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Molecules 2015, 20(7), 12880-12900; doi:10.3390/molecules200712880

Characteristic Conformation of Mosher’s Amide Elucidated Using the Cambridge Structural Database

1
Division of Insect Sciences, National Institute of Agrobiological Sciences, Tsukuba, Ibaraki 305-8634, Japan
2
Analytical Science Division, National Food Research Institute, Tsukuba, Ibaraki 305-8642, Japan
3
Department of Chemistry, Biology, and Environmental Science, Faculty of Science, Nara Women's University, Kita-Uoya Nishi-machi, Nara 630-8506, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 23 June 2015 / Revised: 9 July 2015 / Accepted: 10 July 2015 / Published: 16 July 2015
(This article belongs to the Section Molecular Diversity)
View Full-Text   |   Download PDF [937 KB, uploaded 16 July 2015]   |  

Abstract

Conformations of the crystalline 3,3,3-trifluoro-2-methoxy-2-phenylpropanamide derivatives (MTPA amides) deposited in the Cambridge Structural Database (CSD) were examined statistically as Racid-enantiomers. The majority of dihedral angles (48/58, ca. 83%) of the amide carbonyl groups and the trifluoromethyl groups ranged from –30° to 0° with an average angle θ1 of −13°. The other conformational properties were also clarified: (1) one of the fluorine atoms was antiperiplanar (ap) to the amide carbonyl group, forming a staggered conformation; (2) the MTPA amides prepared from primary amines showed a Z form in amide moieties; (3) in the case of the MTPA amide prepared from a primary amine possessing secondary alkyl groups (i.e., Mosher-type MTPA amide), the dihedral angles between the methine groups and the carbonyl groups were syn and indicative of a moderate conformational flexibility; (4) the phenyl plane was inclined from the O–Cchiral bond of the methoxy moiety with an average dihedral angle θ2 of +21°; (5) the methyl group of the methoxy moiety was ap to the ipso-carbon atom of the phenyl group. View Full-Text
Keywords: chiral recognition; chirality; crystal engineering; Mosher’s method; MTPA chiral recognition; chirality; crystal engineering; Mosher’s method; MTPA
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ichikawa, A.; Ono, H.; Mikata, Y. Characteristic Conformation of Mosher’s Amide Elucidated Using the Cambridge Structural Database. Molecules 2015, 20, 12880-12900.

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