3-Methylcyclohexanone thiosemicarbazone: Determination of E/Z isomerization barrier by dynamic high-performance liquid chromatography, configuration assignment and theoretical study of the mechanisms involved by the spontaneous, acid and base catalyzed processes

Journal of Chromatography A

Volumn 1269, Issue , 2012, Pages 168-177

  Carradori, Simone ^a   Cirilli, Roberto ^b   Dei Cicchi, Simona ^a   Ferretti, Rosella ^b   Menta, Sergio ^b   Pierini, Marco ^a   Secci, Daniela ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

Ab initio calculations; Chiralpak AS H; Chiralpak IA; Configuration assignment; Dynamic HPLC; E Z isomerization; Isomer separation

Indexed keywords

AB INITIO CALCULATIONS; CHIRALPAK; CHIRALPAK IA; CONFIGURATION ASSIGNMENT; ISOMER SEPARATION;

CHROMATOGRAPHY; FACTOR ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERIZATION; RATE CONSTANTS; STEREOCHEMISTRY;

ISOMERS;

3 METHYLCYCLOHEXANONE THIOSEMICARBAZONE; ACID; BASE; POLYSACCHARIDE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CIRCULAR DICHROISM; CONTROLLED STUDY; DIASTEREOISOMER; ELUTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERIZATION; PRIORITY JOURNAL; PROCESS OPTIMIZATION; SEPARATION TECHNIQUE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THEORETICAL STUDY;

ACIDS; ALKALIES; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ISOMERISM; MODELS, MOLECULAR; MODELS, THEORETICAL; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; THIOSEMICARBAZONES;

EID: 84870314704     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2012.08.007     Document Type: Article

References (35)

1. Shainaz Landge M., Aprahamian I. J. Am. Chem. Soc. 2009, 131:18269.
2. Wang M., Wang L.F., Li Y.Z., Li Q.X., Xu Z.D., Qu D.M. Trans. Met. Chem. 2001, 26:307.
3. Yadav L.D.S., Singh S. Indian J. Chem. 2001, 40B:440.
4. Liu M.C., Lin T.S., Cory J.G., Cory A.H., Sartorelli A.C. J. Med. Chem. 1996, 39:2586.
5. Quiroga A.G., Perez J.M., Lopez-Solera I., Masaguer J.R., Luque A., Roman P., Edwards A., Alonso C., Navarro-Ranninger C. J. Med. Chem. 1998, 41:1399.
6. Belicchi-Ferrari M., Bisceglie F., Casoli C., Durot S., Morgenstern-Badarau I., Pelosi G., Pilotti E., Pinelli S., Tarasconi P. J. Med. Chem. 2005, 48:1671.
7. Tarasconi P., Capacchi S., Pelosi G., Cornia M., Albertini R., Bonati A., Dall'Aglio P.P., Lunghi P., Pinelli S. Bioorg. Med. Chem. 2000, 8:157.
8. Cirilli R., Ferretti R., La Torre F., Secci D., Bolasco A., Carradori S., Pierini M. J. Chromatogr. A 2007, 1172:160.
9. Asano T., Furuta H., Hofmann H.-J., Cimiraglia R., Tsuno Y., Fujiol M. J. Org. Chem. 1993, 58:4418.
10. Gálvez J., Guirado A. J. Comp. Chem. 2009, 31:520.
11. Johnson J.E., Morales N.M., Gorczyca A.M., Dolliver D.D., McAllister M.A. J. Org. Chem. 2001, 66:7979.
12. Chimenti F., Secci D., Bolasco A., Chimenti P., Granese A., Carradori S., Yanez M., Orallo F., Sanna M.L., Gallinella B., Cirilli R. J. Med. Chem. 2010, 53:6516.
13. Villani C., Pirkle W.H. Tetrahedron: Asymmetry 1995, 6:1.
14. Gasparrini F., Lunazzi L., Mazzanti A., Pierini M., Pietrusiewicz K.M., Villani C. J. Am. Chem. Soc. 2000, 122:4776.
15. Dell'Erba C., Gasparrini F., Grilli S., Lunazzi L., Mazzanti A., Novi M., Pierini M., Tavani C., Villani C. J. Org. Chem. 2002, 67:1663.
16. Gasparrini F., Grilli S., Leardini R., Lunazzi L., Mazzanti A., Nanni D., Pierini M., Pinamonti M. J. Org. Chem. 2002, 67:3089.
17. Dalla Cort A., Gasparrini F., Lunazzi L., Mandolini L., Mazzanti A., Pasquini C., Pierini M., Rompietti R., Schiaffino L. J. Org. Chem. 2005, 70:8877.
18. Cirilli R., Costi R., Di Santo R., La Torre F., Pierini M., Siani G. Anal. Chem. 2009, 81:3560.
19. Cabri W., D'Acquarica I., Simone P., Di Iorio M., Di Mattia M., Gasparrini F., Giorgi F., Mazzanti A., Pierini M., Quaglia M., Villani C. J. Org. Chem. 2011, 76:1751.
20. Cabri W., D'Acquarica I., Simone P., Di Iorio M., Di Mattia M., Gasparrini F., Giorgi F., Mazzanti A., Pierini M., Quaglia M., Villani C. J. Org. Chem. 2011, 76:4831.
21. Lunazzi L., Mancinelli M., Mazzanti A., Pierini M. J. Org. Chem. 2010, 75:5927.
22. Keller R.A., Giddings J.C. J. Chromatogr. 1960, 3:205.
23. Kramer R. J. Chromatogr. 1975, 107:241.
24. Schurig V., Bürkle W. J. Am. Chem. Soc. 1982, 104:7573.
25. Bürkle W., Karfunkel H., Schurig V. J. Chromatogr. 1984, 288:1.
26. Veciana J., Crespo M.I. Angew. Chem. Int. Ed. Engl. 1991, 30:74.
27. Jung M. QCPE Bull. 1992, 12:52.
28. Cabrera K., Jung M., Fluck M., Schurig V. J. Chromatogr. A 1996, 731:315.
29. Oxelbark J., Allenmark S. J. Org. Chem. 1999, 64:1483.
30. Trapp O., Schoetz G., Schurig V. Chirality 2001, 13:403.
31. Wolf C. Chem. Soc. Rev. 2005, 34:595.
32. Trapp O. Anal. Chem. 2006, 78:189.
33. D'Acquarica I., Gasparrini F., Pierini M., Villani C., Zappia G. J. Sep. Sci. 2006, 29:1508.
34. Uray G., Jahangir S., Fabian W.M.F. J. Chromatogr. A 2010, 1217:1017.
35. Roussel C., Del Rio A., Sanders J.P., Piras P., Vanthuyne N. J. Chromatogr. A 2004, 1037:311.