Crystallization of Pseudopolymorphs of Some Gamboge Pigments. Pyridine, Dimethylformamide and Dimethylsulfoxide Solvates of Morellic Acid, Gambogic Acid and Guttiferic Acid

References

• Myerson , A. S. , Green , D. A. and Meenan , P. , eds. 1996 . “ Crystal Growth of Organic Materials ” . In ACS Conference Proceedings Series , Washington, D.C. : American Chemical Society .
   Google Scholar
• Desiraju , G. R. 1997 . Science , 278 : 404
   Web of Science ®Google Scholar
• Addadi , L. , Berkovitch-Yellin , Z. , Weissbuch , I. , van Mil , J. , Shimon , L. J. W. , Lahav , M. and Leiserowitz , L. 1985 . Angew. Chem. Int. Ed. Engl , 24 : 466 Papers that deal with the relationship between organic crystal quality and chemical (structural) factors are not common. A selected list of papers that mention methods of improving crystal quality are given here with the method proposed in each case. Some of these methods are specific to the systems studied: (a). Tailor-made impurities;
   Web of Science ®Google Scholar
• Etter , M. C. and Baures , P. W. 1988 . J. Am. Chem. Soc. , 110 : 639 Triphenylphosphine oxide as a complexing agent;
   Web of Science ®Google Scholar
• Dance , I. G. 1996 . “ The Crystal as a Supramolecular Entity ” . In Perspectives in Supramolecular Chemistry , Edited by: Desiraju , G. R. Vol. 2 , 137 – 233 . Chichester : Wiley . The ‘phenyl factor’ that derives from the presence of triphenyl residues in the molecule;
   Google Scholar
• Pedireddi , V. R. , Jones , W. , Chorlton , A. P. and Docherty , R. 1996 . Chem. Commun. , : 997 Molecular complexation;
   Google Scholar
• Madhavi , N. N. L. , Katz , A. K. , Carrell , H. L. , Nangia , A. and Desiraju , G. R. 1997 . Chem. Commun. 1953. Use of specific solvents;
   Google Scholar
• Görbitz , C. H. and Torgersen , E. 1999 . Acta Crystallogr. , B55 : 104 Relationship between type of hydrogen bond network and crystal quality.
   Google Scholar
• Venkataraman , K. 1973 . Pigments of Garcinia species , New Delhi : Indian National Science Academy .
   Google Scholar
• Kartha , G. , Ramachandran , G. N. , Bhat , H. B. , Nair , P. M. , Raghavan , V. K. V. and Venkataraman , K. 1963 . Tetrahedron Lett. , 7 : 459
   Google Scholar
• Rao , K. V. N. and Rao , P. L. N. 1961 . Experientia , 17 : 213
   Google Scholar
• Gupta , V. S. , Rao , P. L. N. , Vaidya , S. N. and Ramaseshan , S. 1962 . Chem. and Ind. , : 1469
   Google Scholar
• Rao , D. R. 1955 . Bangalore : Indian Institute of Science . A. I. I. Sci. Thesis
   Google Scholar
• Santhanam , K. 1967 . Bangalore : Indian Institute of Science . Ph. D. Thesis
   Google Scholar
• Threlfall , T. L. 1995 . Analyst , 120 : 2435 By ‘pseudopolymorphism’, we refer to the phenomenon wherein a compound is obtained in crystalline forms that differ in the nature or stoichiometry of included solvent molecules. See (a).
   Web of Science ®Google Scholar
• Bernstein , J. “ Organic Solid State Chemistry ” . In Studies in Organic Chemistry , Edited by: Desiraju , G. R. Vol. 32 , 471 – 518 . Amsterdam : Elsevier .
   Google Scholar
• Sheldrick , G. M. 1997 . Program for crystal structure solution and refinement , Germany : University of Göttingen . SHELX-97
   Google Scholar
• These and other hydrogen bond geometries are neutron-normalized.
   Google Scholar
• Takasuka , M. , Nakai , H. and Shiro , M. 1982 . J. Chem. Soc., Perkin Trans. , 2 : 1061
   Google Scholar
• Weber , E. J. 1989 . Mol. Graphics , 7 : 12
   Google Scholar
• Desiraju , G. R. 1991 . Acc. Chem. Res. , 24 : 270
   Google Scholar
• Chaney , J. D. , Goss , C. R. , Folting , K. , Santarsiero , B. D. and Hollingsworth , M. D. 1996 . J. Am. Chem. Soc. , 118 : 9432
   Web of Science ®Google Scholar
• Desiraju , G. R. and Steiner , T. 1999 . The Weak Hydrogen Bond in Structural Chemistry and Biology , Oxford : Oxford University Press .
   Google Scholar
• Desiraju , G. R. 1996 . Acc. Chem. Res. , 29 : 441
   PubMed Web of Science ®Google Scholar
• Steiner , T. 1996 . Cryst. Rev. , 6 : 1
   Google Scholar
• Csöregh , I. , Gallardo , O. , Weber , E. , Pollex , R. and Dörpinghaus , N. 1995 . J. Incl. Phen. Mol. Recog. Chem. , 20 : 253
   Google Scholar
• Kaduk , J. A. , Cahill , P. J. and Venkateshwaran , L. N. 1999 . J. Appl. Cryst. , 32 : 15 However, for the crystal structure of a very unusual dmso solvate see
   Google Scholar
• Nangia , A. and Desiraju , G. R. 1999 . Chem. Commun. , : 605 This study shows that dmso is included about five times more often than might have been expected on the basis of its usage as a recrystallizing solvent, and that in most of the cases wherein the solute contains O/N—H groups, the solvent forms C—H…O hydrogen bonds in addition to stronger O/N—H…O bonds.
   Google Scholar
• Leiserowitz , L. 1976 . Acta Crystallogr. , B32 : 775
   Web of Science ®Google Scholar
• Payne , R. S. , Roberts , R. J. , Rowe , R. C. and Docherty , R. 1998 . J. Comput. Chem. , 19 : 1
   Google Scholar
• Mooij , W. T. M. , van Eijck , B. P. , Price , S. L. , Verwer , P. and Kroon , J. 1998 . J. Comput. Chem. , 19 : 459
   Web of Science ®Google Scholar
• Kuduva , S. S. , Craig , D. C. , Nangia , A. and Desiraju , G. R. 1999 . J. Am. Chem. Soc. , 121 : 1936
   Web of Science ®Google Scholar
• Luger , P. 1998 . Angew. Chem. Int. Ed. Engl. , 37 : 3353
   Google Scholar