Screening, manufacturing, photoluminescence, and molecular recognition of co-crystals: cytosine with dicarboxylic acids

Crystal Growth and Design

Volumn 10, Issue 3, 2010, Pages 1435-1442

  Lee, Tu ^a   Wang, Pu Yun ^a  

^a NATIONAL CENTRAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77949417925     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg901481q     Document Type: Article

References (107)

1. Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. Review: Pharmaceutical Co-Crystals. J. Pharm. Sci. 2006 95, 499-516.
2. Blagden, N. Crystal Engineering of Active Pharmaceutical Ingredients to Improve Solubility and Dissolution Rates. Adv. Drug Delivery Rev. 2007 59, 617-630.
3. Shiraki, K.; Takata, N.; Takano, R.; Hayashi, Y.; Terada, K. Dissolution Improvement and the Mechanism of the Improvement from Cocrystallization of Poorly Water-Soluble Compounds. Pharm. Res. 2008 25, 2581-2592.
4. Jayasankar, A.; Sreenivas Reddy, L.; Bethune, S. J.; Rodrí guezHornedo, N. Role of Cocrystal and Solution Chemistry on the Formation and Stability of Cocrystals with Different Stoichiometry. Cryst. Growth Des. 2009 9, 889-897.
5. Hickey, M. B.; Peterson, M. L.; Scoppettuolo, L. A.; Morrisette, S. L.; Vetter, A.; Guzmán, Remenar, J. F.; Zhang, Z.; Tawa, M. D.; Haley, S.; Zaworotko, M. J.; Almarsson, Ö. Performance Comparison of a Co-crystal of Carbamazepine with Marketed Product. Eur. J. Pharm. Biopharm. 2007 67, 112-119.
6. Friščić, T.; Jones, W. Cocrystal Architecture and Properties: Design and Building of Chiral and Racemic Structures by SolidSolid Reactions. Faraday Discuss. 2007,136, 167-178.
7. Sokolov, A. N.; Friščić, T.; MacGillivray, L. R. Enforced Faceto-Face Stacking of Organic Semiconductor Building Blocks within Hydrogen-Bonded Molecular Cocrystals. J. Am. Chem. Soc. 2006,128, 2806-2807.
8. Koshima, H.; Miyauchi, M. Polymorphs of a Cocrystal with Achiral and Chiral Structures Prepared by Pseudoseeding: Tryptamine/Hydrocinnamic Acid. Cryst. Growth Des. 2001 1, 355-357.
9. Kawasaki, T.; Jo, K.; Igarashi, H.; Sato, I.; Nagano, M.; Koshima, H.; Soai, K. Asymmetric Amplification Using Chiral Cocrystals Formed from Achiral Organic Molecules by Asymmetric Autocatalysis. Angew. Chem. 2005 117, 2834-2837.
10. Horikoshi, R.; Nambu, C.; Mochida, T. Supramolecular Assembly of Ferrocenes via Hydrogen Bonds: Dimensional Variation in Ferrocenylpyrimidine Complexes with Carboxylic Acids and Aromatic Alcohols. New J. Chem. 2004 28, 26-33.
11. Hollingsworth, M. D. Crystal Engineering: From Structure to Function. Science 2002 295, 2410-2413.
12. Cho, W.; Lee, H. J.; Oh, M. Growth-Controlled Formation of Porous Coordination Polymer Particles. J. Am. Chem. Soc. 2008 130, 16943-16946.
13. Travis Holman, K.; Ward, M. D. Metric Engineering of Crystalline Inclusion Compounds by Structural Mimicry. Angew. Chem., Int. Ed. 2000 39,1653-1656.
14. Lee, T.; Aksay, I. A. Hierarchical Structure-Ferroelectricity Relationships of Barium Titanate Particles. Cryst. Growth Des. 2001,1, 401-419.
15. Zaworotko, M. J. Molecules to Crystals, Crystals to Molecules... and Back Again? Cryst. Growth Des. 2007 7, 4-9.
16. Klussmann, M.; Izumi, T.; White, A. J. P.; Armstrong, A.; Blackmond, D. G. Emergence of Solution-Phase Homochirality via Crystal Engineering of Amino Acids. J. Am. Chem. Soc. 2007 129, 7657-7660.
17. Ahn, S.; Matzger, A. J. Anatomy of one-Dimensional Cocrystals: Randomness into Order. J. Am. Chem. Soc. 2009 131, 13826-13832.
18. Lara-Ochoa, F.; Espinosa-Pérez, G. Crystals and Patents. Cryst. Growth Des. 2007 7, 1213-1215.
19. Bhogala, B. R.; Basavoju, S.; Nangia, A. Tape and Layer Structures in Cocrystals of Some Di- and Tricarboxylic Acids with 4,4′bipyridines and Isonicotinamide. From Binary to Ternary Cocrystals. CrystEngComm 2005 7, 551-562.
20. Clawson, J. S.; Vogt, F. G.; Brum, J.; Sisko, J.; Patience, D. B.; Dai, W.; Sharpe, S.; Jones, A. D.; Pham, T. N.; Johnson, M. N.; Copley, R. C. P. Formation and Characterization of Crystals Containing a Pleuromutilin Derivative, Succinic Acid and Water. Cryst. Growth Des. 2008 8, 4120-4131.
21. Porter, W. W., III; Elie, S. C.; Matzger, A. J. Polymorphism in Carbamazepine Cocrystals. Cryst. Growth Des. 2008 8,14-16.
22. Trask, A. V.; Shan, N.; Samuel Motherwell, W. D.; Jones, W.; Feng, S.; Tan, R. B. H.; Carpenter, J. Selective Polymorph Transformation via Solvent-Drop Grinding. Chem. Commun. 2005, 880-882.
23. Vishweshwar, P.; McMahon, J. A.; Peterson, M. L.; Hickey, M. B.; Shattock, T. R.; Zaworotko, M. J. Crystal Engineering of Pharmaceutical Co-crystals from Polymorphic Active Pharmaceutical Ingredients. Chem. Commun. 2005, 4601-4603.
24. Childs, S. L.; Rodríguez-Hornedo, N.; Screenivas Reddy, L.; Jayasankar, A.; Maheshwari, C.; McCausland, L.; Shipplett, R.; Stahly, B. C. Screening Strategies Based on Solubility and Solution Composition Generate Pharmaceutically Acceptable Cocrystals of Carbamazepine. CrystEngComm 2008,10, 856-864.
25. ter Horst, J. H.; Deij, M. A.; Cains, P. W. Discovering New CoCrystals. Cryst. Growth Des. 2009 9, 1531-1537.
26. Zhang, G. G. Z.; Henry, R. F.; Borchardt, T. B.; Lou, X. Efficient Co-crystal Screening Using Solution-Mediated Phase Transformation. J. Pharm. Sci. 2007 96, 990-995.
27. Trask, A. V.; Samuel Motherwell, W. D.; Jones, W. Solvent-Drop Grinding: Green Polymorph Control of Co-crystallization. Chem. Commun. 2004, 890-891.
28. Weyna, D. R.; Shattock, T.; Vishweshwar, P.; Zaworotko, M. J. Synthesis and Structural Characterization of Cocrystals and Pharmaceutical Cocrystals: Mechanochemistry vs Slow Evaporation. Crys. Growth Des. 2009 9, 1106-1123.
29. Gagniere, E.; Mangin, D.; Puel, F.; Bebon, C.; Klein, J.-P.; Monnier, O.; Garcia, E. Cocrystal Formation in Solution: In Situ Solute Concentration Monitoring of the Two Components and Kinetic Pathways. Cryst. Growth Des. 2009 9, 3376-3383.
30. Bettinetti, G.; Caira, M. R.; Callegari, A.; Merli, M.; Sorrenti, M.; Tadini, C. Structure and Solid-State Chemistry of Anhydrous and Hydrated Crystal Forms of the Trimethoprim-Sulfamethoxypyridazine 1:1 Molecular Complex. J. Pharm. Sci. 2000 89, 478-489.
31. Friščić, T.; Childs, S. L.; Rizvi, S. A. A.; Jones, W. The Role of Solvent in Mechanochemical and Sonochemical Cocrystal Formation: A Solubility-Based Approach for Predicting Cocrystallization Outcome. CrystEngComm 2009,11,418-426.
32. Berry, D. J.; Seaton, C. C.; Clegg, W.; Harrington, R. W.; Coles, S. J.; Horton, P. N.; Hursthouse, M. B.; Storey, R.; Jones, W.; Frišč ić, T.; Blagden, N. Applying Hot-Stage Microscopy to Co-crystal Screening: A Study of Nicotinamide with Seven Active Pharmaceutical Ingredients. Cryst. Growth Des. 2008 8, 1697-1712.
33. Lu, E.; Rodríguez-Hornedo, N.; Suryanarayanan, R. A Rapid Thermal Method for Cocrystal Screening. CrystEngComm 2008 10, 665-668.
34. Seefeldt, K.; Miller, J.; Alvarez-Núñez, F.; Rodríguez-Hornedo, N. Crystallization Pathwyas and Kinetics of CarbamazepineNicotinamide Cocrystals from the Amorphous State by In Situ Thermomicroscopy, Spectroscopy and Calorimetry Studies. J. Pharm. Sci. 2007 96, 1147-1158.
35. Brittain, H. G. Vibrational Spectroscopic Studies of Cocrystals and Salts. 1. The Benzamide-Benzoic Acid System. Cryst. Growth Des. 2009 9, 2492-2499.
36. Vogt, F. G.; Clawson, J. S.; Strohmeier, M.; Edwards, A. J.; Pham, T. N.; Watson, S. A. Solid-State NMR Analysis of Organic Cocrystals and Complexes. Cryst. Growth Des. 2009 9, 921-937.
37. Takata, N.; Shiraki, K.; Takano, R.; Hayashi, Y.; Terada, K. Cocrystal Screening of Stanolone and Mestanolone Using Slurry Crystallization. Cryst. Growth Des. 2008 8, 3032-3037.
38. Wenger, M.; Bernstein, J. An Alternative Crystal Form of Gabapentin: A Cocrystal with Oxalic Acid. Cryst. Growth Des. 2008 8,1595-1598.
39. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals. Angew. Chem., Int. Ed. Engl. 1995 34, 1555-1573.
40. Fabelo, O.; Cañadillas-Delgado, L.; Delgado, F. S.; LorenzoLuis, P.; Laz, M.; Julve, M.; Ruiz-Pérez, M. C. Hydrogen BondDirected Frameworks Based on 1,2,4,5-Benzene-Tetracarboxylate. Cryst. Growth Des. 2005 5, 1163-1167.
41. Stahly, G. P. A Survey of Cocrystals Reported Prior to 2000. Cryst. Growth Des. 2009 9, 4212-4229.
42. Schultheiss, N.; Newman, A. Pharmaceutical Cocrystals and Their Physicochemical Properties. Cryst. Growth Des. 2009 9, 2950-2967.
43. Friščić, T.; Jones, W. Recent Advances in Understanding the Mechanism of Cocrystal Formation via Grinding. Cryst. Growth Des. 2009 9, 1621-1637.
44. Stahly, G. P. Diversity in Single- and Multiple-Component Crystals. The Search for Prevalence of Polymorphs and Cocrystals. Cryst. Growth Des. 2007 7, 1007-1026.
45. Chadwick, K.; Davey, R. J.; Dent, G.; Pritchard, R. G. Cocrystallization: A Solution Chemistry Perspective and the Case of Benzophenone and Diphenylamine. Cryst. Growth Des. 2009 9, 1990-1999.
46. Chadwick, K.; Davey, R.; Cross, R. How Does Grinding Produce Co-crystals? Insights from the Case of Benzophenone and Diphenylamine. Cryst. Growth Des. 2009 9,1990-1999.
47. Seaton, C. C.; Parkin, A.; Wilson, C. C.; Blagden, N. Growth of an Organic Co-Crystal upon a Component Subphase. Cryst. Growth Des. 2008 8, 363-368.
48. Basavoju, S.; Boström, D.; Velaga, S. P. Indomethacin-Saccharin Cocrystal: Design, Synthesis and Preliminary Pharmaceutical Characterization. Pharm. Res. 2008 25, 530-541.
49. Craven, B. M.; Gartland, G. L. Molecular Association of Barbital and Caffeine in 2:1 Crystalline Complex. J. Pharm. Sci. 1970 57, 1666-1610.
50. Du, M.; Zhang, Z.-H.; Zhao, X.-J. Cocrystallization of Trimesic Acid and Pyromellitic Acid with Bent Dipyridines. Cryst. Growth Des. 2005 5, 1247-1254.
51. Cooke, C. L.; Davey, R. J. On the Solubility of Saccharinate Salts and Cocrystals. Cryst. Growth Des. 2008 8, 3483-3485.
52. Rafilovich, M.; Bernstein, J.; Hickey, M. B.; Tauber, M. Benzidine: A Co-Crystallization Agent for Proton Acceptors. Cryst. Growth Des. 2007 7, 1777-1782.
53. Viertelhaus, M.; Hilfiker, R.; Blatter, F. Piracetam Co-crystals with OH-Group Functionalized Carboxylic Acids. Cryst. Growth Des. 2009 9, 2220-2228.
54. Sreekanth, B. R.; Vishweshwar, P.; Vyas, K. Supramolecular Synthon Polymorphism in 2:1 Co-crystal of 4-hydroxybenzoic Acid and 2,3,5,6- tetramethylpyrazine. Chem. Commun. 2007, 2375-2377.
55. Good, D. J.; Rodriguez-Hornedo, N. Solubility Advantage of Pharmaceutical Cocrystals. Cryst. Growth Des. 2009 9, 2252-2264.
56. Nehm, S. J.; Rodríguez-Spong, B.; Rodríguez-Hornedo, N. Phase Solubility Diagrams of Cocrystals are Explained by Solubility Product and Solution Complexation. Cryst. Growth Des. 2006 6, 592-600.
57. Rodriguez-Hornedo, N.; Nehm, S. J.; Seefeldt, K. F.; PagnTorres, Y.; Falkiewicz, C. J. Reaction Crystallization of Pharmaceutical Molecular Complexes. Mol.. Pharmaceutics 2006 3, 362-361.
58. Chiarella, R. A.; Davey, R. J.; Peterson, M. L. Making Co-Crystals - The Utility of Ternary Phase Diagrams. Cryst. Growth Des. 2007 7, 1223-1226.
59. Bethune, S. J.; Huang, N.; Jayasankar, A.; Rodríguez-Hornedo, N. Understanding and Predicting the Effect of Cocrystal Components and pH on Cocrystal Solubility. Cryst. Growth Des. 2009 9, 3976-3988.
60. Jayasankar, A.; Sreenivas Reddy, L.; Bethune, S. J.; Rodrí guezHornedo, N. Role of Cocrystal and Solution Chemistry on the Formation and Stability of Cocrystals with Different Stoichiometry. Cryst. Growth Des. 2009 9, 889-897.
61. Sheikh, A. Y.; Abd Rahim, S.; Hammond, R. B.; Roberts, K. J. Scalable Solution Cocrystallization: Case of CarbamazepineNicotinamide I. CrystEngComm 2009,11, 501-509.
62. Shan, N.; Zaworotko, M. J. The Role of Cocrystals in Pharmaceutical Science. Drug Discovery Today 2008 13, 440-446.
63. Thomas, R.; Kulkarni, G. U. Hydrogen Bonding in ProtonTransfer Complexes of Cytosine with Trimesic and Pyromellitic Acids. J. Mol. Struct. 2008 873, 160-167.
64. Takenaka, A.; Sasada, Y. Elementary Patterns in Protein-Nucleic Acid Interactions. III. Crystal Structure of Adenine :Phthalic Acid (3:1) Complex Hydrate. Bull. Chem. Soc. Jpn. 1982 55, 680-686.
65. Perumalla, S. R.; Suresh, E.; Pedireddi, V. R. Nucleobases in Molecular Recognition: Molecular Adducts of Adenine and Cytosine with COOH Functional Groups. Angew. Chem., Int. Ed. 2005 44, 7752-7757.
66. Sivakova, S.; Rowan, S. J. Nucleobases as Supramolecular Motifs. Chem. Soc. Rev. 2005 34, 9-21.
67. Fujita, S.; Takenaka, A.; Sasada, Y. Crystal Structure of Adenine1-(2-Carboxyethyl)uracil (1:1) Complex. A Model for Interactions of Amino Acid Side Chains with Nucleic Acid Base Pair. Bull. Chem. Soc. Jpn. 1983 56, 2234-2237.
68. Tamura, C.; Sakurai, N.; Sato, S. Studies on Intermolecular Complex Formation. I. Between Nucleotide Bases and Organic Compounds. Bull. Chem. Soc. Jpn. 1971 44,1473-1479.
69. Ohki, M.; Takenaka, A.; Shimanouchi, H.; Sasada, Y. Complexes between Nucleotide Base and Amino Acid. I. Crystal Structure of Cytosine: N-Formylglycine. Bull. Chem. Soc. Jpn. 1975 48, 848-852.
70. Barker, D. L.; Marsh, R. E. The Crystal Structure of Cytosine. Acta Crystallogr. 1964 17, 1581-1587.
71. Jeffrey, G. A.; Kinoshita, Y. The Crystal Structure of Cytosine Monohydrate. Acta Crystallogr. 1963 16, 20-28.
72. Peräkylä, M. A Model Study of the Enzyme-Catalyzed Cytosine Methylation Using ab Initiio Quantum Mechanical and Density Functional Theory Calculations: pKa of the Cytosine N3 in the Intermeditaes and Transition States of the Reaction. J. Am. Chem. Soc. 1998 120,12895-12902.
73. Shattock, T. R.; Arora, K. K.;Vishweshwar, P.; Zaworotko, M. J. Hierarchy of Supramolecular Synthons: Persistent Carboxylic Acid ⋯ Pyridine Hydrogen Bonds in Cocrystals that also Contain a Hydroxyl Moiety. Cryst. Growth Des. 2008 8, 4533-4545.
74. Aakeröy, C. B.; Desper, J.; Leonard, B.; Urbina, J. F. Toward High-Yielding Supramolecular Synthesis: Directed Assembly of Ditopic Imidazoles/Benzimidazoles and Dicarboxylic Acids into Cocrystals via Selective O-H ⋯ N Hydrogen Bonds. Cryst. Growth Des. 2005 5, 865-873.
75. Trask, A. V.; Sam Motherwell, W. D.; Jones, W. Physical Stability Enhancement of Theophylline via Cocrystallization. Int. J. Pharm. 2006 320, 114-123.
76. Trask, A. V.; Samuel Motherwell, W. D.; William, J. Pharmaceutical Cocrystallization: Engineering a Remedy for Caffeine Hydration. Cryst. Growth Des. 2005 5, 1013-1021.
77. Strathmann, T. J.; Myneni, S.C.B. Speciation of Aqueous Ni(II)Carboxylate and Ni(II)-Fulvic Acid Solutions: Combined ATRFTIR and XAFS Analysis. Geochim. Cosmochim. Acta 2004 68, 3441-3458.
78. Friščić, T.; Trask, A. V.; Motherwell, W. D. S.; Jones, W. GuestDirected assembly of Caffeine and Succinic Acid into Topologically Different Heteromolecular Host Networks Upon Grinding. Cryst. Growth Des. 2008 8, 1605-1609.
79. García-Terán, J. P.; Castillo, O.; Luque, A.; García-Couceiro, U.; Beobide, G.; Román, P. Molecular Recognition of Protonated Cytosine Ribbons by Metal-Oxalato Frameworks. Cryst. Growth Des. 2007 7, 2594-2600.
80. Takeda, Y.; Ohlendorf, D. H. DNA-Binding Proteins. Science 1983 221, 1020-1026.
81. Pabo, C. O. Protein-DNA Recognition. Annu. Rev. Biochem. 1984 53, 293-321.
82. Sulkowska, A. Physical Aspects of the Interaction of Pyrimidine and Purine Bases with Proteins. Spectroscopy 2002 16, 379-385.
83. Sellergren, B. Imprinted Polymers with Memory for Small Molecules, Proteins, or Crystals. Angew. Chem., Int. Ed. 2000 39, 1031-1037.
84. Valeur, B. Characteristics of Fluorescence Emission, In Molecular Fluorescence: Principles and Applications; Wiley-VCH: New York, 2002; Chapter 3, pp 34-71.
85. Murakami, A.; Konishi, Y.; Shimidzu, T. Syntheses and Properties of Poly(iminoethylene) Derivatives Containing Nucleotide Moieties. Makromol. Chem. 1980 181, 2229-2236.
86. Blatchford, J. W.; Jessen, S. W.; Lin, L.-B.; Gustafson, T. L.; Fu, D.-K.; Wang, H.-L.; Swager, T. M.; MacDiarmid, A. G. Photoluminescence in Pyridine-Based Polymers: Role of Aggregates. Phys. Rev. B 1996 54, 9180-9189.
87. Wong, K. T.; Liao, Y. L.; Wu, C. C.; Lin, Y. T.; Chiang, H. H. Echem Hightech Co. Ltd. Pyrimidine Spirobifluorene Oligomer for Organic Light Emitting Device. U.S. Patent No. 6872824 B2, 2005.
88. Craven, B. M.; McClure, R. J. New Investigations of Cytosine and Its Monhydrate. Acta Crystallogr. 1973 B29, 1234-1238.
89. Lee, T.; Lin, M. S. Sublimation Point Depression of Tris(8hydroxyquinoline)aluminum(III) (Alq3) by Crystal Engineering. Cryst. Growth Des. 2007 7, 1803-1810.
90. Basavoju, S.; Boström, D.; Velaga, S. P. Pharmaceutical Cocrystal and Salts of Norfloxacin. Cryst. Growth Des. 2006 6, 2699-2708.
91. Johnson, S. L.; Rumon, K. A. Infrared Spectra of Solid 1:1 Pyridine-Benzoic Acid Complexes; the Nature of the Hydrogen Bond as a Function of the Acid-Base Levels in the Complex. J. Phys. Chem. 1965 69, 74-86.
92. Smith, G.; Lynch, D. E.; Byriel, K. A.; Kennard, C. H. L. The Utility of 4-Aminobenzoic Acid in Promotion of Hydrogen Bonding in Crsytallization Processes: the Structures of the Cocrystals with Halo and Nitro Substituted Aromatic Compounds, and the Crystal Structures of the Adducts with 4-Nitroaniline (1:1), 4-(4-Nitrobenzyl)pyridine (1:2), and (4-Nitrophenyl)acetic Acid (1:1). J. Chem. Crystallogr. 1997 27, 307-317.
93. Fürtig, B.; Richter, C.; Wöhnert, J.; Schwalbe, H. NMR Spectroscopy of RNA. ChemBioChem 2003 4, 936-962.
94. Clawson, J. S.; Vogt, F. G.; Brum, J.; Sisko, J.; Patience, D. B.; Dai, W.; Sharpe, S.; Jones, A. D.; Pham, T. N.; Johnson, M. N.; Copley, R. C. P. Formation and Characterization of Crystals Containing a Pleuromutilin Derivative, Succinic Acid and Water. Cryst. Growth Des. 2008 8,4120-4131.
95. 15N NMR Spectroscopy. J. Am. Chem. Soc. 2006128, 8199-8210.
96. 15N Solid-State NMR Studies of Imidazole- and Morpholine-Based Model Compounds Possessing Halogen and Hydrogen Bonding Capabilities. Cryst. Growth Des. 2008 8, 3941-3950.
97. Childs, S. L.; Patrick Stahly, G.; Park, A. The Salt-Cocrystal Continuum: The Influence of Crystal Structure on Ionization State. Mol. Pharmaceutics 2007 4, 323-338.
98. Colthup, N. B.; Daly, L. H.; Wiberley, S. E. In Introduction to Infrared and Raman Spectroscopy, 3rd ed.; Academic Press, Inc.: New York, 1990; Chapters 5 and 9, pp 227, 313-318, 340-341.
99. Hollenbeck, R. G. Determination of Differential Heat of Solution in Real Solutions from Variation in Solubility with Temperature. J. Pharm. Sci. 1980 69, 1241-1242.
100. Topal, M. D.; Fresco, J. R. Complementary Base Pairing and the Origin of Substitution Mutations. Nature 1976 263, 285-293.
101. Guschlbauer, W. Protonated Polynucleotide Structures, I. The Thermal Denaturation of Polycytidylic Acid in Acid Solution. Proc. Nat. Acad. Sci. U.S.A. 196757, 1441-1448.
102. Saenger, W. Forces Stabilizing Associations Between Bases: Hydrogen Bonding and Base Stacking, In Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984; Chapter 6, pp 118-124.
103. Perumalla, S. R.; Suresh, E.; Pedireddi, V. R. Nucleobases in Molecular Recognition: Molecular Adducts of Adenine and Cytosine with COOH Functional Groups. Angew. Chem., Int. Ed. 2005 44, 7752-7757.
104. Sreenivas Reddy, L.; Bethune, S. J.; Kampf, J. W.; RodriguezHornedo, N. Cocrystals and Salts of Gabapentin: pH Dependent Cocrystal Stability and Solubility. Cryst. Growth Des. 2009 9, 378-385.
105. Cowan, J. A.; Howard, J. A. K.; McIntyre, G. J.; Lo, S. M.- F.; Williams, I. D. Variable-Temperature Neutron Diffraction Studies of the Short, Strong N⋯ O Hydrogen Bonds in the 1:2 Co-crystal of Benzene-1,2,4,5- Tetracarboxylic Acid and 4,4′-bipyridyl. Acta Crystallogr. 2003 B59, 794-801.
106. Portalone, G.; Colapietro, M. Solid-Phase Molecular Recognition of Cytosine Based on Proton-Transfer Reaction. J. Chem. Crystallogr. 2009 39, 193-200.
107. Ataka, K.; Osawa, M. In Situ Infrared Study of Cytosine Adsorption on Gold Electrodes. J. Electroanal. Chem. 1999 460, 188-196.