Computational methods for contemporary carbene chemistry

Wiley Interdisciplinary Reviews: Computational Molecular Science

Volumn 3, Issue 3, 2013, Pages 242-272

  Gerbig, Dennis ^a   Ley, David ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO CALCULATIONS; CARBENE CHEMISTRY; COMPUTATIONAL APPROACH; COMPUTATIONAL PROBLEM; COMPUTING TECHNOLOGY; EXPERIMENTAL STUDIES; THEORETICAL CHEMISTRY; TRIPLET CARBENES;

CALCULATIONS; CHEMICAL BONDS; COMPUTATIONAL METHODS; ORGANIC COMPOUNDS;

COMPUTATIONAL CHEMISTRY;

EID: 84876483344     PISSN: 17590876     EISSN: 17590884     Source Type: Journal    
DOI: 10.1002/wcms.1124     Document Type: Review

References (198)

1. 5-phosphaacetylene. J Am Chem Soc 1988, 110:6463-6466.
2. Wanzlick H-W, Schikora E. Ein neuer Zugang zur Carben-Chemie. Angew Chem 1960, 72:494.
3. Wanzlick H-W, Schikora E. Ein nucleophiles Carben. Chem Ber 1961, 94:2389-2393.
4. Wanzlick H-W. Nucleophile Carben-Chemie. Angew Chem 1962, 74:129-134.
5. Arduengo AJ, Harlow RL, Kline M. A stable crystalline carbene. J Am Chem Soc 1991, 113:361-363.
6. Arduengo AJ. Looking for stable carbenes: the difficulty in starting anew. Acc Chem Res 1999, 32:913-921.
7. Kirmse W. The beginnings of N-heterocyclic carbenes. Angew Chem Int Edit 2010, 49:8798-8801.
8. Enders D, Breuer K, Raabe G, Runsink J, Teles JH, Melder J-P, Ebel K, Brode S. Darstellung, Struktur und Reaktivität von 1, 3, 4-Triphenyl-4, 5-dihydro-1H-1, 2, 4-triazol-5-yliden, einem neuen stabilen Carben. Angew Chem 1995, 107:1119-1122.
9. Bourissou D, Guerret O, Gabbai FP, Bertrand G. Stable carbenes. Chem Rev 2000, 100:39-92.
10. Monguchi K, Itoh T, Hirai K, Tomioka H. Triplet diphenylcarbenes protected by o-aryl groups. J Am Chem Soc 2004, 126:11900-11913.
11. Itoh T, Nakata Y, Hirai K, Tomioka H. Triplet diphenylcarbenes protected by trifluoromethyl and bromine groups. A triplet carbene surviving a day in solution at room temperature. J Am Chem Soc 2006, 128:957-967.
12. Kawano M, Hirai K, Tomioka H, Ohashi Y. Structure determination of triplet diphenylcarbenes by in situ x-ray crystallographic analysis. J Am Chem Soc 2007, 129:2383-2391.
13. Hirai K, Itoh T, Tomioka H. Persistent triplet carbenes. Chem Rev 2009, 109:3275-3332.
14. Hirai K, Bessho K, Kitagawa T, Tomioka H. Triplet diphenylcarbene protected by iodine and bromine groups. J Phys Org Chem 2010, 23:347-356.
15. 3: direct generation and spectroscopic identification of ethylidene's cousin. J Am Chem Soc 2005, 127:12156-12157.
16. Nemirowski A, Schreiner PR. Electronic stabilization of ground state triplet carbenes. J Org Chem 2007, 72:9533-9540.
17. 6 potential energy surface revealed. J Org Chem 1996, 61:7030-7039.
18. 6 energy surface. J Org Chem 1996, 61:7022-7029.
19. Matzinger S, Bally T. Spectroscopic characterization of matrix-isolated phenylcarbene and cycloheptatetraene. J Phys Chem A 2000, 104:3544-3552.
20. von E., Doering W, Hoffmann AK. The addition of dichlorocarbene to olefins. J Am Chem Soc 1954, 76:6162-6165.
21. Skell PS, Garner AY. Reactions of bivalent carbon compounds. reactivities in olefin-dibromocarbene reactions. J Am Chem Soc 1956, 78:5430-5433.
22. Klärner F-GG, Jones M, Magid RM. William von Eggers doering's many research achievements during the first 65 years of his career in chemistry. Acc Chem Res 2009, 42:169-181.
23. Merceron-Saffon N, Baceiredo A, Gornitzka H, Bertrand G. Synthesis of carbenes through substitution reactions at a carbene center. Science 2003, 301:1223-1225.
24. Canac Y, Conejero S, Donnadieu B, Schoeller WW, Bertrand G. Persistent (amino)(silyl)carbenes. J Am Chem Soc 2005, 127:7312-7313.
25. Canac Y, Conejero S, Soleilhavoup M, Donnadieu B, Bertrand G. Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes. J Am Chem Soc 2006, 128:459-464.
26. Vignolle J, Donnadieu B, Bourissou D, Bertrand G. An unusual norcaradiene/tropylium rearrangement from a persistent amino-phosphonio-carbene. Tetrahedron Lett 2007, 48:685-687.
27. Canac Y, Lepetit C, Abdalilah M, Duhayon C, Chauvin R. Diaminocarbene and phosphonium ylide ligands: a systematic comparison of their donor character. J Am Chem Soc 2008, 130:8406-8413.
28. Hoffmann RW, Reiffen M. Carben-Reaktionen, VII: über das nucleophile Verhalten von Dimethoxycarben. Chem Ber 1976, 109:2565-2571.
29. Moss RA, Wlostowski M, Shen S, Krogh-Jespersen K, Matro A. Dimethoxycarbene: direct observation of an archetypal nucleophilic carbene. J Am Chem Soc 1988, 110:4443-4444.
30. Reisenauer HP, Romanski J, Mloston G, Schreiner PR. Dimethoxycarbene: conformational analysis of a reactive intermediate. Eur J Org Chem 2006, 2006:4813-4818.
31. Schreiner PR, Reisenauer HP, Romanski J, Mloston G. [1, 3]Dithian-2-ylidene. Angew Chem Int Edit 2006, 45:3989-3992.
32. Reisenauer HP, Maier G, Riemann A, Hoffmann RW. Cyclopropenylidene. Angew Chem Int Edit 1984, 23:641-641.
33. Mieusset J-L, Brinker UH. The nature and extent of π-stabilization within foiled carbenes. J Am Chem Soc 2006, 128:15843-15850.
34. Mieusset J-L, Abraham M, Brinker UH. Carbene-alkene complexes between a nucleophilic carbene and electron-poor alkenes. J Am Chem Soc 2008, 130:14634-14639.
35. Brinker UH, Bespokoev AA, Reisenauer HP, Schreiner PR. Conformations and reactions of bicyclo[3.2.1]oct-6-en-8-ylidene. J Org Chem 2012, 77:3800-3807.
36. Mieusset J-LL, Brinker UH. The carbene reactivity surface: a classification. J Org Chem 2008, 73:1553-1558.
37. Enders D, Niemeier O, Henseler A. Organocatalysis by N-heterocyclic carbenes. Chem Phys Lett 2007, 107:5606-5655.
38. Marion N, Díez-González S, Nolan SP. N-heterocyclic carbenes as organocatalysts. Angew Chem Int Edit 2007, 46:2988-3000.
39. Dröge T, Glorius F. The measure of all rings-N-heterocyclic carbenes. Angew Chem Int Edit 2010, 49:6940-6952.
40. Maji B, Breugst M, Mayr H. N-heterocyclic carbenes: organocatalysts with moderate nucleophilicity but extraordinarily high Lewis basicity. Angew Chem Int Edit 2011, 50:6915-6919.
41. Breslow R. On the mechanism of thiamine action. IV.1 Evidence from studies on model systems. J Am Chem Soc 1958, 80:3719-3726.
42. Maier G, Endres J, Reisenauer HP. 2, 3-Dihydrothiazol-2-ylidene. Angew Chem Int Edit 1997, 36:1709-1712.
43. Wang Y, Quillian B, Wei P, Wannere CS, Xie Y, King RB, Schaefer HF, Schleyer PvR, Robinson GH. A stable, neutral diborene containing a B=B double bond. J Am Chem Soc 2007, 129:12412-12413.
44. 2(idipp): a stable N-heterocyclic carbene adduct of dibromosilylene. Angew Chem Int Edit 2009, 48:5687-5690.
45. Xiong Y, Yao S, Driess M. An isolable NHC-supported silanone. J Am Chem Soc 2009, 131:7562-7563.
46. 2) and its reactivity toward alkyne: synthesis of stable disilacyclobutene. J Am Chem Soc 2010, 132:1123-1126.
47. Walton JC, Brahmi MM, Fensterbank L, Lacóte E, Malacria M, Chu Q, Ueng S-H, Solovyev A, Curran DP. EPR studies of the generation, structure, and reactivity of n-heterocyclic carbene borane radicals. J Am Chem Soc 2010, 132:2350-2358.
48. 2)=E (E=O, S, Se, Te). Chem Eur J 2010, 16:1281-1288.
49. Inoue S, Wang W, Präsang C, Asay M, Irran E, Driess M. An ylide-like phosphasilene and striking formation of a 4π-electron, resonance-stabilized 2, 4-disila-1, 3-diphosphacyclobutadiene. J Am Chem Soc 2011, 133:2868-2871.
50. Wang Y, Xie Y, Abraham MY, Wei P, Schaefer HF, Schleyer PvR, Robinson GH. Anionic N-heterocyclic dicarbene-borane binuclear complexes. Organometallics 2011, 30:1303-1306.
51. Wang Y, Xie Y, Wei P, King RB, Schaefer HF, Schleyer PvR, Robinson GH. Carbene-stabilized diphosphorus. J Am Chem Soc 2008, 130:14970-14971.
52. Abraham MY, Wang Y, Xie Y, Wei P, Schaefer HF, Schleyer PvR, Robinson GH. Carbene stabilization of diarsenic: from hypervalency to allotropy. Chem Eur J 2010, 16:432-435.
53. Wang Y, Xie Y, Wei P, King RB, Schaefer HF, Schleyer PvR, Robinson GH. A stable silicon(0) compound with a Si=Si double bond. Science 2008, 321:1069-1071.
54. Abraham MY, Wang Y, Xie Y, Wei P, Schaefer HF, Schleyer PvR, Robinson GH. Cleavage of carbene-stabilized disilicon. J Am Chem Soc 2011, 133:8874-8876.
55. Thaddeus P, Gottlieb CA, Mollaaghababa R, Vrtilek JM. Free carbenes in the interstellar gas. J Chem Soc Faraday Trans 1993, 89:2125-2129.
56. Bohme DK. Ionic origins of carbenes in space. Nature 1986, 319:473-474.
57. Ohishi M, Suzuki H, Ishikawa S-I, Yamada C, Kanamori H, Irvine WM, Brown RD, Godfrey PD, Kaifu N. Detection of a new carbon-chain molecule, CCO. Astrophys J Lett 1991, 380:L39-L42.
58. Hollis JM, Jewell PR, Lovas FJ. Confirmation of interstellar methylene. Astrophys J 1995, 438:259-264.
59. Irvine WM, Ziurys LM, Avery LW, Matthews HE, Friber P. Newly Detected Molecules in Dense Interstellar Clouds. Astrophys. Comm. Lett. 1998, 26:167-180.
60. Fossé D, Cernicharo J, Gerin M, Cox P. Molecular carbon chains and rings in TMC-1. Astrophys J 2001, 552:168.
61. 2) and the singlet-triplet splitting. J Chem Phys 1986, 85:3724-3731.
62. 2 configurations. Rev Mod Phys 1960, 32:305-307.
63. Harrison JF, Allen LC. Electronic Structure of Methylene. J Am Chem Soc 1969, 91:807-823.
64. Herzberg G, Shoosmith J. Spectrum and structure of the free methylene radical. Nature 1959, 183:1801-1802.
65. Herzberg G. The Bakerian lecture. The spectra and structures of free methyl and Free methylene. Proc R Soc Lond A 1961, 262:291-317.
66. Bender CF, Schaefer HF. New theoretical evidence for the nonlinearity of the triplet ground state of methylene. J Am Chem Soc 1970, 92:4984-4985.
67. Fokin AA, Gerbig D, Schreiner PR. σ/σ- and π/π-interactions are equally important: multilayered graphanes. J Am Chem Soc 2011, 133:20036-20039.
68. Goerigk L, Grimme S. A general database for main group thermochemistry, kinetics, and noncovalent interactions- assessment of common and reparameterized (meta-) GGA density functionals. J Chem Theory Comput 2010, 6:107-126.
69. Goerigk L, Grimme S. A thorough benchmark of density functional methods for general main group thermochemistry, kinetics, and noncovalent interactions. Phys Chem Chem Phys 2011, 13:6670-6688.
70. Goerigk L, Kruse H, Grimme S. Benchmarking density functional methods against the s66 and s66x8 datasets for non-covalent interactions. ChemPhysChem 2011, 12:3421-3433.
71. Grimme S. Seemingly simple stereoelectronic effects in alkane isomers and the implications for Kohn-Sham density functional theory. Angew Chem Int Edit 2006, 45:4460-4464.
72. Grimme S. Density functional theory with london dispersion corrections. WIREs Comput Mol Sci 2011, 1:211-228.
73. Grimme S, Antony J, Ehrlich S, Krieg H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys 2010, 132:154104.
74. Grimme S, Ehrlich S, Goerigk L. Effect of the damping function in dispersion corrected density functional theory. J Comput Chem 2011, 32:1456-1465.
75. Korth M, Grimme S. Mindless DFT benchmarking. J Chem Theory Comput 2009, 5:7764-7776.
76. Schreiner PR. Relative energy computations with approximate density functional theory-a caveat! Angew Chem Int Edit 2007, 46:4217-4219.
77. Schreiner PR, Fokin AA, Pascal RA, de Meijere A. Many density functional theory approaches fail to give reliable large hydrocarbon isomer energy differences. Org Lett 2006, 8:3635-3638.
78. 1) by broken-symmetry method. J Phys Chem A 2009, 113:15041-15046.
79. Lee H, Miyamoto Y, Tateyama Y. Excited state carbene formation from UV irradiated diazomethane. J Org Chem 2009, 74:562-567.
80. Miller DM, Schreiner PR, Schaefer HF. Singlet methylcarbene: an elusive intermediate of the thermal decomposition of diazoethane and methyldiazirine. J Am Chem Soc 1995, 117:4137-4143.
81. Lasorne B, Worth GA, Robb MA. Excited-state dynamics. WIREs Comput Mol Sci 2011, 1:460-475.
82. Wilsey S, Houk KN. "H/Vinyl" and "Alkyl/Vinyl" conical intersections leading to carbene formation from the excited states of cyclohexene and norbornene. J Am Chem Soc 2002, 124:11182-11190.
83. Gleiter R, Hoffmann R. Stabilizing a singlet methylene. J Am Chem Soc 1968, 90:5457-5460.
84. Mieusset J-L, Schrems A, Abraham M, Arion VB, Brinker UH. Stepwise insertion of carbenes into C-H Bonds: the case of foiled carbenes. Tetrahedron 2009, 65:765-770.
85. Mieusset J-L, Brinker UH. Foiled carbenes revisited: when σ-stabilization surpasses π-stabilization. J Org Chem 2007, 72:263-268.
86. 8 molecule with a pyramidally coordinated carbon. J Org Chem 2006, 71:6975-6982.
87. Seburg RA, Patterson EV, McMahon RJ. Structure of triplet propynylidene (HCCCH) as probed by IR, UV/Vis, and EPR spectroscopy of isotopomers. J Am Chem Soc 2009, 131:9442-9455.
88. DePinto JT, deProphetis WA, Menke JL, McMahon RJ. Triplet 1, 3-diphenylpropynylidene (Ph-C-C-C-Ph). J Am Chem Soc 2007, 129:2308-2315.
89. Bowling NP, Halter RJ, Hodges JA, Seburg RA, Thomas PS, Simmons CS, Stanton JF, McMahon RJ. Reactive carbon-chain molecules: synthesis of 1-diazo-2, 4-pentadiyne and spectroscopic characterization of triplet pentadiynylidene (H-C≡C-C-C≡C-H). J Am Chem Soc 2006, 128:3291-3302.
90. Boganov SE, Faustov VI, Shavrin KN, Gvozdev VD, Promyslov VM, Egorov MP, Nefedov OM. A highly delocalized triplet carbene, 5-methylhexa-1, 2, 4-triene-1, 3-diyl: matrix ir identification, structure, and reactions. J Am Chem Soc 2009, 131:14688-14698.
91. Noller B, Poisson L, Maksimenka R, Gobert O, Fischer I, Mestdagh JM. Ultrafast dynamics of isolated phenylcarbenes followed by femtosecond time-resolved velocity map imaging. J Phys Chem A 2009, 113:3041-3050.
92. Woodcock HL, Moran D, Brooks BR, Schleyer PvR, Schaefer HF. Carbene stabilization by aryl substituents. Is bigger better? J Am Chem Soc 2007, 129:3763-3770.
93. Moss RA, Zheng F, Fedé J-MM, Johnson LA, Sauers RR. Solvent-equilibrated ion pairs from carbene fragmentation reactions. J Am Chem Soc 2004, 126:12421-12431.
94. Moss RA, Sauers RR, Zheng F, Fu X, Bally T, Maltsev A. Rearrangements concerted with fragmentation of cyclopropylmethoxychlorocarbene and cyclobutoxychlorocarbene in hydrocarbon solvents and Ar matrices. J Am Chem Soc 2004, 126:8466-8476.
95. Moss RA, Ma Y, Sauers RR, Madni M. Nortricyclyl-norbornenyl cation system accessed by carbene fragmentation. J Org Chem 2004, 69:3628-3634.
96. Aue DH. Carbocations. WIREs Comput Mol Sci 2011, 1:487-508.
97. Moss RA, Tian J, Sauers RR, Krogh-Jespersen K. Tracking "invisible" alkylchlorocarbenes by their σ→p absorptions: dynamics and solvent interactions. J Am Chem Soc 2007, 129:10019-10028.
98. Moss RA, Wang L, Weintraub E, Krogh-Jespersen K. The solvation of carbenes: π and O-ylidic complexes of p-nitrophenylchlorocarbene. J Phys Chem A 2008, 112:4651-4659.
99. Moss RA, Wang L, Odorisio CM, Zhang M, Krogh-Jespersen K. Solvation of dichlorocarbene: complexation with aryl ethers. J Phys Chem A 2010, 114:209-217.
100. Mieusset J-L, Brinker UH. Toward selective reactions with C-H bonds: a rationale for the regio- and stereochemistry of dichlorocarbene insertions into cyclic hydrocarbons. J Org Chem 2007, 72:10211-10219.
101. Rablen PR, Paiz AA, Thuronyi BW, Jones M. Computational investigation of the mechanism of addition of singlet carbenes to bicyclobutanes. J Org Chem 2009, 74:4252-4261.
102. Gao X, Ohtsuka Y, Ishimura K, Nagase S. Mechanism and dynamic correlation effects in cycloaddition reactions of singlet difluorocarbene to alkenes and disilene. J Phys Chem A 2009, 113:9852-9860.
103. Buron C, Tippmann EM, Platz MS. Generation and characterization of new fluoro-substituted carbenes. J Phys Chem A 2004, 108:1033-1041.
104. 2]. J Fluorine Chem 2009, 130:836-845.
105. Li Q, Wang Y, Liu Z, Li W, Cheng J, Gong B, Sun J. An unconventional halogen bond with carbene as an electron donor: an ab initio study. Chem Phys Lett 2009, 469:48-51.
106. Alabugin IV, Gilmore KM, Peterson PW. Hyperconjugation. WIREs Comput Mol Sci 2011, 1:109-141.
107. Moss RA, Sauers RR, Sheridan RS, Tian J, Zuev PS. Carbon tunneling in the ring expansion of noradamantylchlorocarbene. J Am Chem Soc 2004, 126:10196-10197.
108. Isaacson AD, Truhlar DG, Rai SN, Steckler R, Hancock GC, Garrett BC, Redmon MJ. POLYRATE: a general computer program for variational transition state theory and semiclassical tunneling calculations of chemical reaction rates. Comput Phys Commun 1987, 47:91-102.
109. Truhlar DG, Gordon MS. From force fields to dynamics: classical and quantal paths. Science 1990, 249:491-498.
110. Steckler R, Hu W-P, Liu Y-P, Lynch GC, Garrett BC, Isaacson AD, Melissas VS, Lu D, Truong TN, Rai SN, et al. POLYRATE 6.5: a new version of a computer program for the calculation of chemical reaction rates for polyatomics. Comput Phys Commun 1995, 88:341-343.
111. Cattoën X, Miqueu K, Gornitzka H, Bourissou D, Bertrand G. Evidence for radical fragmentations from persistent singlet carbenes. J Am Chem Soc 2005, 127:3292-3293.
112. Kvaskoff D, Bednarek P, Wentrup C. 2-pyridylnitrene and 3-pyridazylcarbene and their relationship via ring-expansion, ring-opening, ring-contraction, and fragmentation. J Org Chem 2010, 75:1600-1611.
113. Frenking G, Tonner R. Carbodicarbenes-divalent carbon(0) compounds exhibiting carbon-carbon donor-acceptor bonds. WIREs Comput Mol Sci 2011, 1:869-878.
114. Illa O, Álvarez-Larena Á, Baceiredo A, Branchadell V, Ortuño RM. Highly stereoselective and easy synthesis of enantiopure phosphoranyl oxiranes. Tetrahedron: Asymmetry 2007, 18:2617-2620.
115. Lecea B, Ayerbe M, Arrieta A, Cossío FP, Branchadell V, Ortuño RM, Baceiredo A. Theoretical study on the mechanism of the [2+1] thermal cycloaddition between alkenes and stable singlet (phosphino)(silyl)carbenes. J Org Chem 2007, 72:357-366.
116. Reid DL, Hernandez-Trujillo J, Warkentin J. A theoretical study of hydroxycarbene as a model for the homolysis of oxy-and dioxycarbenes. J Phys Chem A 2000, 104:3398-3405.
117. Reid DL, Warkentin J. Homolysis of Allyloxy(hydroxy)carbene. A density functional theory and ab initio study. J Chem Soc Perkin Trans 2 2000:1980-1983.
118. Czardybon W, Warkentin J, Werstiuk NH. Computational study of the thermal rearrangement of acetoxy(methoxy)carbene. J Phys Org Chem 2005, 18:486-490.
119. Loncke PG, Peslherbe GH. Mechanisms of intramolecular rearrangements of cyclic siloxycarbenes. J Phys Chem A 2004, 108:4694-4706.
120. Loncke PG, Peslherbe GH. A theoretical investigation of the decarbonylation of methoxy(siloxy)carbene. J Phys Chem A 2004, 108:6206-6215.
121. Bogdanova A, Popik VV. Experimental and theoretical analysis of the photochemistry and thermal reactivity of ethyl diazomalonate and its diazirino isomer. The role of molecular geometry in the decomposition of diazocarbonyl compounds. J Am Chem Soc 2004, 126:11293-11302.
122. Schreiner PR, Reisenauer HP. Spectroscopic identification of dihydroxycarbene. Angew Chem Int Edit 2008, 47:7071-7074.
123. Schreiner PR, Reisenauer HP. The "non-reaction" of ground-state triplet carbon atoms with water revisited. ChemPhysChem 2006, 7:880-885.
124. Gerbig D, Ley D, Reisenauer HP, Schreiner PR. Intramolecular hydroxycarbene C-H-insertion: the curious case of (o-methoxyphenyl)hydroxycarbene. Beilstein J Org Chem 2010, 6:1061-1069.
125. 4S energy surface: a computational study. J Am Chem Soc 2001, 123:9418-9425.
126. Schreiner PR, Reisenauer HP, Romanski J, Mloston G. A formal carbon-sulfur triple bond: H-C≡S-O-H. Angew Chem Int Edit 2009, 48:8133-8136.
127. Brandhorst K, Grunenberg J. Efficient computation of compliance matrices in redundant internal coordinates from Cartesian Hessians for nonstationary points. J Chem Phys 2010, 132:184101.
128. Rzepa HS. Nature of the carbon-sulfur bond in the species H-CS-OH. J Chem Theory Comput 2010, 7:97-102.
129. Schoeller WW, Frey GD, Bertrand G. Tuning the nucleophilicity in cyclopropenylidenes. Chem Eur J 2008, 14:4711-4718.
130. Kassaee MZ, Ghambarian M, Musavi SM, Shakib FA, Momeni MR. A theoretical investigation into dimethylcarbene and its diamino and diphosphino analogs: effects of cyclization and unsaturation on the stability and multiplicity. J Phys Org Chem 2009, 22:919-924.
131. Kassaee MZ, Shakib FA, Momeni MR, Ghambarian M, Musavi SM. Carbenes with reduced heteroatom stabilization: a computational approach. J Org Chem 2010, 75:2539-2545.
132. Gronert S, Keeffe JR, More O'Ferrall RA. Correlations between carbene and carbenium stability: ab initio calculations on substituted phenylcarbenes, nonbenzenoid arylcarbenes, heteroatom-substituted carbenes, and the corresponding carbocations and hydrogenation products. J Org Chem 2009, 74:5250-5259.
133. Gronert S, Keeffe JR, More O'Ferrall RA. Stabilities of carbenes: independent measures for singlets and triplets. J Am Chem Soc 2011, 133:3381-3389.
134. Graham DC, Cavell KJ, Yates BF. Dimerization mechanisms of heterocyclic carbenes. J Phys Org Chem 2005, 18:298-309.
135. Goedecke C, Leibold M, Siemeling U, Frenking G. When does carbonylation of carbenes yield ketenes? A theoretical study with implications for synthesis. J Am Chem Soc 2011, 133:3557-3569.
136. Jabłoński M, Palusiak M. Divalent carbon atom as the proton acceptor in hydrogen bonding. Phys Chem Chem Phys 2009, 11:5711-5719.
137. 2: combined matrix-ir and CCSD(T) identification, and the role of the open-shell singlet state. Org Lett 2004, 6:1163-1166.
138. Nemirowski A, Reisenauer HP, Romanski J, Mloston G, Schreiner PR. Prototypical triplet alkyl phosphonatocarbenes. J Phys Chem A 2008, 112:13244-13248.
139. Gräfenstein J, Cremer D. Can density functional theory describe multi-reference systems? Investigation of carbenes and organic biradicals. Phys Chem Chem Phys 2000, 2:2091-2103.
140. Hajgató B, Nguyen HMT, Veszpremi T, Nguyen MT. Triplet-singlet energy gaps in iodo-carbenes (I-C-X): remarkable discrepancy between theory and experiment. Phys Chem Chem Phys 2000, 2:5041-5045.
141. Császár AG, Allen WD, Schaefer HF. In pursuit of the ab initio limit for conformational energy prototypes. J Chem Phys 1998, 108:9751-9764.
142. 2 from ab initio molecular orbital theory. J Phys Chem A 2006, 110:1968-1974.
143. 2 carbenes. J Phys Chem A 2009, 113:12447-12453.
144. 2CCC). J Phys Chem A 2010, 114:9782-9787.
145. Matus MH, Nguyen MT, Dixon DA. Heats of formation and singlet-triplet separations of hydroxymethylene and 1-hydroxyethylidene. J Phys Chem A 2006, 110:8864-8871.
146. Schreiner PR, Reisenauer HP, Pickard FC, Simmonett AC, Allen WD, Mátyus E, Császár AG. Capture of hydroxymethylene and its fast disappearance through tunnelling. Nature 2008, 453:906-909.
147. Mahapatra US, Datta B, Mukherjee D. A size-consistent state-specific multireference coupled cluster theory: formal developments and molecular applications. J Chem Phys 1999, 110:6171-6188.
148. Schreiner PR, Reisenauer HP, Ley D, Gerbig D, Wu C-H, Allen WD. Methylhydroxycarbene: tunneling control of a chemical reaction. Science 2011, 332:1300-1303.
149. Carpenter BK. Taking the high road and getting there before you. Science 2011, 332:1269-1270.
150. Rehbein J, Carpenter BK. Do we fully understand what controls chemical selectivity? Phys Chem Chem Phys 2011, 13:20906-20922.
151. Ley D, Gerbig D, Schreiner PR. Durch die Wand-Tunnelkontrolle chemischer Reaktionen. Nachrichten Chem 2011, 59:1139-1141.
152. Gerbig D, Reisenauer HP, Wu C-H, Ley D, Allen WD, Schreiner PR. Phenylhydroxycarbene. J Am Chem Soc 2010, 132:7273-7275.
153. Ley D, Gerbig D, Wagner JP, Reisenauer HP, Schreiner PR. Cyclopropylhydroxycarbene. J Am Chem Soc 2011, 133:13614-13621.
154. Gerbig D, Ley D, Schreiner PR. Light- and heavy-atom tunneling in rearrangement reactions of cyclopropylcarbenes. Org Lett 2011, 13:3526-3529.
155. Denis PA, Iribarne F. Theoretical investigation of carbon-sulfur triple bonds. Chem Eur J 2011, 17:1979-1987.
156. 2CS into cis and trans FCSF. Chem Commun 2009:5162-5164.
157. 3: two solid-state structures and reactivity as a carbene. J Am Chem Soc 1992, 114:9465-9469.
158. 3. Angew Chem Int Edit 1988, 27:1534-1536.
159. Evangelista FA, Allen WD, Schaefer HF. High-order excitations in state-universal and state-specific multireference coupled cluster theories: model systems. J Chem Phys 2006, 125:154113.
160. Evangelista FA, Allen WD, Schaefer HF. Coupling term derivation and general implementation of state-specific multireference coupled cluster theories. J Chem Phys 2007, 127:024102.
161. Bhaskaran-Nair K, Demel O, Pittner J. Multireference state-specific Mukherjee's coupled cluster method with noniterative triexcitations. J Chem Phys 2008, 129:184105.
162. Čížek J. On the correlation problem in atomic and molecular systems. calculation of wavefunction components in Ursell-type expansion using quantum-field theoretical methods. J Chem Phys 1966, 45:4256-4266.
163. Bartlett RJ, Purvis GD. Many-body perturbation theory, coupled-pair many-electron theory, and the importance of quadruple excitations for the correlation problem. Int J Quantum Chem 1978, 14:561-581.
164. Purvis GD, Bartlett RJ. A full coupled-cluster singles and doubles model: the inclusion of disconnected triples. J Chem Phys 1982, 76:1910-1918.
165. Pople JA, Head-Gordon M, Raghavachari K. Quadratic configuration interaction. a general technique for determining electron correlation energies. J Chem Phys 1987, 87:5968-5975.
166. Scuseria GE, Janssen CL, Schaefer HF. An efficient reformulation of the closed-shell coupled cluster single and double excitation (CCSD) equations. J Chem Phys 1988, 89:7382-7387.
167. Raghavachari K, Trucks GW, Pople JA, Head-Gordon M. A fifth-order perturbation comparison of electron correlation theories. Chem Phys Lett 1989, 157:479-483.
168. Scuseria GE, Schaefer HF. Is coupled cluster singles and doubles (CCSD) more computationally intensive than quadratic configuration interaction (QCISD)? J Chem Phys 1989, 90:3700-3703.
169. Noga J, Bartlett RJ. The full CCSDT model for molecular electronic structure. J Chem Phys 1987, 86:7041-7050.
170. Scuseria GE, Schaefer HF. A new implementation of the full CCSDT model for molecular electronic structure. Chem Phys Lett 1988, 152:382-386.
171. Kucharski SA, Bartlett RJ. An efficient way to include connected quadruple contributions into the coupled cluster method. J Chem Phys 1998, 108:9221-9226.
172. Schlegel HB. Geometry optimization. WIREs Comput Mol Sci 2011, 1:790-809.
173. Gerenkamp M, Grimme S. Spin-component scaled second-order Møller-Plesset perturbation theory for the calculation of molecular geometries and harmonic vibrational frequencies. Chem Phys Lett 2004, 392:229-235.
174. Grimme S. Accurate calculation of the heats of formation for large main group compounds with spin-component scaled MP2 methods. J Phys Chem A 2005, 109:3067-3077.
175. Antony J, Grimme S. Is spin-component scaled second-order Møller-Plesset perturbation theory an appropriate method for the study of noncovalent interactions in molecules? J Phys Chem A 2007, 111:4862-4868.
176. Takatani T, David Sherrill C. Performance of spin-component-scaled Møller-Plesset theory (SCS-MP2) for potential energy curves of noncovalent interactions. Phys Chem Chem Phys 2007, 9:6106-6114.
177. Fink RF. Spin-component-scaled Møller-Plesset (SCS-MP) perturbation theory: a generalization of the MP approach with improved properties. J Chem Phys 2010, 133:174113.
178. Zhao Y, Truhlar DG. Density functionals with broad applicability in chemistry. Acc Chem Res 2008, 41:157-167.
179. Zhao Y, Truhlar DG. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06 functionals and twelve other functionals. Theor Chem Acc 2008, 120:215-241.
180. Zhao Y, Truhlar DG. Exploring the limit of accuracy of the global hybrid meta density functional for main-group thermochemistry, kinetics, and noncovalent interactions. J Chem Theory Comput 2008, 4:1849-1868.
181. Zheng J, Zhao Y, Truhlar DG. The DBH24/08 database and its use to assess electronic structure model chemistries for chemical reaction barrier heights. J Chem Theory Comput 2009, 5:808-821.
182. Zhao Y, Truhlar DG. Density functional theory for reaction energies: test of meta and hybrid meta functionals, range-separated functionals, and other high-performance functionals. J Chem Theory Comput 2011, 7:669-676.
183. Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988, 37:785-789.
184. Miehlich B, Savin A, Stoll H, Preuss H. Results obtained with the correlation energy density functionals of Becke and Lee, Yang and Parr. Chem Phys Lett 1989, 157:200-206.
185. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993, 98:5648-5652.
186. Perdew JP, Chevary JA, Vosko SH, Jackson KA, Pederson MR, Singh DJ, Fiolhais C. Atoms, molecules, solids, and surfaces: applications of the generalized gradient approximation for exchange and correlation. Phys Rev B 1992, 46:6671-6687.
187. Perdew JP, Chevary JA, Vosko SH, Jackson KA, Pederson MR, Singh DJ, Fiolhais C. Erratum: atoms, molecules, solids, and surfaces: applications of the generalized gradient approximation for exchange and correlation. Phys Rev B 1993, 48:4978.
188. Perdew JP, Burke K, Wang Y. Generalized gradient approximation for the exchange-correlation hole of a many-electron system. Phys Rev B 1996, 54:16533-16539.
189. Tajti A, Szalay PG, Császár AG, Kállay M, Gauss J, Valeev EF, Flowers BA, Vázquez J, Stanton JF. HEAT: high accuracy extrapolated ab initio thermochemistry. J Chem Phys 2004, 121:11599-11613.
190. Curtiss LA, Redfern PC, Raghavachari K. Gaussian-4 theory. J Chem Phys 2007, 126:084108.
191. Martin JML, de Oliveira G. Towards Standard methods for benchmark quality ab initio thermochemistry-W1 and W2 theory. J Chem Phys 1999, 111:1843-1856.
192. Zhao Y, Schultz NE, Truhlar DG. Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theory Comput 2006, 2:364-382.
193. Wheeler SE, Houk KN. Integration grid errors for meta-GGA-predicted reaction energies: origin of grid errors for the M06 suite of functionals. J Chem Theory Comput 2010, 6:395-404.
194. Wheeler SE, Houk KN, Schleyer PvR, Allen WD. A hierarchy of homodesmotic reactions for thermochemistry. J Am Chem Soc 2009, 131:2547-2560.
195. Cremer D. Møller-Plesset perturbation theory: from small molecule methods to methods for thousands of atoms. WIREs Comput Mol Sci 2011, 1:509-530.
196. Alecu IM, Zheng J, Zhao Y, Truhlar DG. Computational thermochemistry: scale factor databases and scale factors for vibrational frequencies obtained from electronic model chemistries. J Chem Theory Comput 2010, 6:2872-2887.
197. Johnson RD, Irikura KK, Kacker RN, Kessel Rd. Scaling factors and uncertainties for ab initio anharmonic vibrational frequencies. J Chem Theory Comput 2010, 6:2822-2828.
198. Laury ML, Boesch SE, Haken I, Sinha P, Wheeler RA, Wilson AK. Harmonic vibrational frequencies: scale factors for pure, hybrid, hybrid meta, and double-hybrid functionals in conjunction with correlation consistent basis sets. J Comput Chem 2011, 32:2339-2347.