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Volumn 118, Issue 43, 1996, Pages 10494-10504

Transition state imbalances in gas phase proton transfers. Ab initio study of the carbon-to-carbon proton transfer from the protonated acetaldehyde cation to acetaldehyde enol

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE;

EID: 0029848535     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960233j     Document Type: Article
Times cited : (34)

References (67)
  • 2
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    • note
    • 3,4
  • 6
    • 10544236404 scopus 로고    scopus 로고
    • note
    • 0 = 0). In proton transfers statistical factors are sometimes included.
  • 10
    • 10544230076 scopus 로고    scopus 로고
    • note
    • Y, does not necessarily apply, in which case n may be >2 or <2.
  • 13
    • 10544232481 scopus 로고    scopus 로고
    • note
    • 3
  • 14
    • 10544234499 scopus 로고    scopus 로고
    • note
    • 2=CHOH system they differ by less than 0.1 kcal/mol.
  • 15
    • 10544254127 scopus 로고    scopus 로고
    • note
    • 13
  • 16
    • 10544238372 scopus 로고    scopus 로고
    • See the paragraph concerning supporting information at the end of this paper
    • See the paragraph concerning supporting information at the end of this paper.
  • 19
    • 10544234064 scopus 로고    scopus 로고
    • note
    • Enthalpies determined at the MP2/6-311+G**//MP2/6-311+G** level.
  • 23
    • 0003102329 scopus 로고
    • Bauers, M. T., Ed.; Academic Press: San Francisco
    • Aue, D. H.; Bowers, M. T. In Gas Phase Ion Chemistry; Bauers, M. T., Ed.; Academic Press: San Francisco, 1979; Vol. 2, p 1.
    • (1979) Gas Phase Ion Chemistry , vol.2 , pp. 1
    • Aue, D.H.1    Bowers, M.T.2
  • 26
    • 10544243239 scopus 로고    scopus 로고
    • For a discussion of the uncertainties in the proton affinities, see ref 23
    • For a discussion of the uncertainties in the proton affinities, see ref 23.
  • 31
    • 10544228822 scopus 로고    scopus 로고
    • note
    • 13 show a strong dependence on the computational level and particularly on the method (Mulliken vs NPA) but there is little variation in the group charges (Table 2).
  • 32
    • 10544232173 scopus 로고    scopus 로고
    • 2Y
    • 2Y.
  • 33
    • 10544238978 scopus 로고    scopus 로고
    • note
    • 31
  • 40
    • 10544231755 scopus 로고    scopus 로고
    • note
    • B when the remote substituent is closer to the Y group than to the α carbon, e.g., formula presented For a detailed discussion of these examples, see ref 4.
  • 41
    • 10544252143 scopus 로고    scopus 로고
    • note
    • res the change in the equilibrium constant caused by the change in resonance stabilization of the carbanions. Both forms of the equation are of course equivalent.
  • 42
    • 10544256855 scopus 로고    scopus 로고
    • note
    • ‡ is enhanced.
  • 43
    • 10544247675 scopus 로고    scopus 로고
    • For more details, see ref 4
    • For more details, see ref 4.
  • 44
    • 10544227628 scopus 로고    scopus 로고
    • See in particular eq 5 of ref 1
    • See in particular eq 5 of ref 1.
  • 49
    • 10544230927 scopus 로고    scopus 로고
    • 9b report that polarizability effects may be important in some cases
    • 9b report that polarizability effects may be important in some cases.
  • 50
    • 0000549339 scopus 로고
    • (a) Cybulski, S. M.; Scheiner, S. J. Am. Chem. Soc. 1987, 109, 4199. See also: Scheiner, S.; Wang, L. J. Am. Chem. Soc. 1992, 114, 3650.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 4199
    • Cybulski, S.M.1    Scheiner, S.2
  • 51
    • 0000824861 scopus 로고
    • (a) Cybulski, S. M.; Scheiner, S. J. Am. Chem. Soc. 1987, 109, 4199. See also: Scheiner, S.; Wang, L. J. Am. Chem. Soc. 1992, 114, 3650.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 3650
    • Scheiner, S.1    Wang, L.2
  • 55
    • 10544231332 scopus 로고    scopus 로고
    • note
    • It is reasonable to expect that the entropy terms of the various reactions are very similar or identical and hence eq 10 is equally valid for enthalpies.
  • 56
    • 10544245959 scopus 로고    scopus 로고
    • note
    • 2 groups are smaller in the transition state of eq 4 compared to that of eq 1.
  • 57
    • 10544250136 scopus 로고    scopus 로고
    • note
    • 1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.