Determination of the group electronegativity of CF3 group in 3'-O- CF3-thymidine by 1H-NMR

Nucleosides and Nucleotides

Volumn 18, Issue 4-5, 1999, Pages 1035-1053

  Thibaudeau, C ^a   Nishizono, N ^b   Sumita, Y ^b   Matsuda, A ^b   Chattopadhyaya, J ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROCARBON; NUCLEOSIDE; THYMIDINE DERIVATIVE;

ANALYTIC METHOD; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; CONFORMATION; ELECTRICITY; ENTHALPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0033059372     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257779908041642     Document Type: Conference Paper

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60. 3), as evidenced by their rather small standard deviations (Table 2).
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62. The amino group of 3′-amino-2′,3′-dideoxythymidine should be protonated about 50% or more in ca pH 7.0 solution considering the pKa of 3′-amino is the very similar to that of 2′-amino group in the respective nucleosides: the pKa value of the amino group in 2′-amino-2′-deoxyuridine was reported to be 6.2, see (a) Aurup, H.; Tuschl, T.; Benseler, F.; Ludwig, J.; Eckstein, F. Nucleic Acids Res., 1994, 22, 20, and (b) Verheyden, J. P. H.; Wagner, D.; Moffatt, J. G. J. Org. Chem. 1971, 36, 250.
63. The amino group of 3′-amino-2′,3′-dideoxythymidine should be protonated about 50% or more in ca pH 7.0 solution considering the pKa of 3′-amino is the very similar to that of 2′-amino group in the respective nucleosides: the pKa value of the amino group in 2′-amino-2′-deoxyuridine was reported to be 6.2, see (a) Aurup, H.; Tuschl, T.; Benseler, F.; Ludwig, J.; Eckstein, F. Nucleic Acids Res., 1994, 22, 20, and (b) Verheyden, J. P. H.; Wagner, D.; Moffatt, J. G. J. Org. Chem. 1971, 36, 250.