메뉴 건너뛰기




Volumn 133, Issue 4, 2011, Pages 780-789

Hydrolysis of lmidazole-2-ylidenes

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO MOLECULAR DYNAMICS SIMULATION; APROTIC; AROMATIC STABILIZATION; CARBENES; COMPUTATIONAL STUDIES; DIRECT REACTIONS; DYNAMIC EQUILIBRIA; HYDROLYSIS PRODUCTS; HYDROXIDE IONS; IMIDAZOL; IMIDAZOLIUM; ION PAIRS; IR SPECTROSCOPY; MECHANISTIC STUDIES; RING-OPENED PRODUCTS; SOLVENT STABILIZATION; SOLVENT SYSTEM; STABLE SOLUTIONS; WATER COMPLEXES; WATER CONCENTRATIONS; WATER MOLECULE;

EID: 79851502857     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103578y     Document Type: Article
Times cited : (131)

References (75)
  • 19
    • 36549000812 scopus 로고    scopus 로고
    • Recently, different imidazole-2-ylidene derivatives have been dissolved in silicone oils, and this mixture has been found to be stable in air for months. This finding has been rationalized considering a stabilizing effect by formation of pentacoordinate silicon compounds, see the following
    • Recently, different imidazole-2-ylidene derivatives have been dissolved in silicone oils, and this mixture has been found to be stable in air for months. This finding has been rationalized considering a stabilizing effect by formation of pentacoordinate silicon compounds, see the following: Bonette, F.; Kato, T.; Destarac, M.; Mignani, G.; Cossío, F. P.; Baceiredo, A. Angew. Chem.. Int. Ed. 2007, 46, 8632-8635.
    • (2007) Angew. Chem.. Int. Ed. , vol.46 , pp. 8632-8635
    • Bonette, F.1    Kato, T.2    Destarac, M.3    Mignani, G.4    Cossío, F.P.5    Baceiredo, A.6
  • 24
    • 33750386593 scopus 로고
    • Insertion of carbenes into O-H bonds is also known with alcohols see ref la, and in the case of highly stabilized carbenes this reaction was found to be reversible. See the following
    • Insertion of carbenes into O-H bonds is also known with alcohols (see ref la), and in the case of highly stabilized carbenes this reaction was found to be reversible. See the following: Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Anrew. Chem.. Int. Ed. End. 1995, 34, 1021.
    • (1995) Anrew. Chem.. Int. Ed. End , vol.34 , pp. 1021
    • Enders, D.1    Breuer, K.2    Raabe, G.3    Runsink, J.4    Teles, J.H.5    Melder, J.P.6    Ebel, K.7    Brode, S.8
  • 26
    • 0029875262 scopus 로고    scopus 로고
    • Imidazole-2-ylidene has aromatic properties, see the following: a Boeme, C.; Frenking, G
    • Imidazole-2-ylidene has aromatic properties, see the following: (a) Boeme, C.; Frenking, G. J. Am. Chem. Soc. 1996, 118, 2039-2046.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2039-2046
  • 32
    • 0016270590 scopus 로고
    • It is worthy to note that, in the case of thiazolium salts apart from the proton exchange, the addition of the hydroxide to the C 2, followed by the ring opening, has also been observed, and has also been suggested as the possible reason for the facile absorption of thiamine into the cells. See the following: a
    • It is worthy to note that, in the case of thiazolium salts apart from the proton exchange, the addition of the hydroxide to the C (2), followed by the ring opening, has also been observed, and has also been suggested as the possible reason for the facile absorption of thiamine into the cells. See the following: (a) Duclos, J. M.; Haake, P. Biochemistry 1974, 13, 5358.
    • (1974) Biochemistry , vol.13 , pp. 5358
    • Duclos, J.M.1    Haake, P.2
  • 45
    • 61649105593 scopus 로고    scopus 로고
    • This methodology has recently been successfully used to model the hydrolysis of silyl-ethers. For more detailed discussion of the model, and the accuracy of the B3LYP method compared to MP2, see the following
    • This methodology has recently been successfully used to model the hydrolysis of silyl-ethers. For more detailed discussion of the model, and the accuracy of the B3LYP method compared to MP2, see the following: Terleczky, P.; Nyulászi, L. J. Phys. Chem. A 2009, 113, 1096-1104.
    • (2009) J. Phys. Chem. A , vol.113 , pp. 1096-1104
    • Terleczky, P.1    Nyulászi, L.2
  • 47
    • 4243539377 scopus 로고
    • RI-MP2 and RI-B97-D single point energies have been calculated by the Turbomole 5.10 program package
    • (b) RI-MP2 and RI-B97-D single point energies have been calculated by the Turbomole 5.10 program package: Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 165.
    • (1989) Chem. Phys. Lett. , vol.162 , pp. 165
    • Ahlrichs, R.1    Bär, M.2    Häser, M.3    Horn, H.4    Kölmel, C.5
  • 48
    • 33746563448 scopus 로고    scopus 로고
    • z.ast; single point energies have been calculated by the QjChem 3.2 program package "Advances in methods and algorithms in a modern quantum chemistry program package"
    • z.ast; single point energies have been calculated by the QjChem 3.2 program package "Advances in methods and algorithms in a modern quantum chemistry program package": Y. Shao, L.; et al. Phys. Chem. Chem. Phys. 2006, 8, 3172.
    • (2006) Phys. Chem. Chem. Phys. , vol.8 , pp. 3172
    • Shao, Y.L.1
  • 54
    • 77950417434 scopus 로고    scopus 로고
    • Similar H-bonded structures with alcohols and amines has been investigated computationally, see the following
    • (a) Similar H-bonded structures with alcohols and amines has been investigated computationally, see the following: De Sarkar, S.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190-1191.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 1190-1191
    • De Sarkar, S.1    Grimme, S.2    Studer, A.3
  • 55
    • 0037090999 scopus 로고    scopus 로고
    • Similar H-bonded structure between diphenylamine and an imidazole-2-ylidene has been characterized by x-ray crystallography, see the following.
    • (b) Similar H-bonded structure between diphenylamine and an imidazole-2-ylidene has been characterized by x-ray crystallography, see the following.: Cowan, J. A.; Clyburne, J. A. C.; Davidson, M. G.; Harris, R L. W.; Howard, J. A. K.; Kupper, P.; Leech, M. A; Richards, S. P. Angew. Chem., Int. Ed. 2002, 41, 1432.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1432
    • Cowan, J.A.1    Clyburne, J.A.C.2    Davidson, M.G.3    Harris, R.L.W.4    Howard, J.A.K.5    Kupper, P.6    Leech, M.A.7    Richards, S.P.8
  • 57
    • 34247543841 scopus 로고    scopus 로고
    • Similar insertion with comparable barrier has been suggested in case of the reaction of a cyclic alkyl amino carbene and ammonia, see the following
    • Similar insertion with comparable barrier has been suggested in case of the reaction of a cyclic (alkyl) (amino) carbene and ammonia, see the following: Frey, G. D.; Lavallo, V.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2007, 316, 439.
    • (2007) Science , vol.316 , pp. 439
    • Frey, G.D.1    Lavallo, V.2    Donnadieu, B.3    Schoeller, W.W.4    Bertrand, G.5
  • 58
    • 79851476259 scopus 로고    scopus 로고
    • -1 barrier is likely to proceed via a bimolecular process and with a small barrier. For more information, also see Supporting Information
    • -1 barrier is likely to proceed via a bimolecular process and with a small barrier. For more information, also see Supporting Information.
  • 59
    • 79851483614 scopus 로고    scopus 로고
    • -1 energy benefits, in better agreement with the experiments. We also note that there are many possible isomeric structures of both 8b and 3b; those in the schemes are the most stable ones
    • -1 energy benefits, in better agreement with the experiments. We also note that there are many possible isomeric structures of both 8b and 3b; those in the schemes are the most stable ones.
  • 60
    • 79851494284 scopus 로고    scopus 로고
    • -1, in better agreement with the experiments
    • -1, in better agreement with the experiments.
  • 61
    • 79851471709 scopus 로고    scopus 로고
    • w3
    • w3.
  • 64
    • 79851479298 scopus 로고    scopus 로고
    • We have applied several different starting geometries as well as initial optimizations with different fixed C2 carbon-hydroxide oxygen distances, and reduced step sizes to locate this minimum
    • We have applied several different starting geometries as well as initial optimizations with different fixed C2 carbon-hydroxide oxygen distances, and reduced step sizes to locate this minimum.
  • 71
    • 17244367197 scopus 로고    scopus 로고
    • z.ast; scaling factor of 0.9679 was suggested
    • z.ast; scaling factor of 0.9679 was suggested: Andersson, M. P.; Uvdal, P. J. Phys. Chem. A 2005, 109, 2937-2941.
    • (2005) J. Phys. Chem. A , vol.109 , pp. 2937-2941
    • Andersson, M.P.1    Uvdal, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.