Crystalline structure of N-(S)-2-heptyl (1R,2R)-2-(2,3- anthracenedicarboximido)cyclohexanecarboxamide that differs from its preferred conformation in the solvent used for crystallization

Bioscience, Biotechnology and Biochemistry

Volumn 69, Issue 10, 2005, Pages 2002-2004

  Akasaka, Kazuaki ^a   Ohtaki, Takashi ^a   Kabuto, Chizuko ^a   Kitahara, Takeshi ^b   Ohrui, Hiroshi ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b KITASATO INSTITUTE   (Japan)

Author keywords

Chiral reagent; Crystalline structure; Fluorescent reagent; N (S) 2 heptyl (1R, 2R) 2 (2,3 anthracenedicarboximido)cyclohexanecarboxamide

Indexed keywords

CONFORMATIONS; CRYSTAL STRUCTURE; CRYSTALLINE MATERIALS; CRYSTALLIZATION; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; X RAY ANALYSIS;

CHIRAL REAGENT; CRYSTAL PACKING; CRYSTALLINE STRUCTURE; FLUORESCENT REAGENT;

AMINES;

AMIDE; ANTHRACENE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; N (S) 2 HEPTYL (1R,2R) 2 (2,3 ANTHRACENEDICARBOXIMIDO)CYCLOHEXAMIDE; N-(S)-2-HEPTYL (1R,2R)-2-(2,3-ANTHRACENEDICARBOXIMIDO)CYCLOHEXAMIDE;

ARTICLE; CHEMISTRY; CONFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

AMIDES; ANTHRACENES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; SOLUTIONS; STEREOISOMERISM;

EID: 27644444020     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.69.2002     Document Type: Article

References (8)

1. Buevich, A. V., Chan, T.-M., Wang, C. H., McPhail, A. T., and Ganguly, A. K., Structure determination and conformation analysis of symmetrical dimers. Magnetic Resonance in Chemistry, 43, 187-199 (2005).
2. Wang, F., Polavarapu, P. L., Drabowicz, J., Kielbasinski, P., Mikolajczyk, M., Wieczorek, N. W., Majzner, W. W., and Lazewska, I., Solution and crystal structures of chiral molecules can be significantly different: tert-butylphenyl-phosphinoselenoic acid. J. Phys. Chem. A, 108, 2072-2079 (2004).
3. Imaizumi, K., Terashima, H., Akasaka, K., and Ohrui, H., Highly potent chiral labeling reagent for the discrimination of chiral alcohols. Anal. Sci., 19, 1243-1249 (2003).
4. Mori, K., Ohtaki, T., Ohrui, H., Berkebile, D. R., and Carlson, D. A., Synthesis of the four stereoisomers of 6-acetoxy-19-methylnonacosane, the most potent component of the female sex pheromone of the new world screwworm fly, with special emphasis on partial racemization in the course of catalytic hydrogenation. Eur. J. Org. Chem., 1089-1096 (2004).
5. 1H-NMR and HPLC after labeling with a chiral derivatization reagent, 2-(2,3-anthracenedicarboximide)cyclohexane carboxylic acid. Chirality, 17, S171-S176 (2005).
6. Nishio, M., and Hirota, M., CH/π interaction: Implications in organic chemistry. Tetrahedron, 45, 7201-7245 (1989).
7. Suezawa, H., Mori, A., Sato, M., Ehama, R., Akai, I., Sakakibara, K., Hirota, M., Nishio, M., and Kodama, Y., Evidence for the presence of the CH-π-interacted apconformers of benzyl formates. J. Phys. Org. Chem., 6, 399-406 (1993).
8. Benjamin, W. G., Zhaohai, Z., and Rebecca, A. F., Conformational study of 1,5-hexadiene and 1,5-diene-3,4-diols. J. Am. Chem. Soc., 117, 1783-1788 (1995).