2011
DOI: 10.1021/cg200539a
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Design of a Series of Isostructural Co-Crystals with Aminopyrimidines: Isostructurality through Chloro/Methyl Exchange and Studies on Supramolecular Architectures

Abstract: A series of 17 co-crystals involving 2-amino-4-chloro-6-methyl pyrimidine/2-amino-4,6-dimethyl pyrimidine with various carboxylic acids, C7H5O2-R (where R = H, Cl, CH3, NO2, OCH3, COOH) and C9H8O2, have been prepared in which the analogues differ only with respect to chlorine and methyl groups. The basis of this work is the formation of isostructural co-crystals based on the chloro/methyl interchange. The results show good success in the harvest of isostructural compounds. Isostructurality calculations have be… Show more

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Cited by 55 publications
(36 citation statements)
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“…They have the geometry of trigonal bipyramidal with three C atoms from phenyl groups forming the equatorial plane and two O atoms from carboxylate groups occupying the axial sites. The axial angles of OeSneO are 175.6(3) and 175.8 (2) respectively and relevant SneO bond lengths are in the range of 2.166(7)e2.404(7)Å. These data are comparable with those found in {[Ph 3 SnO 2 P(OC 2 H 5 ) 2 ] 2 } n [33].…”
Section: Crystal Structures Of [(Ph 3 Sn) 8 (Btec) 2 (Ch 2 Ch 3 Oh) 2supporting
confidence: 80%
“…They have the geometry of trigonal bipyramidal with three C atoms from phenyl groups forming the equatorial plane and two O atoms from carboxylate groups occupying the axial sites. The axial angles of OeSneO are 175.6(3) and 175.8 (2) respectively and relevant SneO bond lengths are in the range of 2.166(7)e2.404(7)Å. These data are comparable with those found in {[Ph 3 SnO 2 P(OC 2 H 5 ) 2 ] 2 } n [33].…”
Section: Crystal Structures Of [(Ph 3 Sn) 8 (Btec) 2 (Ch 2 Ch 3 Oh) 2supporting
confidence: 80%
“…The infrared absorption spectroscopy is a promishing tool to investigate the nature and formation of organic salt or cocrystal by identifying the existence of proton transfer or strong intermolecular hydrogen bond interactions which are taking place between the molecules and the associated environment [18e20]. A series of seventeen crystals of pyrimidine derivatives with various carboxylic acids have been reported earlier [21]. Experimental vibrational spectroscopy studies of many cocrystals and salts [22e26] and quantum chemical calculations of pharmaceutical cocrystals have been reported [27e29].…”
Section: Introductionmentioning
confidence: 99%
“…In the Crick-Watson model of DNA, the bases in the adeninethymine base pair are linked by one N-HÁ Á ÁN hydrogen bond and one N-HÁ Á ÁO hydrogen bond, while in the cytosineguanine pair, the bases are linked by one N-HÁ Á ÁN and two N-HÁ Á ÁO hydrogen bonds. Accordingly, there has been much ISSN 2053ISSN -2296 # 2017 International Union of Crystallography interest recently in the hydrogen-bonding properties of aminopyrimidines (Ebenezer et al, 2011;Tamilselvi & Muthiah, 2011;Ebenezer & Muthiah, 2012;Karthikeyan et al, 2015), prompted in part by the consideration that targeted drug action of pharmaceuticals containing this functionality is likely to depend heavily on molecular recognition processes involving hydrogen bonding. As part of a broader general study of hydrogen bonding in aminopyrimidine derivatives, we have now investigated the 1:1 salt formed between 4-amino-5chloro-2,6-dimethylpyrimidine and 5-chloro-2-hydroxybenzoic acid, which crystallizes as two tautomeric products, namely 6-amino-5-chloro-2,4-dimethylpyrimidin-1-ium 5-chloro-2hydroxybenzoate, (I), and 4-amino-5-chloro-2,6-dimethylpyrimidin-1-ium 5-chloro-2-hydroxybenzoate, (II), whose structures we report here (Figs.…”
Section: Introductionmentioning
confidence: 99%