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Volumn 126, Issue 13, 2004, Pages 4366-4374

Formation and Stability of N-Heterocyclic Carbenes in Water: The Carbon Acid pKa of Imidazolium Cations in Aqueous Solution

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM; GIBBS FREE ENERGY; POSITIVE IONS; RATE CONSTANTS; THERMODYNAMIC STABILITY;

EID: 1842502863     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039890j     Document Type: Article
Times cited : (476)

References (77)
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    • (2002) Carbene Chemistry , pp. 153-176
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    • Brinker, U. H., Ed.; JAI Press Inc.: Stamford, CT
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    • (1998) Advances in Carbene Chemistry , vol.2 , pp. 245-295
    • Warkentin, J.1
  • 20
    • 1842461612 scopus 로고    scopus 로고
    • note
    • -1.
  • 26
    • 1842461615 scopus 로고    scopus 로고
    • note
    • a = 12.3 kcal/mol) at 30 °C (l = 2.0).
  • 34
    • 0002347758 scopus 로고
    • Rappoport, Z., Ed.; John Wiley and Sons: Chichester
    • Keeffe, J. R.; Kresge, A. J. In The Chemistry of Enols; Rappoport, Z., Ed.; John Wiley and Sons: Chichester, 1990; pp 399-480.
    • (1990) The Chemistry of Enols , pp. 399-480
    • Keeffe, J.R.1    Kresge, A.J.2
  • 47
    • 1842513786 scopus 로고    scopus 로고
    • note
    • -d).
  • 51
    • 1842618338 scopus 로고    scopus 로고
    • note
    • a = 15.74.
  • 52
    • 0001965020 scopus 로고    scopus 로고
    • Brinker, U. H., Ed.; JAI Press Inc.: Stamford, CT
    • Bonneau, R.; Liu, M. T. H. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press Inc.: Stamford, CT, 1998; Vol. 2, pp 1-28.
    • (1998) Advances in Carbene Chemistry , vol.2 , pp. 1-28
    • Bonneau, R.1    Liu, M.T.H.2
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    • 0002357673 scopus 로고
    • Brinker, U. H., Ed.; JAI Press Inc.: Stamford, CT
    • Moss, R. A. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press Inc.: Stamford, CT, 1994; Vol. 1, pp 59-88.
    • (1994) Advances in Carbene Chemistry , vol.1 , pp. 59-88
    • Moss, R.A.1
  • 55
    • 1842513785 scopus 로고    scopus 로고
    • note
    • To the best of our knowledge, the only other thermodynamic data for such a process is δH = -42.1 kcal/mol for the 1,2-H shift at methylchlorocarbene to give vinyl chloride in heptane at 295 K, determined using photoacoustic calorimetry.
  • 65
    • 1842618334 scopus 로고    scopus 로고
    • note
    • a = 2.68 for the thiazolium cation in water at 25 °C.
  • 71
    • 1842566201 scopus 로고    scopus 로고
    • note
    • o = +14.4 kcal/mol has been computed at the B3LYP/6-31G(d)//B3LYP/6-31G(d) level.
  • 73
    • 1842618336 scopus 로고    scopus 로고
    • note
    • Calculated as the difference in the energy changes for the 1,2-H shift at the two carbenes computed at the MP4/6-311G(d,p)//MP2/6-31IG(d,p)//MP2/6-31G(d) level.
  • 74
    • 1842618337 scopus 로고    scopus 로고
    • note
    • At the B3LYP/6-31G* level the 1,3-dimethylimidazol-2-yl carbene and the corresponding saturated 1,3-dimethylimidazolin-2-yl carbene are computed to have identical proton affinities of 266.0 kcal/mol.
  • 77
    • 1842566200 scopus 로고    scopus 로고
    • note
    • a = 8.5 kcal/mol).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.