Determination of the rotational barrier for kinetically stable conformational isomers via NMR and 2D TLC. An Introductory organic chemistry experiment

Journal of Chemical Education

Volumn 84, Issue 9, 2007, Pages 1499-1501

  Rushton, Gregory T ^a   Burns, William G ^a   Lavin, Judi M ^a   Chong, Yong S ^a   Pellechia, Perry ^a   Shimizu, Ken D ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; CONDENSATION REACTIONS; CONFORMATIONS; ENERGY BARRIERS; NUCLEAR MAGNETIC RESONANCE; RATE CONSTANTS; SYNTHESIS (CHEMICAL); THIN LAYER CHROMATOGRAPHY;

ORGANIC CHEMISTRY; ROTATIONAL BARRIER; STEREOISOMER;

ISOMERS;

EID: 34548605794     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed084p1499     Document Type: Article

References (8)

1. Brown, W. H.; Foote, C. S. Organic Chemistry, 3rd ed.; Harcourt College Publishers: Orlando, FL, 2002; pp 65-83.
2. In contrast, previous submissions to JCE have studied systems with much lower barriers that require more advanced theory and techniques than is appropriate for an introductory organic course. Jarek, R. L.; Flesher, R. J.; Shin, S. K. J. Chem. Educ. 1997, 74, 978-982.
3. Gasparro, F. P.; Kolodny, N. H. J. Chem. Educ. 1977, 54, 258-261.
4. Morris, K. F.; Erikson, L. E. J. Chem. Educ. 1996, 73, 471-473.
5. Choi, D.-S.; Chong, Y. S.; Whitehead, D.; Shimizu, K. D. Org. Lett. 2001, 23, 3757-3760.
6. Chong, Y. S.; Smith, M. D.; Shimizu, K. D. J. Am. Chem. Soc. 2001, 123, 7463-7464.
7. Chen, Y.; Smith, M. D.; Shimizu, K. D. Tetrahedron Lett. 2001, 42, 7185-7187.
8. Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1970, 70 (5), 517-551.