{"title":"Supramolecular Cocrystal of 2-Amino-4-Chloro-6- Methylpyrimidine with 4-Methylbenzoic Acid: Synthesis, Structural Determinations and Quantum Chemical Investigations","authors":"Nuridayanti Che Khalib, Kaliyaperumal Thanigaimani, Suhana Arshad, Ibrahim Abdul Razak","volume":108,"journal":"International Journal of Chemical and Molecular Engineering","pagesStart":1350,"pagesEnd":1360,"ISSN":"1307-6892","URL":"https:\/\/publications.waset.org\/pdf\/10003014","abstract":"
The 1:1 cocrystal of 2-amino-4-chloro-6-
\r\nmethylpyrimidine (2A4C6MP) with 4-methylbenzoic acid (4MBA)
\r\n(I) has been prepared by slow evaporation method in methanol,
\r\nwhich was crystallized in monoclinic C2\/c space group, Z = 8, and a
\r\n= 28.431 (2) Å, b = 7.3098 (5) Å, c = 14.2622 (10) Å and β =
\r\n109.618 (3)°. The presence of unionized –COOH functional group in
\r\ncocrystal I was identified both by spectral methods (1H and 13C
\r\nNMR, FTIR) and X-ray diffraction structural analysis. The
\r\n2A4C6MP molecule interact with the carboxylic group of the
\r\nrespective 4MBA molecule through N—H\u22efO and O—H\u22efN
\r\nhydrogen bonds, forming a cyclic hydrogen–bonded motif R2
\r\n2(8).
\r\nThe crystal structure was stabilized by Npyrimidine—H\u22efO=C and
\r\nC=O—H\u22efNpyrimidine types hydrogen bonding interactions.
\r\nTheoretical investigations have been computed by HF and density
\r\nfunction (B3LYP) method with 6–311+G (d,p)basis set. The
\r\nvibrational frequencies together with 1H and 13C NMR chemical
\r\nshifts have been calculated on the fully optimized geometry of
\r\ncocrystal I. Theoretical calculations are in good agreement with the
\r\nexperimental results. Solvent–free formation of this cocrystal I is
\r\nconfirmed by powder X-ray diffraction analysis.<\/p>\r\n","references":"[1] C. Janiak, \u201cA critical account on \u03c0-\u03c0 stacking in metal complexes with\r\naromatic nitrogen-containing ligands,\u201d J. Chem. Soc. Dalton. Trans.,\r\npp.3885\u20133896, 2000.\r\n[2] G. R. Desiraju, \u201cC\u2013HO and other weak hydrogen bond. From crystal\r\nengineering to virtual screenin,\u201d Chem. Commun., vol. 24, pp.2995\u2013\r\n3001, 2005.\r\n[3] \u00d6. Almarsson, M. J. Zaworotko, \u201cCrystal engineering of the\r\ncomposition of pharmaceutical phases. Do pharmaceutical cocrystal\r\nrepresent a new path to improved medicines?,\u201d Chem. Commun.,\r\npp.1889\u20131896, 2004.\r\n[4] S. L. Childs, L. J. Chyall, J. T. Dunlap, V. N. Smolenskaya, B. C.\r\nStahly, B. C. Stahly. \u201cCrystal engnineering approach to forming\r\ncocrystals of amine hydrochloric with organic acids. Molecular\r\ncomplexes of fluoxetine hydrochloride with benzoic, succinic and\r\nfumaric acid,\u201d J. Am. 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