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37049167549
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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Brown, D.J.1
Short, L.N.2
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19
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37049145242
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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J. Chem. Soc.
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Brown, D.J.1
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Mason, S.F.3
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20
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37049044961
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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Albert, A.1
Spinner, E.2
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21
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0345059549
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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J. Org. Chem.
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Inoue, Y.1
Furutachi, N.2
Nakanishi, K.3
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22
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0346271873
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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J. Mol. Struct.
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Nowak, M.J.1
Szczepaniak, K.2
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23
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0002580375
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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Spectrochimica Acta
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Lapinski, L.1
Fulara, J.2
Nowak, M.J.3
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24
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0005966492
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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J. Am. Chem. Soc.
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Stimson, M.M.1
O'Donnell, M.J.2
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25
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0013845744
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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Acta Crystallogr.
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, pp. 797
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Sharma, B.D.1
McConnell, J.F.2
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26
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For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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2742537085
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note
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Preliminary theoretical calculations in the gas phase, performed at semiempirical (MNDO and PM3) level, predict consistently for compounds 1, 2 and 3, the enol tautomer to be of highest stability, while among the keto tautomers, the N3 form is calculated as more stable vs. the N1 form by ca. 10 kcal/mol. However, it is known that semiempirical methods are not suited for studies of the relative stability of tautomers and more advanced ab initio quantum mechanical calculations are desired for accurate predictions.
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33
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0003520774
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Silverstein, R.M.1
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0004200219
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University Science Books, Mill Valley, California
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T. N. Sorrell, Interpreting Spectra of Organic Molecules, University Science Books, Mill Valley, California, 1988, pp. 25.
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Sorrell, T.N.1
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Academic Press, New York
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F. A. Bovey, L. Jelinski and P. A. Mirav, Nuclear Magnetic Resonance Spectroscopy, 2nd ed., Academic Press, New York, 1988.
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42
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2742544797
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note
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3 irradiation of the 6-methyl is meaningless in terms of the NOE effect on the NH, due to concomitant saturation transfer to the water peak.
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49
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0014708841
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For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
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For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
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For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
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33845281874
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For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
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For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
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