2009-52-1Relevant articles and documents
Molecular and crystal structures of dialkylated adenines (N6,N9-Me2Ade, N3,N6-MeBnAde) and cytosines (N1,N4-Me2Cyt)
Krüger, Thomas,Wagner, Christoph,Bruhn, Clemens,Lis, Tadeusz,Steinborn, Dirk
, p. 110 - 114 (2008)
N6,N9-Dimethyladenine (N6,N9-Me2Ade, 1) and N1,N4-dimethylcytosine (N1,N4-Me2Cyt, 3) were obtained by conventional methods, whereas the reaction of N6-benzyladenine with MeI/NaOH resulted in the formation of N3,N6-MeBnAde (2a) and N6,N9-BnMeAde (2b). All compounds were fully characterized by microanalysis, NMR spectroscopy (1H, 13C) and 1, 2a·2MeOH and 3 also by single-crystal X-ray diffraction analyses. In single-crystals of 1, obtained from THF solutions, twofold N6-H···N7′ hydrogen-bonded dimeric units (N6,N9-Me2Ade)2 (AA12 type according to Jeffrey and Saenger, 1991) were found. This proved to be another modification than that obtained by crystallization N6,N9-Me2Ade from MeOH/PhCl (Sternglanz, 1978). Crystals of 2a·2MeOH exhibited an analogous hydrogen bond pattern as found in 1. The shorter N6···N7′ distance in 2a·2MeOH (2.932(2) A?) indicates slightly stronger hydrogen bonds than in 1 (3.078(3) A?). Crystals of 3 are built up from centrosymmetric dimers (N1,N4-Me2Cyt)2 having a twofold N4-H···N3′ hydrogen bond, thus exhibiting the CC32 hydrogen bond pattern. The hydrogen bonding patterns in the dialkylated nucleobase derivatives are discussed in terms of those found in crystals of the less substituted nucleobases N9-MeAde and Cyt/N1-MeCyt, respectively.
Unusual reactivity of purinophanes due to stereoelectronic effect
Sakata,Higuchi,Doyama,Higashii,Mitsuoka,Misumi
, p. 3155 - 3160 (1989)
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Synthesis and Properties of Purinophanes: Relationship between the Magnitude of Hypochromism and Stacking Geometry of Purine Rings
Seyama, F.,Akahori, K.,Sakata, Y.,Misumi, S.,Aida, M.,Nagata, C.
, p. 2192 - 2201 (2007/10/02)
Twelve purinophanes 1-12, in which two purine rings are fixed with different modes of stacking by two or three polymethylene chains, have been prepared by either stepwise introduction of the linking chains or quasi-dimerization of disubstituted purine der