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Volumn 75, Issue 24, 2010, Pages 8400-8409

Theoretical study of 1,6-anhydrosugar formation from phenyl d-glucosides under basic condition: Reasons for higher reactivity of β-anomer

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; ANOMERIC CARBON; ANOMERICS; BASIC CONDITIONS; COMPUTATIONAL RESULTS; EXPERIMENTAL OBSERVATION; LEVOGLUCOSAN; METHYLENE GROUPS; OH GROUP; OXYANIONS; STEREOELECTRONIC EFFECT; THEORETICAL STUDY; TRANSITION STATE;

EID: 78650376444     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101494g     Document Type: Article
Times cited : (9)

References (61)
  • 1
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    • Nevell, T. P., Zeronian, S. H., Eds.; Ellis Horwood, Chichester, UK
    • Nevell, T. P. In Cellulose Chemistry and its Applications; Nevell, T. P., Zeronian, S. H., Eds.; Ellis Horwood, Chichester, UK, 1985; p 223.
    • (1985) Cellulose Chemistry and Its Applications , pp. 223
    • Nevell, T.P.1
  • 38
    • 78650382109 scopus 로고    scopus 로고
    • Gaussian 03, Revision C.02; Gaussian, Inc., Wallingford, CT,. See the Supporting Information for the complete reference
    • Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc., Wallingford, CT, 2004. See the Supporting Information for the complete reference.
    • (2004)
    • Pople, J.A.1
  • 39
    • 78650403249 scopus 로고    scopus 로고
    • Gaussian 09, Revision A.02; Gaussian, Inc., Wallingford, CT,. See the Supporting Information for the complete reference
    • Pople, J. A. Gaussian 09, Revision A.02; Gaussian, Inc., Wallingford, CT, 2009. See the Supporting Information for the complete reference.
    • (2009)
    • Pople, J.A.1
  • 42
    • 78650351064 scopus 로고    scopus 로고
    • 4 conformer in both α- and β-anomers; see refs 1d, 4b, and 5
    • 4 conformer in both α- and β-anomers; see refs 1d, 4b, and 5.
  • 43
    • 78650384949 scopus 로고    scopus 로고
    • 1 conformations, the present result does not rule out the possibility that the C6-oxyanion exists to a minor extent in the equilibrium with other conformations
    • 1 conformations, the present result does not rule out the possibility that the C6-oxyanion exists to a minor extent in the equilibrium with other conformations.
  • 44
    • 78650360348 scopus 로고    scopus 로고
    • 1
    • 1.
  • 49
    • 78650402735 scopus 로고    scopus 로고
    • α
    • α.
  • 50
    • 78650337681 scopus 로고    scopus 로고
    • LG, indicating that the C4-oxyanion is not an equilibrium species
    • LG, indicating that the C4-oxyanion is not an equilibrium species.
  • 51
    • 78650336012 scopus 로고    scopus 로고
    • Iβ.
  • 52
    • 78650316856 scopus 로고    scopus 로고
    • 0‡ value is only approximately estimated in solution
    • 0‡ value is only approximately estimated in solution.
  • 55
    • 78650353127 scopus 로고    scopus 로고
    • 1β. This is because not only the CT from the O5 but those from the nucleophilic oxygen and the leaving group also affect the charge of the C1
    • 1β. This is because not only the CT from the O5 but those from the nucleophilic oxygen and the leaving group also affect the charge of the C1.
  • 56
    • 78650319245 scopus 로고    scopus 로고
    • The HOMO- n represents the n th MO counting from the HOMO toward the low-energy direction
    • The HOMO- n represents the n th MO counting from the HOMO toward the low-energy direction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.