메뉴 건너뛰기




Volumn 22, Issue 1, 2004, Pages 12-24

Carbon-protonation of the pyrimidine ring: The story of a small molecule NMR problem

Author keywords

Carbon protonation; Identification of an unknown compound; NMR; Pyrimidine; Structural hypotheses; Structure determination

Indexed keywords

CARBON; PYRIMIDINE DERIVATIVE;

EID: 18444413967     PISSN: 15466086     EISSN: 15525023     Source Type: Journal    
DOI: 10.1002/cmr.a.20009     Document Type: Article
Times cited : (6)

References (15)
  • 1
    • 0242417590 scopus 로고    scopus 로고
    • Protonation of the pyrimidine ring at the C(5) position: Formation of a stable cationic σ-complex
    • Demeter Á, Wéber Cs, Brlik J. 2003. Protonation of the pyrimidine ring at the C(5) position: Formation of a stable cationic σ-complex. J Am Chem Soc 125:2535-2540.
    • (2003) J Am Chem Soc , vol.125 , pp. 2535-2540
    • Demeter, Á.1    Wéber, Cs.2    Brlik, J.3
  • 2
    • 37049086083 scopus 로고
    • Structural studies on bioactive compounds. Part 6. Determination of the sites of protonation on three 2,4-diaminopyrimidines of pharmaceutical importance by proton-couple carbon-13 and proton nuclear magnetic resonance spectroscopy
    • Threadgill MD, Griffin RJ, Stevens MFG, Wong SK. 1987. Structural studies on bioactive compounds. Part 6. Determination of the sites of protonation on three 2,4-diaminopyrimidines of pharmaceutical importance by proton-couple carbon-13 and proton nuclear magnetic resonance spectroscopy. J Chem Soc Perkin Trans I 10:2229-2234.
    • (1987) J Chem Soc Perkin Trans I , vol.10 , pp. 2229-2234
    • Threadgill, M.D.1    Griffin, R.J.2    Stevens, M.F.G.3    Wong, S.K.4
  • 3
    • 0018843239 scopus 로고
    • Nitrogen-15 spectroscopy. Part 5. Nitrogen-15 NMR studies of aminopyridines, aminopyrimidines, and of some diazine N-oxides
    • Städeli W, von Philipsborn W, Wick A, Kompiš I. 1980. Nitrogen-15 spectroscopy. Part 5. Nitrogen-15 NMR studies of aminopyridines, aminopyrimidines, and of some diazine N-oxides. Helv Chim Acta 63: 504-522.
    • (1980) Helv Chim Acta , vol.63 , pp. 504-522
    • Städeli, W.1    Von Philipsborn, W.2    Wick, A.3    Kompiš, I.4
  • 4
    • 0001679887 scopus 로고
    • Proton and carbon-13 nuclear magnetic resonance studies of substituted pyrimidines. 2. Monoprotonation of methyl- and aminopyrimidines
    • Riand J, Chenon MT, Lumbroso-Bader N. 1977. Proton and carbon-13 nuclear magnetic resonance studies of substituted pyrimidines. 2. Monoprotonation of methyl- and aminopyrimidines. J Am Chem Soc 99:6838-6845.
    • (1977) J Am Chem Soc , vol.99 , pp. 6838-6845
    • Riand, J.1    Chenon, M.T.2    Lumbroso-Bader, N.3
  • 5
    • 0014705679 scopus 로고
    • Protonation of amino and hydroxypyrimidines. NMR-spectra and structures of mono and dications
    • Wagner R, von Philipsborn W. 1970. Protonation of amino and hydroxypyrimidines. NMR-spectra and structures of mono and dications. Helv Chim Acta 53:299-320.
    • (1970) Helv Chim Acta , vol.53 , pp. 299-320
    • Wagner, R.1    Von Philipsborn, W.2
  • 6
    • 0030930938 scopus 로고    scopus 로고
    • Protonation sites in pyrimidine and pyrimidinamines in the gas phase
    • Nguyen VQ, Tureček F. 1997. Protonation sites in pyrimidine and pyrimidinamines in the gas phase. J Am Chem Soc 119:2280-2290.
    • (1997) J Am Chem Soc , vol.119 , pp. 2280-2290
    • Nguyen, V.Q.1    Tureček, F.2
  • 7
    • 37049092669 scopus 로고
    • Proton and carbon-13 nuclear magnetic resonance studies of substituted pyrimidines. Part 6. Carbon-13-proton coupling constants for some monoprotonated methyl- and aminopyrimidines
    • Riand J, Coupry C, Chenon MT. 1981. Proton and carbon-13 nuclear magnetic resonance studies of substituted pyrimidines. Part 6. Carbon-13-proton coupling constants for some monoprotonated methyl- and aminopyrimidines. J Chem Soc Perkin Trans II 5:783-788.
    • (1981) J Chem Soc Perkin Trans II , vol.5 , pp. 783-788
    • Riand, J.1    Coupry, C.2    Chenon, M.T.3
  • 8
    • 0242613219 scopus 로고
    • An NMR method for the quantitative determination of the N-1:N-3 protonation ratio in 2,4-diaminopyrimidine
    • Griffiths DV, Swetnam SP. 1981. An NMR method for the quantitative determination of the N-1:N-3 protonation ratio in 2,4-diaminopyrimidine. J Chem Soc Chem Commun 1224-1225.
    • (1981) J Chem Soc Chem Commun , pp. 1224-1225
    • Griffiths, D.V.1    Swetnam, S.P.2
  • 9
    • 0013318633 scopus 로고
    • Protonation of N,N′,N″-triphenyl-1,3,5-triaminobenzenes: Stable σ-complexes
    • Glatzhofer DT, Allen D, Taylor RW. 1990. Protonation of N,N′,N″-triphenyl-1,3,5-triaminobenzenes: Stable σ-complexes. J Org Chem 55:6229-6231.
    • (1990) J Org Chem , vol.55 , pp. 6229-6231
    • Glatzhofer, D.T.1    Allen, D.2    Taylor, R.W.3
  • 10
    • 0001773903 scopus 로고
    • 1,3,5-Tris(dialkylamino)benzenes: Model compounds for the electrophilic substitution and oxidation of aromatic compounds
    • Effenberger F. 1989. 1,3,5-Tris(dialkylamino)benzenes: Model compounds for the electrophilic substitution and oxidation of aromatic compounds. Acc Chem Res 22:27-35.
    • (1989) Acc Chem Res , vol.22 , pp. 27-35
    • Effenberger, F.1
  • 11
    • 0013310194 scopus 로고
    • Spectroscopic studies on the protonation of s-triaminobenzene
    • Yamaoka T, Hosoya H, Nagakura S. 1968. Spectroscopic studies on the protonation of s-triaminobenzene. Tetrahedron 24:6203-6213.
    • (1968) Tetrahedron , vol.24 , pp. 6203-6213
    • Yamaoka, T.1    Hosoya, H.2    Nagakura, S.3
  • 12
    • 0242528502 scopus 로고
    • Thermochemical studies on the protonation of 1,3,5-triaminobenzene
    • Yamaoka T, Hosoya H, Nagakura S. 1970. Thermochemical studies on the protonation of 1,3,5-triaminobenzene. Tetrahedron 26:4125-4130.
    • (1970) Tetrahedron , vol.26 , pp. 4125-4130
    • Yamaoka, T.1    Hosoya, H.2    Nagakura, S.3
  • 13
    • 0242444989 scopus 로고
    • Protonation of 1,3,5-triaminobenzenes in aqueous solutions. Thermodynamics and kinetics of the formation of stable σ-complexes
    • Knoche W, Schoeller W, Schomaecker R, Vogel S. 1988. Protonation of 1,3,5-triaminobenzenes in aqueous solutions. Thermodynamics and kinetics of the formation of stable σ-complexes. J Am Chem Soc 110: 7484-7489.
    • (1988) J Am Chem Soc , vol.110 , pp. 7484-7489
    • Knoche, W.1    Schoeller, W.2    Schomaecker, R.3    Vogel, S.4
  • 14
    • 0003125654 scopus 로고
    • Protonation of triaminobenzenes in aqueous solution: Reactions involving aromatic compounds, σ-complexes and cyanine ions
    • Sachs W, Knoche W, Herrmann C. 1991. Protonation of triaminobenzenes in aqueous solution: Reactions involving aromatic compounds, σ-complexes and cyanine ions. J Chem Soc Perkin Trans II 5:701-710.
    • (1991) J Chem Soc Perkin Trans II , vol.5 , pp. 701-710
    • Sachs, W.1    Knoche, W.2    Herrmann, C.3
  • 15
    • 0242613216 scopus 로고
    • Carbon-carbon and carbon-proton NMR couplings
    • Marchand AP, ed. Deerfield Beach, FL: Verlag Chemie International
    • Marshall JL. 1983. Carbon-carbon and carbon-proton NMR couplings. In: Marchand AP, ed. Methods in stereochemical analysis, Vol. 2. Deerfield Beach, FL: Verlag Chemie International, pp. 33-38.
    • (1983) Methods in Stereochemical Analysis , vol.2 , pp. 33-38
    • Marshall, J.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.