccr.2006.10.004	journal	March 2007
Correction to “Ab Initio Coupled Cluster Determination of the Heats of Formation of C₂H₂F₂, C₂F₂, and C₂F₄” Feller, David; Peterson, Kirk A.; Dixon, David A. The Journal of Physical Chemistry A, Vol. 115, Issue 14 https://doi.org/10.1021/jp202158j	journal	March 2011
Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Reed, Alan E.; Curtiss, Larry A.; Weinhold, Frank Chemical Reviews, Vol. 88, Issue 6 https://doi.org/10.1021/cr00088a005	journal	September 1988
A Stable Thiazol-2-ylidene and Its Dimer Arduengo, Anthony J.; Goerlich, Jens R.; Marshall, William J. Liebigs Annalen, Vol. 1997, Issue 2 https://doi.org/10.1002/jlac.199719970213	journal	February 1997
Beyond catalysis: N-heterocyclic carbene complexes as components for medicinal, luminescent, and functional materials applications Mercs, Laszlo; Albrecht, Martin Chemical Society Reviews, Vol. 39, Issue 6 https://doi.org/10.1039/b902238b	journal	January 2010
Computational Studies of the Properties of Azole· x BH ₃ Adducts for Chemical Hydrogen Storage Systems Vasiliu, Monica; Arduengo, Anthony J.; Dixon, David A. The Journal of Physical Chemistry C, Vol. 116, Issue 42 https://doi.org/10.1021/jp306600c	journal	October 2012
Introduction to Active Thermochemical Tables: Several “Key” Enthalpies of Formation Revisited ^† Ruscic, Branko; Pinzon, Reinhardt E.; Morton, Melita L. The Journal of Physical Chemistry A, Vol. 108, Issue 45 https://doi.org/10.1021/jp047912y	journal	November 2004

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