The thermodynamically stable form of solid barbituric acid: The enol tautomer

Angewandte Chemie - International Edition

Volumn 50, Issue 34, 2011, Pages 7924-7926

  Schmidt, Martin U ^a   Brüning, Jürgen ^a   Glinnemann, Jürgen ^a   Hützler, Maximilian W ^a   Mörschel, Philipp ^a   Ivashevskaya, Svetlana N ^d   Van De Streek, Jacco ^e   Braga, Dario ^b   Maini, Lucia ^b   Chierotti, Michele R ^c   Gobetto, Roberto ^c  

^a GOETHE UNIVERSITY   (Germany)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF TURIN   (Italy)

^d Russian Academy of Sciences   (Russian Federation)

^e Avant garde Materials Simulation   (Germany)

Author keywords

barbituric acid; lattice energy minimizations; neutron diffraction; NMR spectroscopy; tautomerism

Indexed keywords

BARBITURIC ACID; LATTICE-ENERGY MINIMIZATIONS; POLYMORPHIC PHASIS; ROOM TEMPERATURE; TAUTOMERIC FORMS; TAUTOMERISM; THERMODYNAMICALLY STABLE;

DIFFRACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HYDROGEN BONDS;

EID: 80051768921     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101040     Document Type: Article

References (22)

1. A. Baeyer, Justus Liebigs Ann. Chem. 1864, 131, 291-302.
2. F. Zuccarello, G. Buemi, C. Gandolfo, A. Contino, Spectrochim. Acta Part A 2003, 59, 139-151
3. V. B. Delchev, J. Struct. Chem. 2004, 45, 570-578
4. S. Ralhan, N. K. Ray, J. Mol. Struct. 2003, 634, 83-88.
5. K. Senthilkumar, P. Kolandaivel, J. Comput.-Aided Mol. Des. 2002, 16, 263-272
6. M. Eigen, G. Ilgenfritz, W. Kruse, Chem. Ber. 1965, 98, 1623-1638.
7. W. Bolton, Acta Crystallogr. 1963, 16, 166-173
8. T. C. Lewis, D. A. Tocher, S. L. Price, Cryst. Growth Des. 2004, 4, 979-987.
9. N. Zencirci, E. Gstrein, C. Langes, U. J. Griesser, Thermochim. Acta 2009, 485, 33-42
10. M. V. Roux, M. Temprado, R. Notario, C. Foces-Foces, V. N. Emel'yanenko, S. P. Verevkin, J. Phys. Chem. A 2008, 112, 7455-7465
11. D. Braga, M. Cadoni, F. Grepioni, L. Maini, K. Rubini, CrystEngComm 2006, 8, 756-763.
12. G. S. Nichol, W. Clegg, Acta Crystallogr. Sect. B 2005, 61, 464-472
13. G. A. Jeffrey, S. Ghose, J. O. Warwicker, Acta Crystallogr. 1961, 14, 881-887.
14. M. R. Chierotti, R. Gobetto, L. Pellegrino, L. Milone, P. Venturello, Cryst. Growth Des. 2008, 8, 1454-1457
15. Tautomeric polymorphism of 2-thiobarbituric acid has been observed:, M. R. Chierotti, L. Ferrero, N. Garino, R. Gobetto, L. Pellegrino, D. Braga, F. Grepioni, L. Maini, Chem. Eur. J. 2010, 16, 4347-4358
16. A recent survey on polymorphic tautomers is given by: A. J. Cruz-Cabeza, C. R. Groom, CrystEngComm 2011, DOI:.
17. Program DASH, see:, W. I. F. David, K. Shankland, J. van de Streek, E. Pidcock, W. D. S. Motherwell, J. C. Cole, J. Appl. Crystallogr. 2006, 39, 910-915.
18. A. A. Coelho: TOPAS-Academic Version 4.1, Coelho Software, Brisbane, Australia.
19. G. Gilli, F. Bellucci, V. Ferretti, V. Bertolasi, J. Am. Chem. Soc. 1989, 111, 1023-1028.
20. M. R. Chierotti, R. Gobetto, Chem. Commun. 2008, 1621-1634.
21. M. A. Neumann, Program GRACE, http://www.avmatsim.eu
22. G. Kresse, J. Hafner, Phys. Rev. B 1993, 47, 558-561.