Thermochemistry and conformational polymorphism of a hexamorphic crystal system

Journal of the American Chemical Society

Volumn 122, Issue 4, 2000, Pages 585-591

  Yu, Lian ^a   Stephenson, Gregory A ^a   Mitchell, Christine A ^a   Bunnell, Charles A ^a   Snorek, Sharon V ^a   Bowyer, J Joe ^a   Borchardt, Thomas B ^b,c   Stowell, Joseph G ^b   Byrn, Stephen R ^b  

^a ELI LILLY AND COMPANY   (United States)

^b PURDUE UNIVERSITY   (United States)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CRYSTALLIZATION; DIPOLE; HYDROGEN BOND; MELTING POINT; MOLECULAR STABILITY; THERMODYNAMICS;

EID: 0033966871     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9930622     Document Type: Article

References (43)

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15. See Supporting Information. Gavezzotti and Fillippini found 163 polymorphic systems whose structures have been solved at the room temperature, in which 13 have three polymorphs, three have four, and none have five or more. Reports of extensive polymorphism can be found in the thermomicroscopy literature (for example, Kuhnert-Brandstatter, M. Thermomicroscopy in the analysis of pharmaceuticals. Oxford: Pergamon Press, 1971). However, some are transient phases observed during heating or cooling without crystallographic conformation. The polymorphism of 1 is distinguished by the number of polymorphs that are stable essentially indefinitely at the room temperature to allow crystallographic and other analyses.
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21. Previously (ref 16), we designated Form ON simply as O, because Form OP, also orange-colored, was then unknown.
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30. We stated previously that hydrogen bonding is exclusively intramolecular (ref 16). However, reexamination of the structures revealed a weak intermolecular hydrogen bond in Form Y.
31. Y)]/T.
32. -1 in o-aminobenzonitrile (Pouchert, C. J. The Aldrich Library of FT-IR Spectra; Aldrich Chemical Co.: Milwaukee, 1985).
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34. Spartan 5.0; Wavefunction, Inc., 18401 Van Karman Ave., #370: Irvine, CA 92715.
35. nitro fixed. We considered results thus obtained as a "true" measure of conformational energies of molecules observed in different polymorphs.
36. Y) (259.29 g/mol) = 0.24 J/mol, which is much smaller than the ΔH values (several kJ/mol, see Table 4).
37. Peterson, M. L.; Strnad, J. T.; Markotan, T. P.; Morales, C. A.; Scaltrito, V.; Staley, S. W. J. Org. Chem. 1999, 64, 9067-9076.
38. g was measured by DSC at 10°C/min using the standard melt/quench technique.
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42. Borchardt, T. Ph.D. Thesis, Purdue University, 1997.
43. This energy difference is much smaller than the expected 10-20 kJ/mol from the formation of an intermolecular N-H⋯N bond (see, for example: Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond; W. H. Freeman & Co.: San Francisco, 1960).