Crystal-stabilisation of an elusive 4,6-pyrimidinedione dimer

被引：4
作者：
Katrusiak, Anna
Katrusiak, Andrzej
机构：
[1] Karol Marcinkowski Univ Med Sci, Dept Organ Chem, PL-60780 Poznan, Poland
[2] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 11期
关键词：
D O I：
10.1016/j.tetlet.2007.01.096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The formation of a disproportionation dimer of 4,6-pyrimidinedione 1, 2-(4,6-dioxo-5-pyrimidinyl)-4,6-dioxo-1,2,3,5,5pentahydropyrimidine 2, results from the reactivity of the inner-salt tautomers or ions of 1, contrasting to the general properties of nucleobases which are all stable in the lactam or dilactam molecular forms. The observation of dimer 2, indefinitely stable in the crystalline state, reveals an unusual chemical reactivity strongly dependent on the H-tautomeric forms of the substrate and product. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：1935 / 1938
页数：4
相关论文
共 25 条
[11]   COVALENTLY LINKED PURINE PYRIMIDINE ANALOGS - STRUCTURE OF 7-(4,6-DIOXO-5-PYRIMIDINYL)-THEOPHYLLINE DIHYDRATE, C11H10N6O4.2H2O [J].
GAVUZZO, E ;
MAZZA, F ;
TAMBURRINI, A ;
CASINI, G ;
CAROTTI, A .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1984, 40 (MAY) :856-858
[12]   DNA MODELS - MUTATIONS CAUGHT IN THE ACT [J].
GOODMAN, MF .
NATURE, 1995, 378 (6554) :237-238
[13]  
Hassall KA, 1990, BIOCH USES PESTICIDE, DOI [10.1007/978-1-349-20990-3, DOI 10.1007/978-1-349-20990-3]
[14]   AIDS-DRIVEN NUCLEOSIDE CHEMISTRY [J].
HURYN, DM ;
OKABE, M .
CHEMICAL REVIEWS, 1992, 92 (08) :1745-1768
[15]   POTENTIALLY TAUTOMERIC AZINES .4. FINE STRUCTURE OF 4,6-DIHYDROXYPYRIMIDINES [J].
KATRITZK.AR ;
POPP, FD ;
WARING, AJ .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (06) :565-&
[16]   Ionic disparity of identical molecules in polymorphs [J].
Katrusiak, A ;
Katrusiak, A .
ORGANIC LETTERS, 2003, 5 (11) :1903-1905
[17]   PROTON MAGNETIC RESONANCE SPECTRA AND STRUCTURE OF 4,6-DIHYDROXY-PYRIMIDINE AND ITS DERIVATIVES [J].
KHEIFETS, GM ;
KHROMOVB.NV ;
KOLTSOV, AI ;
VOLKENST.MV .
TETRAHEDRON, 1967, 23 (03) :1197-&
[18]  
PERIGAUD C, 1992, NUCLEOS NUCLEOT, V11, P902
[19]   Effect of proton transfer on the anionic and cationic pathways of pyrimidine photodimer cleavage.: A computational study [J].
Rak, J ;
Voityuk, AA ;
Michel-Beyerle, ME ;
Rösch, N .
JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (18) :3569-3574
[20]  
Ruzsicska B. P., 1995, CRC HDB ORGANIC PHOT, P1289
123